(1S,2S)-BOC-1,2-环己二胺 | 180683-64-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (1S,2S)-BOC-1,2-环己二胺
• 中文别名: (1S,2S)-叔丁氧羰基-1,2-环己二胺；(1S,2S)-1-(Boc-氨基)-2-氨基环己烷；(1S,2S)-反式-N-Boc-1,2-二氨基环己烷；(1S)-反式-N-Boc-1,2-二氨基环己烷；(1S,2S)-反式-N-BOC-1,2-二氨基环己烷
• 英文名称: tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate
• 英文别名: (1S,2S)-trans-N-Boc-1,2-cyclohexanediamine；tert-butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate；(1S,2S)-N-Boc-1,2-cyclohexanediamine；(1S,2S)-1-(N-t-butyloxycarbonylamino)-2-aminocyclohexane
• CAS: 180683-64-1
• 化学式: C₁₁H₂₂N₂O₂
• 分子量: 214.308
• InChiKey: AKVIZYGPJIWKOS-IUCAKERBSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  322.1±31.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2942000000
• 危险品运输编号：
  UN 3259 8/PG 3
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H314
• 储存条件：
  存储温度：0-10°C；应存放在惰性气体中；避免与空气接触和加热。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : (1S,2S)-trans-N-Boc-1,2-cyclohexanediamine
CAS-No. : 180683-64-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin corrosion (Category 1B)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Causes burns.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H314 Causes severe skin burns and eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R34 Causes burns.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : (1S)-trans-N-Boc-1,2-diaminocyclohexane
Formula : C11H22N2O2
Molecular Weight : 214,3 g/mol
Component Concentration
(1S,2S)-trans-N-Boc-1,2-cyclohexanediamine
CAS-No. 180683-64-1 -

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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
Take off contaminated clothing and shoes immediately. Wash off with soap and plenty of water. Consult a
physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
Cough, Shortness of breath, Headache, Nausea, Vomiting
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, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. 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 formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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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
Face shield and safety glasses 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
Complete suit protecting against chemicals, 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 particle
respirator type N100 (US) or type P3 (EN 143) 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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: crystalline
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 117 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation 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 completely miscible
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition 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
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Air
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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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 sensitization
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
Potential health effects
Inhalation May be harmful if inhaled. Material is extremely destructive to the tissue of
the mucous membranes and upper respiratory tract.
Ingestion May be harmful if swallowed. Causes burns.
Skin May be harmful if absorbed through skin. Causes skin burns.
Eyes Causes eye burns.
Signs and Symptoms of Exposure
Cough, Shortness of breath, Headache, Nausea, Vomiting
Additional Information
RTECS: Not available

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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
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 3259 IMDG: 3259 IATA: 3259
UN proper shipping name
ADR/RID: AMINES, SOLID, CORROSIVE, N.O.S. ((1S,2S)-trans-N-Boc-1,2-cyclohexanediamine)
IMDG: AMINES, SOLID, CORROSIVE, N.O.S. ((1S,2S)-trans-N-Boc-1,2-cyclohexanediamine)
IATA: Amines, solid, corrosive, n.o.s. ((1S,2S)-trans-N-Boc-1,2-cyclohexanediamine)
Transport hazard class(es)
ADR/RID: 8 IMDG: 8 IATA: 8
Packaging group
ADR/RID: III IMDG: III IATA: III
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

制备方法与用途

(1S,2S)-BOC-1,2-环己二胺是一种用于医药中间体的胺类有机化合物。

反应信息

• 作为反应物：
  描述：

  (1S,2S)-BOC-1,2-环己二胺 在 sodium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 benzyl N-[(1S,2S)-2-aminocyclohexyl]carbamate
  参考文献：
  名称：

  在氨基甲酸酯单保护的 1,2-二胺催化的马来酰亚胺中加入醛，合成琥珀酰亚胺的溶剂诱导的对映选择性逆转

  摘要：

  作者感谢西班牙经济与竞争部长 (MEC)（项目编号 CTQ2011-24151）、欧洲基金会（FEDER）、COST 行动 CM0905“有机催化”、FP7 玛丽居里行动的财政支持欧盟委员会通过 ITN ECHONET 网络 (FP7-MCITN-2012-316379)、阿利坎特大学和巴斯克大学。

