(S)-(-)-3-(N-甲氨基)-1-(2-噻吩基)-1-丙醇 | 116539-55-0

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (S)-(-)-3-(N-甲氨基)-1-(2-噻吩基)-1-丙醇
• 中文别名: (S)-N-甲胺基-1-(2-噻吩)-1-丙醇；(s)-(-)-N-甲基-3-羟基-(2-噻吩)丙胺；S-(-)N-甲基-3-羟基-3-(2-噻吩基)丙胺；(S)-3-(甲氨基)-1-(2-噻吩基)-1-丙醇；3-甲基氨基-1-(2-噻吩基)-1-丙醇；(S)-3-甲基氨基-1-(2-噻吩基)-1-丙醇；S-(-)-3-甲氨基-1-(2-噻吩基)-1-丙醇
• 英文名称: (S)-3-methylamino-1-(2-thienyl)-1-propanol
• 英文别名: (S)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol；(1S)-3-(methylamino)-1-(thien-2-yl)-1-propanol；(S)-(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol；(1S)-3-(methylamino)-1-thiophen-2-ylpropan-1-ol
• CAS: 116539-55-0
• 化学式: C₈H₁₃NOS
• 分子量: 171.263
• InChiKey: YEJVVFOJMOHFRL-ZETCQYMHSA-N

物化性质

• 熔点：
  72.0 to 76.0 °C
• 沸点：
  294.3±35.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储条件为2～8℃，需在惰性气体氛围下进行。

SDS

(S)-3-(Methylamino)-1-(2-thienyl)-1-propanol Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: (S)-3-(Methylamino)-1-(2-thienyl)-1-propanol

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: (S)-3-(Methylamino)-1-(2-thienyl)-1-propanol
Percent: >98.0%(GC)(T)
CAS Number: 116539-55-0
Synonyms: (S)-2-[3-(Methylamino)-1-hydroxypropyl]thiophene
C8H13NOS
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: Very pale yellow - Pale reddish yellow
No data available
Odour:

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:74°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Methanol

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents, Strong acids
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

性质

3-甲基氨基-1-(2-噻吩基)-1-丙醇在常温常压下呈现灰白色或粉色固体。

用途

3-甲基氨基-1-(2-噻吩基)-1-丙醇是合成度洛西汀（一种选择性的5-羟色胺(5-HT)和去甲肾上腺素(NE)再摄取抑制药）的中间体。度洛西汀具有抗抑郁和中枢镇痛作用，其具体机制尚不明确，但被认为与其增强中枢神经系统中的5-羟色胺能与去甲肾上腺素能功能有关。

制备方法

在1升四颈烧瓶中加入N-甲基-N-异丁氧基羰基-3-羟基-3-(2-噻吩基)丙胺114.8毫克（0.42毫摩尔）、2-丙醇5毫升和体积分数为30%的氢氧化钠水溶液0.2克，反应温度控制在30度，反应24小时后完成。随后浓缩反应液，并用乙酸乙酯进行萃取以去除残留物。合并后的乙酸乙酯层经无水硫酸钠干燥处理，真空旋干溶剂。最后通过硅胶柱色谱法纯化得到目标产物3-甲基氨基-1-(2-噻吩基)-1-丙醇，总产率为92%。

反应信息

• 作为反应物：
  描述：

  (S)-(-)-3-(N-甲氨基)-1-(2-噻吩基)-1-丙醇 在 potassium phosphate 、 copper(l) iodide 、 sodium hydride 、 N,N-二异丙基乙胺 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 43.5h， 生成 2-(trimethylsilyl)ethyl (S)-(3-(3-(8-(ethylamino)-1-methyl-5-oxo-1,2,3,5-tetrahydro-4H-pyrido[4,3-e][1,4]diazepin-4-yl)phenoxy)-3-(thiophen-2-yl)propyl)(methyl)carbamate
  参考文献：
  名称：

