S-Α,Α-双(3,5-二甲基苯基)脯氨醇 | 131180-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: S-Α,Α-双(3,5-二甲基苯基)脯氨醇
• 中文别名: (S)-α,α-双(3,5-二甲苯基)-2-吡咯烷甲醇；S-alpha,alpha-双(3,5-二甲基苯基)脯氨醇；(S)-(-)-2-[双(3,5-二甲苯基)羟甲基]吡咯烷
• 英文名称: bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol
• 英文别名: (S)-(-)-α,α-bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol；(S)-bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol；bis(3,5-dimethylphenyl)-[(2S)-pyrrolidin-2-yl]methanol
• CAS: 131180-63-7
• 化学式: C₂₁H₂₇NO
• 分子量: 309.451
• InChiKey: MXIOBZPVLNQGIU-FQEVSTJZSA-N

物化性质

• 熔点：
  98-101 °C
• 沸点：
  488.2±35.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn,N
• 安全说明：
  S60
• 危险类别码：
  R22
• WGK Germany：
  3
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 储存条件：
  储存温度应控制在2-8°C，需避光并保持干燥。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: (S)-α,α-Bis(3,5-dimethylphenyl)-2-
Product name
pyrrolidinemethanol
CAS-No. : 131180-63-7
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]
Acute toxicity, Oral (Category 4)
Acute aquatic toxicity (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic
environment.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H400 Very toxic to aquatic life.
Precautionary statement(s)
P273 Avoid release to the environment.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in
the aquatic environment.
S-phrase(s)
S60 This material and its container must be disposed of as hazardous waste.
S61 Avoid release to the environment. Refer to special instructions/ Safety
data sheets.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: (S)-(−)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine
Synonyms
Formula : C21H27NO
Molecular Weight : 309,45 g/mol
Component Concentration
(S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol
CAS-No. 131180-63-7 -

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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
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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 contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
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: 2 - 8 °C
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
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
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
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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: powder
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: 98 - 101 °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 no data available
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
no data available
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. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
Very toxic to aquatic life.

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

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. ((S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol)
TOXIC SOLID, ORGANIC, N.O.S. ((S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol)
IMDG:
Toxic solid, organic, n.o.s. ((S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol)
IATA:
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
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
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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  S-Α,Α-双(3,5-二甲基苯基)脯氨醇 以99%的产率得到
  参考文献：
  名称：

  MATHRE, DAVID J.;JONES, TODD K.;XAVIER, LYNDON C.;BLACKLOCK, THOMAS J.;RE+, J. ORG. CHEM., 56,(1991) N, C. 751-762

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲基溴苯 在 palladium dihydroxide 氢气 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 S-Α,Α-双(3,5-二甲基苯基)脯氨醇
  参考文献：
  名称：

  环己烯氧化物和CO2与二聚锌配合物的不对称交替共聚

  摘要：

  二聚锌配合物 2a [ = Et(2)Zn(2)(1a)(2)] 已通过 Et(2)Zn 和 (S)-二苯基(吡咯烷-2-基)甲醇 (1a- H）。X 射线晶体学显示，醇盐配体取代了 Et(2)Zn 的两个乙基基团之一，并通过 Zn-N 配位键形成了五元螯合环。两个锌中心由氧原子桥接以形成 Zn(2)O(2) 四元环与锌中心上的两个乙基组之间的同步关系。二聚锌配合物 2a 是环己烯氧化物和 CO(2) 不对称交替共聚的活性催化剂。所得共聚物的 MALDI-TOF 质谱表明共聚反应是通过将 CO(2) 插入 Zn-醇盐而引发的，得到 [(S)-二苯基 (pyrroridin-2-ly) 甲氧基]-[C(= O)O-(1,2-亚环己基)-O](n)-H(共聚物I)，包括手性配体 1a 作为起始基团。配合物 3a-OEt ( = EtZn(1a)(2)ZnOEt)，其中乙氧基取代了 2a 中的两个乙基之一，也聚合了具有比

  DOI：

  10.1021/ja028666b
• 作为试剂：
  描述：

  (S)-ethyl 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetate 在 盐酸 、 lithium aluminium tetrahydride 、 草酰氯 、 2-甲基苯硼酸 、 水 、 potassium carbonate 、 S-Α,Α-双(3,5-二甲基苯基)脯氨醇 、 双三氟甲烷磺酰亚胺 、 二甲基亚砜 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 34.0h， 生成 (S)-N-propargyl-2-hydroxy-3-((S)-2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)propionamide
  参考文献：
  名称：

  一类褪黑激素(MT1-MT2)受体激动剂及其 制备方法与用途

  摘要：

  本发明公开了一类褪黑激素(MT1‑MT2)受体激动剂，是通式(I)化合物或其光学异构体，通式(I)中：n选自1‑5；A选自CH2，氧或NH；D选自CH2或氧；选自(双键)或‑(单键)；B选自R选自氢，C1‑C6饱和直链烷基或C3‑C6饱和支链烷基或C3‑C6环烷基或C3‑C6不饱和直链或支链烷基；R1选自氢或氟；R2选自氢、羟基、巯基、氨基、卤素或C1‑C6直链或支链烷基；R3选自C1‑C6直链烷基或C3‑C6支链烷基；所述烷基是未取代的或被一至三个独立选自下组的基团所取代：卤素，OH，NH2，或CN。此外，本发明还公开了该化合物的制备方法及其在制备治疗与褪黑激素MT1‑MT2受体相关疾病的药物中的应用。

  公开号：

  CN104109143B

文献信息

• Highly Enantioselective Hydrosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion
  作者：Byung Chul Kang、Sung Ho Shin、Jaesook Yun、Do Hyun Ryu

  DOI：10.1021/acs.orglett.7b03076

  日期：2017.12.1

  A highly enantioselective hydrosilylation of ketones was developed for the synthesis of a variety of chiral secondary alcohols. In the presence of a chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeded with good yields (up to 99%) with excellent enantioselectivities (up to 99% ee).