  DOI：

  10.1002/ejoc.201403415
• 作为产物：
  描述：

  (1S,2S)-tert-butyl-N-[2-(diallylamino)cyclohexyl]carbamate 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 作用下， 以 甲苯 为溶剂， 以81%的产率得到(1S,2S)-BOC-1,2-环己二胺
  参考文献：
  名称：

  一种制备旋光的伯-叔反式-环烷烃1,2-二胺的有效化学酶方法

  摘要：

  光学活性的反式- ñ -Boc-环戊烷和环己烷-1,2-二胺（7 - ），通过从相应的（±）一个化学酶促方法制备的反式- Ñ，Ñ -diallylcycloalkane -1,2-二胺。这些单氨基甲酸酯7（ee = 99％）被用作合成不同邻位伯-叔二胺的原料。因此，通过包括芳香醛的还原胺化通过简单的三步骤顺序的手段7，N-甲基化，最后，Boc基团的裂解，几个反式- ñ - （芳甲基） - ñ高产率地获得了-甲基环戊烷-和环己烷-1,2-二胺。

  DOI：

  10.1016/j.tet.2009.07.035
• 作为试剂：
  描述：

  1-(4-甲氧苯基)-2-硝基乙烯 、 丙酮 在 藜芦酸 、 (1R,2R)-反式-N-Boc-1,2-二氨基环己烷 、 (1S,2S)-BOC-1,2-环己二胺 作用下， 以 氯仿 为溶剂， 生成 (±)-4-(4-methoxyphenyl)-5-nitropentan-2-one
  参考文献：
  名称：

  Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines

  摘要：

  Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched beta-substituted gamma-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.07.011

文献信息

• Primary Amine–2-Aminopyrimidine Chiral Organocatalysts for the Enantioselective Conjugate Addition of Branched Aldehydes to Maleimides
  作者：Carmen Nájera、Enrique Gómez-Bengoa、Pascuala Vízcaíno-Milla、José Sansano、Béla Fiser

  DOI：10.1055/s-0034-1380718

  日期：——

  corresponding succinimides in good yields and enantioselectivities. DFT calculations support the stereochemical results and the role played by the solvents. Chiral primary amines containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a pyrimidin-2-yl unit are synthesized and used as general organocatalysts for the Michael reaction of α-branched aldehydes to maleimides. The reaction

  摘要 合成含有（R，R）-和（S，S）-反式-环己烷-1,2-二胺骨架和嘧啶-2-基单元的手性伯胺，并将其用作α-的迈克尔反应的一般有机催化剂支链醛成马来酰亚胺。该反应在10℃下在N，N-二甲基甲酰胺水溶液中以10mol％的有机催化剂负载量和己二酸作为助催化剂进行，以良好的产率和对映选择性提供了相应的琥珀酰亚胺。DFT计算支持立体化学结果和溶剂的作用。 合成含有（R，R）-和（S，S）-反式-环己烷-1,2-二胺骨架和嘧啶-2-基单元的手性伯胺，并将其用作α-的迈克尔反应的一般有机催化剂支链醛成马来酰亚胺。该反应在10℃下在N，N-二甲基甲酰胺水溶液中以10mol％的有机催化剂负载量和己二酸作为助催化剂进行，以良好的产率和对映选择性提供了相应的琥珀酰亚胺。DFT计算支持立体化学结果和溶剂的作用。
• Direct Asymmetric Aldol Reaction Catalyzed by C2-Symmetrical Chiral Primary Amine Organocatalysts
  作者：Gong-Jian Zhu、Chao-Shan Da、Ya-Ning Jia、Xiao Ma、Lei Yi

  DOI：10.2174/157017810790533904

  日期：2010.1.1

  C-2-symmetrical chiral primary amines were synthesized from chiral BINOL and diamines. Then their catalytic activities in the asymmetric aldol reactions were evaluated, and the result indicated that 1c was the optimal organocatalyst. The reaction of a variety of aromatic aldehydes with aliphatic ketones, catalyzed by 20 mol % 1c in the addition of benzoic acid in carbon tetrachloride, afforded the aldol products

