(R)-(-)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalene-2-one | 63975-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(-)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalene-2-one
• 英文别名: (R)-(-)-4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone；(R)-(-)-10-Methyl-1(9)-octal-2-one；(4aR)-4a-methyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 63975-59-7
• 化学式: C₁₁H₁₆O
• mdl: MFCD00009959
• 分子量: 164.247
• InChiKey: OHERZLWVBJCXOF-LLVKDONJSA-N

物化性质

• 沸点：
  155 °C17 mm Hg(lit.)
• 比旋光度：
  -215～-230°
• 密度：
  1.018 g/mL at 20 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  在常温常压下保持稳定，应远离氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 海关编码：
  2914299000
• 储存条件：
  存放在密封容器内，并放置在阴凉、干燥的地方。

SDS

Name:	(R)-(-)-10-Methyl-1(9)-octal-2-one 98.5% Material Safety Data Sheet
Synonym:	(R)-(-)-4,4a,5,6,7,8-Hexahydro-4a-methyl-2(3H)-naphthalenone
CAS:	63975-59-7

Section 1 - Chemical Product MSDS Name:(R)-(-)-10-Methyl-1(9)-octal-2-one 98.5% Material Safety Data Sheet
Synonym:(R)-(-)-4,4a,5,6,7,8-Hexahydro-4a-methyl-2(3H)-naphthalenone

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
63975-59-7	(R)-(-)-10-Methyl-1(9)-octal-2-one	98.5	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 63975-59-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 85-86 deg C @ 0.2 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.010 g/cm3
Molecular Formula: C11H16O
Molecular Weight: 164.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 63975-59-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-(-)-10-Methyl-1(9)-octal-2-one - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 63975-59-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 63975-59-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 63975-59-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-(-)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalene-2-one 在 Fe³-montmorillonite 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以97%的产率得到4-(3-pyridylmethyl)benzaldehyde diethyl acetal
  参考文献：
  名称：

  Efficient and regioselective cyanosilylation of cyclohex-2-enone and other unsaturated ketones over solid acid and base catalysts

  摘要：

  氰基三甲基硅烷与α,β-不饱和酮反应，在强酸性蒙脱石和强碱性氧化钙或氧化镁的存在下，分别生成1,4-和1,2-加成产物，具有区域选择性。

  DOI：

  10.1039/c39910001035
• 作为产物：
  描述：

  (1R.E)-N-(2-methylcyclohexylidene)-1-phenylethanamine 在 甲醇 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 74.0h， 生成 (R)-(-)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalene-2-one
  参考文献：
  名称：

  通过手性亚胺的迈克尔型烷基化对映选择性合成季碳中心

  摘要：

  制备环烷酮手性二取代物和 2,2 对烷基化亚胺手性环烷酮单取代物

  DOI：

  10.1021/ja00287a061

文献信息

• Asymmetric Michael-type alkylation of chiral imines. Enantioselective syntheses of (−)-geosmin and two other related natural terpenes, as well as enant-(+)-geosmin
  作者：Gilbert Revial

  DOI：10.1016/s0040-4039(00)99338-9

  日期：1989.1

  Natural (−)-geosmin 11, (+)-octalone 14 (from Vetiveria zizanioides), and (+)-octalin 15 (from Bazzania fauriana and B. angustifolia) have been prepared in high chemical and enantiomeric yields via the asymmetric process involving Michael-type alkylation of chiral imines 6 and 12. Enant-(+)-geosmin has been also synthesized by the same procedure.

  已通过不对称过程制备了高化学收率和对映体收率的天然（-）-地臭素11，（+）-八氢萘酸14（来自Vetiveria zizanioides）和（+）-八氢萘酸15（来自Bazzania fauriana和B. angustifolia）。手性亚胺6和12的迈克尔型烷基化。还通过相同的方法合成了对映体-（+）-地奥斯明。
• Sustainable Epoxidation of Electron-Poor Olefins with Hydrogen Peroxide in Ionic Liquids and Recovery of the Products with Supercritical CO2
  作者：Olga Bortolini、Sandro Campestrini、Valeria Conte、Giancarlo Fantin、Marco Fogagnolo、Silvia Maietti

  DOI：10.1002/ejoc.200300442

  日期：2003.12

  An efficient procedure is described for the epoxidation of electron-deficient olefins, in particular Vitamin K-3 and analogues, with aqueous basic solutions of hydrogen peroxide in different ambient temperature ionic liquids (ILs) [bmim(+)][X-] [bmim(+)] = 1-butyl-3-methylimidazolium; [X-] = [BF4-], [CF3SO3-], [PF6-] [N(CF3SO2)(2)(-)]}. Various factors affecting epoxide yield (in the range 80-99%)

  描述了在不同环境温度的离子液体 (IL) [bmim(+)][X-] 中使用过氧化氢碱性水溶液环氧化缺电子烯烃，特别是维生素 K-3 和类似物的有效程序[bmim(+)] = 1-丁基-3-甲基咪唑鎓；[X-] = [BF4-], [CF3SO3-], [PF6-] [N(CF3SO2)(2)(-)]}。已经检查了影响环氧化物产率（80-99%）、反应速率和再现性的各种因素。用超临界 CO2 从反应介质中几乎定量地提取环氧化物。然后回收离子液体并在随后的循环中重新使用。(C) Wiley-VCH Verlag GmbH & Co.KGaA, 69451 Weinheim, Germany, 2003。
• Solid Acid and Base-Catalyzed Cyanosilylation of Carbonyl Compounds with Cyanotrimethylsilane
  作者：Katsumi Higuchi、Makoto Onaka、Yusuke Izumi