  酮的高度对映选择性氢化硅烷化被开发用于合成各种手性仲醇。在手性恶唑硼烷鎓离子（COBI）催化剂的存在下，反应以良好的收率（高达99％）和优异的对映选择性（高达99％ee）进行。
• [2+2] Photocycloaddition of 3-Alkenyloxy-2-cycloalkenones: Enantioselective Lewis Acid Catalysis and Ring Expansion
  作者：Richard Brimioulle、Thorsten Bach

  DOI：10.1002/anie.201407832

  日期：2014.11.17

  (50 mol %) of a chiral Lewis acid, the intramolecular [2+2] photocycloaddition of the title compounds was achieved with high enantioselectivity (up to 94 % ee). Upon cleavage of the cyclobutane ring the resulting tricyclic products underwent ring‐expansion reactions under acidic conditions and formed anellated seven‐ or eight‐membered‐ring systems without racemization. The ring expansion could be combined

  通过施加亚化学计量的量（50mol％）的手性路易斯酸，以高对映选择性（至多94％ee）实现了标题化合物的分子内[2 + 2]光环加成 。环丁烷环断裂后，所得三环产物在酸性条件下进行扩环反应，形成带外消旋作用的带电荷的七元或八元环系统。BF 3催化时，扩环可以与非对映选择性还原（三乙基硅烷）或烯丙基化（烯丙基三甲基硅烷）结合使用（产率48-87％）。
• Enantioselective Intermolecular [2+2] Photocycloaddition Reaction of Cyclic Enones and Its Application in a Synthesis of (−)-Grandisol
  作者：Saner Poplata、Thorsten Bach

  DOI：10.1021/jacs.8b01011

  日期：2018.3.7

  The intermolecular [2+2] photocycloaddition of typical cyclic α,β-unsaturated enones, such as 2-cyclohexenone, with olefins was performed in moderate to good yields (42–82%) and with high enantioselectivity (82%–96% ee). An unusual substitution pattern at the chiral oxazaborolidine-AlBr3 Lewis acid complex that promotes the reaction was found to be crucial for the success of the reaction. The method

  典型的环状 α,β-不饱和烯酮（如 2-环己烯酮）与烯烃的分子间 [2+2] 光环加成以中等至良好的产率（42-82%）和高对映选择性（82%-96% ee ）。发现促进反应的手性恶唑硼烷-AlBr3 路易斯酸络合物的不寻常取代模式对反应的成功至关重要。该方法用于对映选择性合成单萜(-)-格兰地醇，以3-甲基-2-环己烯酮为原料，可分六步完成，总产率为13%。
• Intramolecular [2+2] Photocycloaddition of Cyclic Enones: Selectivity Control by Lewis Acids and Mechanistic Implications
  作者：Saner Poplata、Andreas Bauer、Golo Storch、Thorsten Bach

  DOI：10.1002/chem.201901304

  日期：2019.6.18

  that attractive dispersion forces may be responsible for a change of the binding mode. The catalytic [2+2] photocycloaddition was shown to proceed on the triplet hypersurface with a quantum yield of 0.05. The positive effect of Lewis acids on the outcome of a given intramolecular [2+2] photocycloaddition was illustrated by optimizing the key step in a concise total synthesis of the sesquiterpene (±)‐italicene

  在存在λ = 366 nm的条件下进行辐照时，以对映选择性的方式进行3-烯基-2-环烯酮的分子内[2 + 2]光环加成反应（九个代表性实例，产率为54-86％，ee为76-96％ee）。 AlBr 3活化的恶唑硼烷作为路易斯酸。对脯氨酸衍生的恶唑硼烷的广泛筛选表明，对映体的分化很大程度上取决于杂环3位上芳基的性质。路易斯酸-底物复合物的DFT计算表明，有吸引力的分散力可能是改变结合模式的原因。催化的[2 + 2]光环加成反应在三重态超表面上进行，量子产率为0.05。通过优化倍半萜烯（±）-斜体的简明全合成中的关键步骤，可以说明路易斯酸对给定的分子内[2 + 2]光环加成反应的积极作用。
• Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer
  作者：Mary Elisabeth Daub、Hoimin Jung、Byung Joo Lee、Joonghee Won、Mu-Hyun Baik、Tehshik P. Yoon

  DOI：10.1021/jacs.9b04643

  日期：2019.6.19

  accelerates the transfer of triplet energy from an excited-state Ir(III) photocatalyst to the cinnamate ester. Computational evidence indicates that the principal role of the Lewis acid cocatalyst is to lower the absolute energies of the substrate frontier molecular orbitals, leading to greater electronic coupling between the sensitizer and substrate and increasing the rate of the energy transfer event. These

  我们报告了简单肉桂酸酯的对映选择性 [2+2] 环加成，其产物是用于环丁烷天然产物受控组装的有用合成子。该方法利用共催化系统，其中手性路易斯酸加速三线态能量从激发态 Ir(III) 光催化剂向肉桂酸酯的转移。计算证据表明，路易斯酸助催化剂的主要作用是降低底物前沿分子轨道的绝对能量，导致敏化剂和底物之间更大的电子耦合并增加能量转移事件的速率。这些结果表明路易斯酸可以对三线态敏化反应产生多种有益影响，影响德克斯特能量转移的热力学驱动力和动力学。