(+)-薄荷酮 | 3391-87-5

• 物质功能分类: 分析化学 - 分析试剂 - 离子色谱试剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (+)-薄荷酮
• 中文别名: (1S,4R)-对-薄荷烷-3-酮；(2R,5S)-2-异丙基-5-甲基环己酮
• 英文名称: l-menthone
• 英文别名: menthone；D-menthone；(2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-one
• CAS: 3391-87-5
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: NFLGAXVYCFJBMK-DTWKUNHWSA-N

物化性质

• 沸点：
  209-210 °C(lit.)
• 密度：
  0.893 g/mL at 20 °C(lit.)
• 闪点：
  72 °C
• 溶解度：
  氯仿（微溶）、乙醇（微溶）、甲醇（微溶）
• LogP：
  2.625 (est)
• 物理描述：
  colourless to pale yellowish liquid with a mint-like odour
• 颜色/状态：
  Colorless, oily, mobile liq
• 气味：
  Slight peppermint odor
• 味道：
  Bitter
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 折光率：
  INDEX OF REFRACTION: 1.4480-1.4520 @ 20 °C; SPECIFIC OPTICAL ROTATION: + OR - 2 DEG /DL-FORM/

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

酮类（例如香芹酮和薄荷酮）被还原成二级醇，然后这些二级醇作为葡萄糖苷酸被排出体外。薄荷酮通过不对称还原转化为新薄荷醇，再通过葡萄糖苷酸结合转化为薄荷基葡萄糖苷酸。

...KETONES (EG CARVONE & MENTHONE) ARE REDUCED TO SECONDARY ALCOHOLS WHICH ARE THEN EXCRETED AS GLUCURONIDES. MENTHONE, ASYMMETRIC REDUCTION /TO/ NEO-MENTHOL, GLUCURONIDE CONJUGATION /TO/ MENTHYL GLUCURONIDE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 非人类毒性摘录

向大鼠胃内给予3毫摩尔/公斤的孟烯酮，可以抑制肝脏S-3-羟基-3-甲基戊二酸辅酶A还原酶的活性50%。

ADMIN OF 3 MMOL/KG MENTHONE, INTRAGASTRICALLY TO RATS INHIBITED HEPATIC S-3-HYDROXY-3-METHYLGLUTARYL-COA REDUCTASE BY 50%.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

四种植物（两种薰衣草、薄荷和桉树）的精油及其主要成分，即芳樟醇、乙酸芳樟酯、茴香酮、薄荷酮、薄荷醇和桉树脑，在体外测试了对仓储食品中的害螨——长角扁谷盗的杀螨活性。进行了两种不同的程序来测试这些化合物的活性，一种是通过直接接触，另一种是通过吸入。在直接接触测试中，将每种未稀释物质的五种不同数量（6、2、1、0.5和0.25微升）涂抹在6厘米培养皿的内部表面，每个培养皿含有10只螨虫。通过吸入的活性测试使用了两种不同大小的培养皿：较小的6厘米培养皿，含有10只螨虫，上面覆盖有滤纸盘，并封闭在一个较大的9厘米培养皿中，其中含有6盎司2毫升的每种未稀释物质。在最高剂量下，两种薰衣草和薄荷的精油通过直接接触和吸入的方式杀死了100%的螨虫。桉树油活性最低。在精油成分中，薄荷醇显示出最高的活性，在直接接触时最低剂量（0.25微升）和吸入时6微升就能杀死100%的螨虫。然而，芳樟醇、茴香酮和薄荷酮也显示出良好的杀螨活性。与它所属的精油一样，桉树脑的活性最低。

Essential oils of four plants (two species of lavender, peppermint, and a eucalyptus) and some of their principal constituents, i.e., linalool, linalyl acetate, fenchone, menthone, menthol, and eucalyptol, were tested in vitro for their acaricidal activity against Tyrophagus longior, a mite species that is a pest in stored food. Two different procedures were carried out to test the activity of these compounds by direct contact and by inhalation. In the direct contact assays five different quantities of each undiluted substance (6, 2, 1, 0.5, and 0.25 ul) were spread on the internal surface of 6-cm petri dishes, each containing 10 mites. The activity by inhalation was tested using two petri dishes of different sizes: the smaller one (6 cm), containing 10 mites, was covered with a filter paper disk and enclosed in a bigger dish (9 cm) containing 6 oz 2 mul of each undiluted substance. At the highest doses, the essential oils of the two lavender species and of peppermint killed 100% of the mites, both by direct contact and by inhalation. Eucalyptus oil was the least active. Among the essential oil constituents, menthol showed the highest activity, killing 100% of the mites at the lowest dose (0.25 ul) by direct contact and at 6 ul by inhalation. However, linalool, fenchone, and menthone also showed good acaricidal activity. Eucalyptol, like the essential oil of which it is the principal constituent, had the lowest activity.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