  双环二氮杂酮为电压门控钙通道α2δ-1亚基的双配体和去甲肾上腺素转运蛋白

  摘要：

  合成和一系列新的双环二氮杂酮与向电压门控钙通道的α2δ-1亚单位的双活性（钙的药理活性v报告α2δ-1）和去甲肾上腺素转运蛋白（NET）。的位置的探索适合用于在nonaminoacidic的Ca取代v α2δ-1的支架允许有利的位置的识别为NET药效的附接。在探索的模式中，2-乙基氨基-9-甲基-6-苯基-6,7,8,9-四氢-5 H-嘧啶的连接[4,5- e在3-甲基氨基-1-苯基丙氧基和3-甲基氨基-1-硫代苯基丙氧基部分的苯环的间位] [1,4]二氮杂-5-酮骨架提供了具有出色NET功能的双化合物。还探索了替代性双环框架，并鉴定了一些铅分子，这些铅分子显示出平衡的双重分布并显示出良好的ADMET性能。

  DOI：

  10.1021/acs.jmedchem.0c01867
• 作为产物：
  描述：

  2-噻吩甲酸 在 RuBr₂((R)-(6,6'-(MeO)2-biphenyl-2,2'-diyl)bis(Ph₂-phosphane) lithium aluminium tetrahydride 、 氢气 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， -10.0~65.0 ℃ 、101.33 kPa 条件下， 反应 107.5h， 生成 (S)-(-)-3-(N-甲氨基)-1-(2-噻吩基)-1-丙醇
  参考文献：
  名称：

  使用手性二膦-钌配合物对β-酮酯进行对映选择性加氢：用于学术和工业目的及合成应用的优化

  摘要：

  使用对映异构体二膦与钌之间的手性配合物进行对映选择性氢化是生产手性化合物的有力工具。使用简单直接的原位催化剂制备方法，出于学术和工业目的，使用分子氢对条件进行了优化。这导致所用压力所需的最佳条件和最低催化比。各种β-酮酯的氢化反应均在大气压和较高压力下有效进行，从而导致使用非常低的催化剂/底物比例，最高可达1 / 20,000。不对称氢化用于关键步骤，以合成胭脂红酸，度洛西汀和氟西汀。

  DOI：

  10.1002/adsc.200390021

文献信息

• 一种度洛西汀中间体的合成方法
  申请人：重庆常捷医药有限公司

  公开号：CN108341797B

  公开（公告）日：2021-04-27

  本发明是一种度洛西汀中间体(S)‑N‑甲基‑3‑羟基‑3‑(2‑噻吩基)‑1_丙胺（化合物1）的新合成方法。所述方法以噻吩和丁二酸酐为原料，经过傅克酰化，酯化，氨解，不对称氢化，氧化降解得到度洛西汀中间体（化合物1）。
• 중간체로서 광학 활성 3-아미노-1-프로판올 유도체의 제조방법 및 상기 중간체를 이용한 (S)-둘록세틴의 제조방법
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20150043955A

  公开（公告）日：2015-04-23

  본 발명에 따른 높은 광학 활성을 가지는 3-아미노-1-프로판올 유도체의 제조방법 및 이를 이용한 거울상 이성질체적으로 순수한 둘록세틴의 제조방법은 광학 활성을 가지는 3-아미노-1-프로판올 유도체를 종래의 어떤 방법보다도 더 높은 수율과 광학적 순도(ee)로 수득할 수 있으며, 이를 중간체로 이용함으로써 거울상 이성질체적으로 순수하며 높은 광학적 순도(ee)로 둘록세틴을 제조할 수 있다.

  根据本发明，具有高光学活性的3-氨基-1-丙醇衍生物的制备方法以及利用该方法制备高光学纯度的镜像立体异构体的方法，通过利用具有高光学活性的3-氨基-1-丙醇衍生物，可以比传统方法获得更高的产率和光学纯度（ee），并且可以利用其作为中间体制备出具有镜像立体异构体纯度和高光学纯度（ee）的二乙酰胺。
• 1,2‐Dihydro‐1‐hydroxy‐2,3,1‐benzodiazaborine Bearing an Acridine Moiety as a Circular Dichroism Probe for Determination of Absolute Configuration of Mono‐Alcohols
  作者：Shunsuke Shimo、Kohei Takahashi、Nobuharu Iwasawa

  DOI：10.1002/chem.201900350

  日期：2019.3.12

  A new chiral probe molecule for mono‐alcohols is developed by using 1,2‐dihydro‐1‐hydroxy‐2,3,1‐benzodiazaborine (DAB) bearing an acridine moiety 1. In the presence of mono‐alcohols, DAB 1 forms borate 2 by boronic ester formation, followed by coordination of the acridine moiety to the boron atom. Borate 2 has a chiral center on the boron atom and works as a stereodynamic circular dichroism (CD) probe