  DOI：10.1246/bcsj.66.2016

  日期：1993.7

  reaction of Me3SiCN with aldehydes and ketones to afford the corresponding 2-(trimethylsiloxy)alkanenitriles in good yields. The reactions of dimethyl acetals with Me3SiCN in the presence of solid acids afforded 2-methoxyalkanenitriles. In cyanosilylations of α,β-unsaturated ketones two kinds of adducts were produced selectively, depending on the use of a solid acid or a solid base: 1,4-Adducts (trimethylsilyl

  研究了利用无机固体酸和碱促进氰基三甲基硅烷 (Me3SiCN) 与羰基化合物反应的新尝试。强酸性固体，如 Sn4+ 离子交换蒙脱石 (Sn-Mont) 和 Fe3+ 离子交换蒙脱石 (Fe-Mont)，以及碱性固体，如氟化钙 (CaF2)、羟基磷灰石 (HAp)、氧化钙 ( CaO)和氧化镁 (MgO) 催化 Me3SiCN 与醛和酮的反应，以良好的收率得到相应的 2-（三甲基甲硅烷氧基）烷腈。在固体酸存在下，二甲基缩醛与 Me3SiCN 反应得到 2-甲氧基链烷腈。在 α,β-不饱和酮的氰基硅烷化反应中，根据使用的固体酸或固体碱有选择地产生两种加合物：1、
• Beyond Butadiene II:  Thermal Isomerization of the [2 + 2] Photodimer of an <i>a</i><i>ll-trans</i>-Tetraene, (<i>R</i>)-4,4a<i>β</i>,5,6,10,10a-Hexahydro-10a<i>β</i>-methyl-2(3<i>H</i>)-methyleneanthracene, to a 16-Membered [8 + 8] Cycle
  作者：W. von E. Doering、Jianing He、Liming Shao

  DOI：10.1021/ja011135n

  日期：2001.9.1

  Enthalpies of stabilization of polyenyl radicals of increasing order previously obtained by thermal geometrical isomerization are applied to the ethylene-cyclobutane paradigm. Progressively lower enthalpies of activation for thermal cyclodimerization and its reverse, cycloreversion, are predicted and realized. Photochemical dimerization at -75 degrees C of the optically pure tetraene of the title (1) at the

  先前通过热几何异构化获得的递增顺序的多烯基的稳定焓被应用于乙烯-环丁烷范例。预测并实现了逐渐降低的热环二聚化及其逆向、环化反应的活化焓。标题 (1) 的光学纯四烯在半环双键处在 -75 摄氏度的光化学二聚作用主要产生三种允许的环丁烷 (4) 中的一种 (4-axx)，暂定构型抗exo,exo 已分配。三种环丁烷 (4) 之间的平衡、较慢的重排为热力学相当稳定的 [8 + 8] 环十六碳六烯 (16)，以及在 -42.3 和 -8.2 摄氏度之间的动力学研究。二聚体 16 到单体 1 的 Cycloreversion 发生在 60.4-86.6 摄氏度的范围内（DeltaH = 31.7 kcal mol(-1)，DeltaS = +10.8 cal mol(-1) K(-1)）。在这些 1,2-二己三烯基环丁烷中，立体突变率和环回复率之比明显高于两个稳定性较差的先前公开的实施例。考虑了 Doubleday
• The Cyclohexadienyl Radical in the Thermal Syn−Anti Isomerization of Two Crossed Pentaenes of the Type of Bis-Homofulvalene
  作者：W. von E. Doering、Ludmila Birladeanu、Keshab Sarma、Li-Sming Shao

  DOI：10.1021/ja953416z

  日期：1996.1.1

  elucidation of the dependence of enthalpy of stabilization on configuration among the pentadienyl radicals, a designer pentaene of the (Z,Z) type, (R,R)-5,5‘,6,6‘,7,7‘,8,8‘-octahydro-4a,4a‘-dimethyl-2,2‘-bi-4a(H)-naphthylidene, has been prepared and subjected to a kinetic study of cis, trans isomerization about its central double bond. The resulting activation parameters and those of a more complicated

  为了进一步阐明稳定焓对戊二烯基自由基构型的依赖性，设计了 (Z,Z) 型 (R,R)-5,5',6,6',7,7' 的戊烯,8,8'-octahydro-4a,4a'-二甲基-2,2'-bi-4a(H)-naphthylidene，已制备并对其中心双键进行顺反异构化的动力学研究。所得的活化参数和更复杂的例子 3,3'-bicholesta-1,4-二亚苯基的活化参数基本相同，它们的平均值为 ΔH⧧ = 36.8 kcal/mol 和 ΔS⧧ = +1.8 eu。这种活化焓显着高于 (E,E) 和 (E,Z) 构型的戊烯。双高富瓦烯型共面交叉共轭体系中的共轭相互作用尚未通过理论计算进行实验评估或估计，环己二烯基的稳定焓目前还不能确定。如果将共轭相互作用等同于四个 Kistiako ......