Menthone是薄荷油的一个组成部分，它被口服给予10只雄性和10只雌性大鼠，剂量水平分别为0、200、400和800 mg/kg体重/天，持续28天。在第19天之后，最高剂量组的雌性大鼠的剂量降低到了400 mg/kg体重。对血浆的分析显示，肌酐含量随着剂量的增加而剂量依赖性地减少，碱性磷酸酶活性和胆红素随着剂量的增加而剂量依赖性地增加。肝脏和脾脏的相对重量增加了。在两个最高剂量组的动物的小脑白质中，组织病理学上观察到了类似囊肿的空间。在这项研究中，Menthone的无效应水平低于200 mg/kg体重/天。

Menthone, a component of peppermint oil, was given p.o. to groups of 10 male and 10 female rats at dose levels of 0, 200, 400 and 800 mg/kg bw/day, respectively, for 28 days. After 19 days the dose was reduced to 400 mg/kg bw in the female group receiving the highest dose. Analyses of plasma showed a dose-dependent decrease in creatinine content and a dose-dependent increase in alkaline phosphatase activity and bilirubin. The relative weights of liver and spleen were increased. Cyst-like spaces were seen histopathologically in the white matter of the cerebellum of the two highest dose groups. The no-effect level for menthone in this study was lower than 200 mg/kg bw/day.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

Menthone 对兔子的皮肤有轻微的刺激性，且在兔子身上急性皮肤毒性较低。在一项使用稀释溶液的志愿者研究中，没有发现致敏潜力的证据。在大鼠身上，Menthone 显示出中等到低度的急性口服毒性。在重复口服给药后，Menthone 导致大鼠肝脏、肾脏和脾脏的重量增加。在细菌沙门氏菌（Ames试验）中报告了致突变活性。

Menthone was a mild skin irritant and of low acute dermal toxicity in rabbits. No evidence of sensitizing potential was found in a volunteer study with a dilute solution. In rats, menthone demonstrated a moderate to low acute oral toxicity. On repeated oral administration, menthone produced increases in liver, kidney and spleen weights of rats. Mutagenic activity was reported in the bacterium Salmonella typhimurium (Ames test).

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 安全说明：
  S23,S24/25
• WGK Germany：
  3
• 海关编码：
  2914299000
• 储存条件：
  2-8°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : (+)-Menthone
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 3391-87-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : (1S,4R)-p-Menthan-3-one
(2R,5S)-2-Isopropyl-5-methylcyclohexanone
Formula : C10H18O
Molecular Weight : 154,25 g/mol
CAS-No. : 3391-87-5
EC-No. : 222-227-6
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapours, mist or gas. Remove all sources of ignition. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13). Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature: 2 - 8 °C
Store under inert gas.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: clear, liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 209 - 210 °C - lit.
boiling range
g) Flash point 72 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,893 g/cm3 at 20 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (+)-薄荷酮 在 葡萄糖 、 (-)-menthone:(+)-neomenthol reductase 、 glucose dehydrogenase from Pseudomonas sp 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以63%的产率得到(1Alpha,2Alpha,5β)-(+-)-5-甲基
  参考文献：
  名称：

  确定短链脱氢酶/还原酶中酮还原和“烯”还原之间的机制转换。

  摘要：

  薄荷精油生物合成途径的三种酶具有高度同源性，即酮还原酶（-）-薄荷酮：（-）-薄荷醇还原酶和（-）-薄荷酮：（+）-新薄荷醇还原酶，以及“烯”还原酶异哌酮还原酶. 我们在最后两个中发现了一种罕见的催化残基取代，并进行了比较晶体结构分析和残基交换诱变，以研究这是否决定了反应结果。结果是天然活性的完全丧失以及烯还原和酮还原之间的转换。这表明催化谷氨酸与酪氨酸残基在确定 α,β-不饱和烯烃还原结果中的重要性，因为底物占据不同的结合构象，也可能与两个残基的相对酸度有关。

