[3aS-(3aα,5aβ,6aβ,6bα)]-4-溴-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烷并[e]-1,3-苯并二茂 | 130669-74-8

• 物质功能分类: 化学试剂 - 有机试剂 - 环氧化物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [3aS-(3aα,5aβ,6aβ,6bα)]-4-溴-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烷并[e]-1,3-苯并二茂
• 中文别名: [3aS-(3aAlpha,5aβ,6aβ,6bAlpha)]-4-溴-3a,5a,6a,6b-四羟基-2,2-二甲基oxireno[e]-苯并间二氧杂环戊烯
• 英文名称: (1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol
• 英文别名: (1R,2R,3S,4S)-5-bromo-1,2-epoxy-3,4-isopropylidenedioxy-5-cyclohexene；(3aS,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2',3':3,4]benzo[1,2-d][1,3]dioxole；(3aS,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2’,3’,3,4]benzo[1,2-d][1,3]dioxole；(3As,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole
• CAS: 130669-74-8
• 化学式: C₉H₁₁BrO₃
• 分子量: 247.089
• InChiKey: IJFOOAYHPAECGI-WCTZXXKLSA-N

物化性质

• 熔点：
  76-79 °C(lit.)
• 沸点：
  293.8±40.0 °C(Predicted)
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: [3aS-(3aα,5aβ,6aβ,6bα)]-4-Bromo-3a,5a,6a,6b-
Product name
tetrahydro-2,2-dimethyloxireno[e]-1,3-benzodioxole
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. : 130669-74-8

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
Formula : C9H11BrO3
Molecular Weight : 247,09 g/mol
CAS-No. : 130669-74-8
No components need to be disclosed according to the applicable regulations.

---

SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
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
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Hydrogen bromide gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

---

SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
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.
Recommended storage temperature: -20 °C
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

---

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

---

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 76 - 79 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
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 no data available
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

---

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
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

---

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

---

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

---

SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

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

---

SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  [3aS-(3aα,5aβ,6aβ,6bα)]-4-溴-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烷并[e]-1,3-苯并二茂 在 氢氧化钾 、 偶氮二异丁腈 、 硫酸 、 三正丁基氢锡 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 Inositol
  参考文献：
  名称：

  Inositol synthesis: concise preparation of l-chiro-inositol and muco-inositol from a common intermediate

  摘要：

  Fully stereoselective large-scale syntheses have been attained for L-chiro-inositol (2) and muco-inositol (3) by means of controlled peripheral oxygenation of cyclohexadiene diol 1. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00182-7
• 作为产物：
  描述：

  (1R,2S,5R,6S)-3-bromo-6-iodo-1,2-O-isopropylidenecyclohex-3-ene-1,2,5-triol 在 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 [3aS-(3aα,5aβ,6aβ,6bα)]-4-溴-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烷并[e]-1,3-苯并二茂
  参考文献：
  名称：

  Selectivity in the halohydroxylation of cyclohexadienediols

  摘要：

  The halohydroxylation of a number of cyclohexadienediol derivatives has been investigated. The selectivity of the reaction as a function of the type of substituent on the diene, protecting group of the diol functionality, halonium donor, medium polarity, and temperature is described. Best selectivity is obtained for iodohydrin formation. The course of the reaction for these dienic systems is heavily dependent on steric factors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.109

文献信息

• The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents
  作者：Ehab S. Taher、Prue Guest、Amanda Benton、Xinghua Ma、Martin G. Banwell、Anthony C. Willis、Tobias Seiser、Trevor W. Newton、Johannes Hutzler

  DOI：10.1021/acs.joc.6b02372

  日期：2017.1.6

  A series of 28 analogues of the phytotoxic geranylcyclohexentriol (−)-phomentrioloxin A (1) has been synthesized through cross-couplings of various enantiomerically pure haloconduritols or certain deoxygenated derivatives with either terminal alkynes or borylated alkenes. Some of these analogues display modest herbicidal activities, and physiological profiling studies suggest that analogue 4 inhibits

  一系列的植物毒性geranylcyclohexentriol 28个类似物（ - ） - phomentrioloxin A（1）已经通过各种对映体纯或haloconduritols某些脱氧衍生物与任一末端炔烃或烯烃borylated的交叉偶联合成。这些类似物中的一些表现出适度的除草活性，并且生理学概况研究表明，类似物4在体外抑制分离的类囊体中的光系统II。
• Antifungal Activity of a Library of Cyclitols and Related Compounds
  作者：Ana Bellomo、Ana Bertucci、Victoria Sovera、Gonzalo Carrau、Marcela Raimondi、Susana Zacchino、Helio Stefani、David Gonzalez

  DOI：10.2174/15701808113109990036

  日期：2013.11

  Chemistry, University of Pennsylvania, United States. Depto. de Quimica Organica, Facultad. de Quimica, Universidad de la Republica, UdelaR, Montevideo, Uruguay. Farmacognosia, Facultad de Ciencias Bioquimicas y Farmaceuticas, Universidad Nacional de Rosario, Rosario, Argentina. Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas, Universidade de Sao Paulo, Sao Paulo, SP, Brazil.