  通过使用带有bearing啶基1的1,2-二氢-1-羟基-2,3,1-苯并二氮杂硼烷（DAB），开发了一种新的一元醇手性探针分子。在一元醇的存在下，DAB 1形式硼酸2由硼酸酯形成，随后吖部分与硼原子配位。硼酸盐2在硼原子上有一个手性中心，并基于the啶基团与一元醇上碳-碳不饱和基团之间的π-π相互作用，用作手性一元醇的立体动力学圆二色性（CD）探针分子。
• [EN] RUTHENIUM COMPLEX AND METHOD FOR PREPARING OPTICALLY ACTIVE ALCOHOL COMPOUND<br/>[FR] COMPLEXE DE RUTHÉNIUM ET PROCÉDÉ POUR PRÉPARER UN COMPOSÉ ALCOOLIQUE OPTIQUEMENT ACTIF
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2011135753A1

  公开（公告）日：2011-11-03

  The present invention provides a novel ruthenium complex which has an excellent catalytic activity in terms of reactivity for asymmetric reduction of a carbonyl compound and enantioselectivity, a catalyst using the ruthenium complex, and a method for preparing optically active alcohol compounds using the ruthenium complex. The present invention relates to a ruthenium complex having ruthenacycle structure, a catalyst for asymmetric reduction consisting of the ruthenium complex, and a method for preparing optically active alcohol using the ruthenium complex.

  本发明提供了一种新型钌配合物，其在对羰基化合物的不对称还原反应活性和对映选择性方面具有优异的催化活性，以及使用该钌配合物的催化剂和制备光学活性醇化合物的方法。本发明涉及具有钌环结构的钌配合物，由该钌配合物组成的不对称还原催化剂，以及使用该钌配合物制备光学活性醇的方法。
• 광학 활성 3-클로로-1-아릴프로판-1-올 유도체로부터 3-아미노-1-아릴프로판-1-올 유도체의 제조방법
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20160044117A

  公开（公告）日：2016-04-25

  본 발명은 요오드화합물 존재 하에 광학 활성 3-클로로-1-아릴프로판-1-올 화합물을 아민 유도체와 반응시키는 단계를 포함하는, 광학 활성 3-아미노-1-아릴프로판-1-올 유도체의 제조방법에 관한 것이다. 본 발명의 제조방법은 단일 단계의 반응으로 광학 활성 3-클로로-1-아릴프로판-1-올 유도체를 직접 아민화하여 3-아미노-1-아릴프로판-1-올 유도체로 전환하므로 반응물의 광학 순도를 유지하면서 간단한 공정을 통해 높은 수율로 다양한 광학 활성 분자의 핵심 중간체가 되는 화합물을 제공할 수 있다. 따라서, 상기 제조방법을 높은 광학 순도로 본 발명의 제조방법에서 반응물로 사용되는 광학 활성 3-클로로-1-아릴프로판-1-올 유도체를 제조하는 방법 및 추가적인 치환반응과 조합함으로써 높은 광학 순도로 (S)-둘록세틴, (R)-플록세틴, (R)-토목세틴 또는 (R)-니속세틴 등의 약물을 제조하는 데 유용하게 사용될 수 있다.

  这项发明涉及一种在碘化合物存在下，将光学活性的3-氯-1-芳基丙烷-1-醇化合物与胺衍生物反应的步骤，涉及制备光学活性的3-氨基-1-芳基丙烷-1-醇衍生物的方法。该制备方法通过单步反应直接将光学活性的3-氯-1-芳基丙烷-1-醇衍生物氨化为3-氨基-1-芳基丙烷-1-醇衍生物，从而提供一种化合物，该化合物可通过简单工艺以高产率保持反应物的光学纯度，成为各种光学活性分子的重要中间体。因此，通过本发明的制备方法，可以制备用于制备高光学纯度(S)-多洛克赛汀、(R)-普洛克赛汀、(R)-托莫克赛汀或(R)-尼索克赛汀等药物的光学活性3-氯-1-芳基丙烷-1-醇衍生物的方法，并且可以通过进一步的取代反应和组合以高光学纯度制备这些药物。