  DOI：

  10.1002/anie.201603785
• 作为产物：
  描述：

  (+)-香茅醛 在 1.206wt% of ruthenium and 1.516wt% of copper supported metal organic framework 作用下， 10.0 ℃ 、300.01 kPa 条件下， 反应 15.0h， 以99.87%的产率得到
  参考文献：
  名称：

  一种由R-香茅醛制备L-薄荷酮的方法

  摘要：

  本发明公开了一种由R‑香茅醛制备L‑薄荷酮的方法，在Ru‑Cu‑MOF催化剂存在下将R‑香茅醛环化制备L‑薄荷酮，所述反应条件温和，反应对映选择性为90％～99.5％，转化率可达到95‑99.9％，薄荷酮ee值可达到90～99.9％。

  公开号：

  CN110903173B
• 作为试剂：
  描述：

  (E)-巴豆氯 、 4-苯基甲氧基-丁醛 在 magnesium 、 (+)-薄荷酮 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 以73%的产率得到(S,E)-1-(benzyloxy)oct-6-en-4-ol
  参考文献：
  名称：

  [5.5]-螺缩酮的固相合成

  摘要：

  已开发出一种在固体载体上高效且可靠地多步合成 251 种天然产物样 [5.5]-螺缩酮的方法。作为中心关键步骤，应用了对炔酮的双分子内杂迈克尔 (DIHMA) 反应。该序列允许在支架上引入许多取代基并允许立体化学的变化。[5.5]-带有额外酮的螺缩酮以高总产率获得。通过使用聚合物负载的硼氢化物还原酮和还原胺化、格氏反应和在溶液相中转化为肟衍生物，实现了进一步的多样化。

  DOI：

  10.1002/adsc.200800154

文献信息

• A New Method for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds by Using<i>N</i>-<i>t</i>-Butylbenzenesulfinimidoyl Chloride
  作者：Jun-ichi Matsuo、Daisuke Iida、Kazuya Tatani、Teruaki Mukaiyama

  DOI：10.1246/bcsj.75.223

  日期：2002.2

  Various primary and secondary alcohols were smoothly oxidized to the corresponding aldehydes and ketones by using a new oxidizing agent, N-t-butylbenzenesulfinimidoyl chloride (4a), in the coexistence of DBU or zinc oxide. The present oxidation proceeded under mild conditions via five-membered intramolecular proton-transfer of an alkyl arenesulfinimidate intermediate.

  在 DBU 或氧化锌的共存下，通过使用新的氧化剂 N-叔丁基苯亚磺酰亚胺酰氯 (4a)，将各种伯醇和仲醇顺利氧化成相应的醛和酮。本氧化反应在温和条件下通过烷基芳烃亚砜中间体的五元分子内质子转移进行。
• Highly chemoselective palladium-catalyzed conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds with silicon hydrides and zinc chloride cocatalyst
  作者：Ehud. Keinan、Noam. Greenspoon

  DOI：10.1021/ja00283a029

  日期：1986.11

  experiments and 'H NMR studies, a catalytic cycle is postulated in which the first step involves reversible coordination of the palladium complex to the electron-deficient olefin and oxidative addition of silicon hydride to form a hydridopalladium olefin complex. Migratory insertion of hydride into the coordinated olefin produces an intermediate palladium enolate which, via reductive elimination, collapses back

  由可溶性钯催化剂、氢化硅烷和氯化锌组成的三组分体系能够有效地共轭还原α、不饱和酮和醛。最佳条件组包括二苯基硅烷作为最有效的氢化物供体，任何可溶于 0 或 I1 氧化态的钯配合物，当它被膦配体稳定时，以及作为最佳路易斯酸助催化剂的 ZnCl。该反应对于范围广泛的不饱和酮和醛非常普遍，并且对于这些迈克尔受体具有高度选择性，因为在这些条件下α，-不饱和羧酸衍生物的还原非常缓慢。当双氘代二苯基硅烷用于还原不饱和酮时，氘在底物的受阻较少的面上立体选择性地引入，并在 8 位上以区域选择性的方式引入。相反，当在痕量 D2O 存在下进行还原时，氘掺入发生在 a 位。在掺入氘的实验和 1 H NMR 研究的基础上，假定催化循环，其中第一步涉及钯配合物与缺电子烯烃的可逆配位和氢化硅的氧化加成以形成氢化钯烯烃配合物。氢化物迁移插入配位的烯烃产生中间体烯醇钯，通过还原消除，它塌缩回 Pd(0) 络合物和甲硅烷基烯
• Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water
  作者：Tao Song、Zhiming Ma、Yong Yang