  隶属机构：Roy 和 Diana Vagelos 实验室，宾夕法尼亚大学/默克高通量实验实验室，化学系，美国宾夕法尼亚大学。部。de Quimica Organica, Facultad。de Quimica, Universidad de la Republica, UdelaR, 蒙得维的亚, 乌拉圭。Farmacognosia, Facultad de Ciencias Bioquimicas y Farmaceutica, Universidad Nacional de Rosario, Rosario, Argentina。Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas，圣保罗大学，圣保罗，SP，巴西。
• The Synthesis of Certain Derivatives and Analogues of (−)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase
  作者：Joshua N. Buckler、Ehab S. Taher、Nicolas J. Fraser、Anthony C. Willis、Paul D. Carr、Colin J. Jackson、Martin G. Banwell

  DOI：10.1021/acs.joc.7b01062

  日期：2017.8.4

  Syntheses of certain di- and mono-oxygenated derivatives (e.g., 2 and 3, respectively) and analogues (e.g., 4, a D-ring monoseco-analogue of 2) of both the (−)- and (+)-enantiomeric forms of the alkaloid galanthamine [(−)-1] are reported. All have been assessed for their capacities to inhibit acetylcholine esterase but, in contrast to the predictions from docking studies, none bind strongly to this

  （-）-和（+）-对映体形式的某些双加氧和单加氧衍生物（例如分别为2和3）和类似物（例如4，D环的2的单环类似物）的合成报告了生物碱加兰他敏[（-）- 1 ]的含量。已经评估了它们全部抑制乙酰胆碱酯酶的能力，但是与对接研究的预测相反，没有一个与该酶强烈结合。
• Chemoenzymatic Total Synthesis and Reassignment of the Absolute Configuration of Ribisin C
  作者：Ping Lan、Martin G. Banwell、Jas S. Ward、Anthony C. Willis

  DOI：10.1021/ol403220t

  日期：2014.1.3

  enzymatically derived cis-1,2-dihydrocatechol 5 has been converted, by two related pathways, into compounds 3 and ent-3. As a result, it has been determined that the true structure of the natural product ribisin C is represented by ent-3.

  对映体纯和酶促衍生的顺式-1,2-二氢邻苯二酚5已通过两种相关途径转化为化合物3和ent - 3。结果，已经确定天然产物核糖蛋白C的真实结构由ent - 3表示。
• New, Homochiral Synthons Obtained through Simple Manipulations of Enzymatically Derived 3-Halo-cis-1,2-dihydrocatechols
  作者：Lorenzo V. White、Ping Lan、Brett D. Schwartz、Anthony C. Willis、Martin G. Banwell

  DOI：10.1071/ch15061

  日期：——

  The bromoepoxide 5a, which is obtained from the homochiral and enzymatically derived cis-1,2-dihydrocatechol 1a, is readily and efficiently transformed into either isomer 8a or the corresponding methoxymethyl-ether 2a. Though both of these products can be fully characterized, they are somewhat unstable, with the former being converted into the crystalline enone 3a on standing and the latter readily participating in a Diels–Alder cycloaddition reaction with the potent dienophile N-phenyl-1,2,4-triazoline-3,5-dione to give adduct 7a. The single-crystal X-ray structures of compounds 3a and 7a are reported. Using the related chemistry the chloro-analogue, 3b, of enone 3a can be obtained.

  溴环氧化物 5a 是由同手性的顺式-1,2-二氢邻苯二酚 1a 酶解而得，它很容易并高效地转化为异构体 8a 或相应的甲氧基甲基醚 2a。虽然这两种产物都能完全定性，但它们都有些不稳定，前者在静置后会转化为结晶烯酮 3a，后者则很容易与强效亲二烯剂 N-苯基-1,2,4-三唑啉-3,5-二酮发生 Diels-Alder 环加成反应，生成加合物 7a。报告了化合物 3a 和 7a 的单晶 X 射线结构。利用相关的化学方法可以得到烯酮 3a 的氯代对映体 3b。