  从手性 BINOL 和二胺合成了三种新型 C-2 对称手性伯胺。然后评估了它们在不对称醛醇反应中的催化活性，结果表明1c是最佳的有机催化剂。在四氯化碳中加入苯甲酸，在 20 mol % 1c 的催化下，多种芳香醛与脂肪族酮反应得到高产率（高达 92%）和良好的对映选择性（高达 71%）的醛醇产物.
• Pyrimidine-Derived Prolinamides as Recoverable Bifunctional Organocatalysts for Enantioselective Inter- and Intramolecular Aldol Reactions under Solvent-Free Conditions
  作者：Pascuala Vizcaíno-Milla、José M. Sansano、Carmen Nájera、Béla Fiser、Enrique Gómez-Bengoa

  DOI：10.1002/ejoc.201500007

  日期：2015.4

  Chiral L-prolinamides 2 containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are synthesized and used as general organocatalysts for intermolecular and intramolecular aldol reactions with 1,6-hexanedioic acid as a co-catalyst under solvent-free conditions. The intermolecular reaction between ketone–aldehyde and aldehyde–aldehyde must be performed under wet

  合成了含有 (R,R)- 和 (S,S)-反式-环己烷-1,2-二胺支架和 2-嘧啶基单元的手性 L-脯氨酰胺 2 并用作分子间和分子内羟醛反应的通用有机催化剂1,6-己二酸作为无溶剂条件下的助催化剂。酮-醛和醛-醛之间的分子间反应必须在湿条件下使用催化剂 (S,S)-2b 在 10 °C 下进行，这提供了具有高区域选择性、非对映选择性和对映选择性的抗醛醇。对于 Hajos-Parrish-Eder-Sauer-Wiechert 反应，催化剂 2 的两种非对映异构体在室温下无水条件下给出相似的结果，得到相应的 Wieland-Miescher 酮和衍生物。两种类型的反应均按比例放大至 1 g，有机催化剂通过萃取后处理回收并重复使用，而没有任何明显的活性损失。DFT 计算通过提供催化剂 2a 和 2b 发生的 H 键网络的计算比较来支持分子间过程的立体化学结果和有机催化剂发挥的双功能作用。
• Squaramide-Linked Chloramphenicol Base Hybrid Catalysts for the Asymmetric Michael Addition of 2,3-Dihydrobenzofuran-2-carboxylates to Nitroolefins
  作者：Linjie Yan、Guanxin Huang、Haifeng Wang、Fangjun Xiong、Haihui Peng、Fener Chen

  DOI：10.1002/ejoc.201701485

  日期：2018.1.10

  of hybrid catalysts incorporating chloramphenicol base with another chiral scaffold using a squaramide linker have been developed and successfully applied in Michael addition of 2,3-dihydrobenzofuran-2-carboxylates to nitroolefins. The controlling experiments suggested that the hybrid catalysts were more reactive than non-hybridized bifunctional catalysts and the matching of chiralities between two

  已开发出一系列新型混合催化剂，将氯霉素碱与另一种使用方酸酰胺接头的手性支架相结合，并成功应用于 2,3-二氢苯并呋喃-2-羧酸盐与硝基烯烃的迈克尔加成反应。对照实验表明，杂化催化剂比非杂化双功能催化剂更具反应性，两个支架之间手性的匹配对于高反应性和立体选择性至关重要。事实证明，这种混合有机催化剂适用于各种底物。在 0.5 mol% 催化剂负载量的情况下，以高产率（高达 98%）获得了一系列带有季-叔立体中心的 2,3-二氢苯并呋喃-2-羧酸酯衍生物，并具有出色的对映选择性（高达 99% ee）和中等非对映选择性（高达 8/92 dr）。
• Synthesis of Novel Macrocyclic Tetraamides
  作者：Barun Mehta、Dandela Rambabu、Guttikonda Raja、ASG. Prasad、Jim-Min Fang、Mandava Rao

  DOI：10.2174/1570180811666140116215724

  日期：2014.5.31

  A simple and facile route has been described for the synthesis of macrocyclic tetraamides. This method is applicable for the preparation of a variety of macrocyclic tetraamides of various heteroatom substitutions.

  提出了一种简单易行的合成大环四酰胺的途径。该方法适用于制备多种具有不同杂原子取代基的大环四酰胺。