  DOI：10.1002/cctc.201801987

  日期：2019.2.20

  selectivity for hydrogenation of C=C in α,β‐unsaturated carbonyls under mild conditions. A broad set of α,β‐aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one‐pot cascade synthesis of saturated carbonyls was realized with high activity and

  在本文中，我们报道了由竹笋中的生物质衍生的碳负载的钴纳米颗粒与水中的分子氢在水中将α，β-不饱和羰基高度化学选择性氢化为饱和羰基，这是使用非均相非贵金属催化剂的首个原型据我们所知进行这种有机转型。最佳钴纳米催化剂CoO x@ NC-800在温和条件下表现出显着的活性，对α，β-不饱和羰基中的C = C进行氢化。广泛的α，β-芳族和脂族不饱和羰基被选择性还原为相应的饱和羰基，收率高达99％，并且对各种官能团具有良好的耐受性。同时，通过酮与醛的交叉羟醛缩合，然后进行选择性加氢，实现了一种新的，直接的，高活性和高选择性的饱和羰基单锅级联反应。更重要的是，这种单罐策略适用于从容易获得的起始原料合成卢瑞瑞林A（一种多功能的生物活性和药用分子）的权宜之计，这进一步突出了该催化剂的实用性。此外，
• Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes
  作者：Tayseer Mahdi、Douglas W. Stephan

  DOI：10.1002/anie.201503087

  日期：2015.7.13

  A series of ketones and aldehydes are reduced in toluene under H2 in the presence of 5 mol % B(C6F5)3 and either cyclodextrin or molecular sieves affording a facile metal‐free protocol for reduction to alcohols. Similar treatment of aryl ketones resulted in metal‐free deoxygenation yielding aromatic hydrocarbons.

  在H 2下，在5 mol％B（C 6 F 5）3的存在下，一系列甲苯中的酮和醛被还原，环糊精或分子筛提供了一种简便的无金属还原醇的方案。芳基酮的类似处理导致无金属脱氧，生成芳烃。
• PROCESS FOR THE PREPARATION OF NITRO COMPOUNDS AND METHOD FOR THE REMOVAL OF NITROGEN DIOXIDE
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1099684A1

  公开（公告）日：2001-05-16

  In the invented process for producing a nitro compound, an organic substrate and nitrogen dioxide are reacted in the presence of oxygen or are reacted in a molar ratio of nitrogen dioxide to the organic substrate of less than 1 to yield a corresponding nitro compound. The reaction may be performed in the presence of N-hydroxyphthalimide or other imide compounds. Such organic substrates include (a) aliphatic hydrocarbons, (b) alicyclic hydrocarbons, (c) non-aromatic heterocyclic compounds each having a carbon atom on a ring, which carbon atom is bonded to a hydrogen atom, (d) compounds each having a carbon-hydrogen bond at the adjacent position to an aromatic ring, and (e) compounds each having a carbon-hydrogen bond at the adjacent position to a carbonyl group. This process can efficiently nitrate an organic substrate even under relatively mild conditions.

  在制备硝基化合物的发明过程中，有机底物和二氧化氮在氧气存在下反应，或者在二氧化氮与有机底物的摩尔比小于1的情况下反应，以产生相应的硝基化合物。该反应可以在N-羟基邻苯二甲酰亚胺或其他亚酰胺化合物存在下进行。这样的有机底物包括(a) 脂肪烃，(b) 脂环烃，(c) 非芳香杂环化合物，每个环上的碳原子与氢原子相结合，(d) 每个化合物在芳香环旁边位置具有碳氢键，以及(e) 每个化合物在酮基旁边位置具有碳氢键。这个过程可以在相对温和的条件下有效地对有机底物进行硝化。

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