(S)-(-)-2-异氰酰基戊二酸二乙酯 | 145080-95-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (S)-(-)-2-异氰酰基戊二酸二乙酯
• 英文名称: (S)-(-)-2-isocyanatoglutaric acid diethyl ester
• 英文别名: diethyl (S)-2-isocyanatopentanedioate；diethyl (S)-(-)-2-isocyanatoglutarate；L-2-Isocyanato-glutarsaeure-diaethylester；diethyl (2S)-2-isocyanatoglutarate；(S)-2-Isocyanato-glutarsaeure-diaethylester；N-Carbonyl-L-glutaminsaeure-diaethylester；N-carbonyl-L-glutamic acid diethyl ester；diethyl (2S)-2-isocyanatopentanedioate
• CAS: 145080-95-1
• 化学式: C₁₀H₁₅NO₅
• 分子量: 229.233
• InChiKey: TZTLQVZEVNEAQD-QMMMGPOBSA-N

物化性质

• 沸点：
  151 °C / 10mmHg
• 密度：
  1,13 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2929109000
• 安全说明：
  S26,S36,S37,S39
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P261,P270,P271,P264,P280,P337+P313,P305+P351+P338,P361+P364,P332+P313,P301+P310+P330,P302+P352+P312,P304+P340+P311,P403+P233,P405
• 危险品运输编号：
  2810
• 危险性描述：
  H301+H311+H331,H315,H319
• 储存条件：
  保存方法：将它们存放在冰箱内。

SDS

Diethyl (S)-(-)-2-Isocyanatoglutarate Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Diethyl (S)-(-)-2-Isocyanatoglutarate

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 4
Category 4
Acute toxicity (Inhalation)
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
Specific target organ toxicity Respiratory tract irritation
- Single exposure [Category 3]
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Warning
Signal word
Hazard statements Harmful if swallowed or if inhaled
Causes skin irritation
Causes serious eye irritation
May cause respiratory irritation
Precautionary statements:
Avoid breathing dust/fume/gas/mist/vapours/spray.
[Prevention]
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
Diethyl (S)-(-)-2-Isocyanatoglutarate

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Section 2. HAZARDS IDENTIFICATION
[Response] IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
breathing. Call a POISON CENTER or doctor/physician if you feel unwell.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
IF IN EYES: 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.
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.
Call a POISON CENTER or doctor/physician if you feel unwell.
[Storage] Store in a well-ventilated place. Keep container tightly closed.
Store locked up.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Diethyl (S)-(-)-2-Isocyanatoglutarate
Components:
Percent: >97.0%(GC)
CAS Number: 145080-95-1
Synonyms: Diethyl (S)-(-)-2-Isocyanatopentanedioate , (S)-(-)-2-Isocyanatoglutaric Acid Diethyl
Ester , (S)-(-)-2-Isocyanatopentanedioic Acid Diethyl Ester
Chemical Formula: C10H15NO5

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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.
Call a POISON CENTER or doctor/physician if you feel unwell.
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: Call a POISON CENTER or doctor/physician 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:
Unsuitable extinguishing Solid streams of water
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 extra personal protective equipment (self-contained breathing apparatus). Keep
protective equipment and people away from and upwind of spill/leak. Ensure adequate ventilation. Entry to non-
emergency procedures: involved personnel should be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Diethyl (S)-(-)-2-Isocyanatoglutarate

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Section 6. ACCIDENTAL RELEASE MEASURES
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with 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 generation of vapour or mist. Wash hands and face thoroughly after
handling.
Use a closed system if possible. Use a ventilation, local exhaust if vapour 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 refrigerator.
Store under inert gas.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive, Air-sensitive
Comply with laws.
Packaging material:

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Half or full facepiece respirator, self-contained breathing apparatus(SCBA), supplied
air respirator, etc. Use respirators approved under appropriate government standards
and follow local and national regulations.
Impervious gloves.
Hand protection:
Eye protection: Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Very pale yellow - Yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: 151°C/1.3kPa
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 1.13
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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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
Diethyl (S)-(-)-2-Isocyanatoglutarate

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Section 10. STABILITY AND REACTIVITY
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
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:
No data available
Fish:
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
No data available
Soil adsorption (Koc):
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 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
Not listed
UN-No:

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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.
Diethyl (S)-(-)-2-Isocyanatoglutarate

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-异氰酰基戊二酸二乙酯 以 水 、 丙酮 为溶剂， 生成 N,N'-carbonyl-di-L-glutamic acid tetraethyl ester
  参考文献：
  名称：

  Formation and Properties of Isocyanates Derived from Amino Ester Hydrochlorides

  摘要：

  DOI：

  10.1021/jo01351a088
• 作为产物：
  描述：

  L-谷氨酸二乙酯盐酸盐 、 氯甲酸三氯甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (S)-(-)-2-异氰酰基戊二酸二乙酯
  参考文献：
  名称：

  一种雷替曲塞关键中间体的合成工艺

  摘要：

  本发明涉及医药制备技术领域，特别涉及一种雷替曲塞关键中间体的合成工艺。本发明所设计的一种雷替曲塞关键中间体的合成工艺，通过先将谷氨酸二乙酯形成活性中间体(异氰酸酯)，然后与N‑甲基‑(2‑噻吩基)氨基甲酸叔丁酯直接反应，两步制得目标产物——N‑[5‑[N‑(叔丁氧羰基)‑N‑甲基氨基]‑2‑噻吩甲酰]‑L‑谷氨酸二乙酯。本发明规避了酰胺化反应导致手性中心部分消旋的潜在风险、收率较低、操作和纯化繁琐等难点，提供了一种操作简单、路线简短、环境友好和收率高的雷替曲塞关键中间体的合成工艺。

  公开号：

  CN109734698B

文献信息

• Inhibitors of protein tyrosine phosphatase
  申请人：Pharmacia & Upjohn Company

  公开号：US06353023B1

  公开（公告）日：2002-03-05

  The present invention comprises small molecular weight, non-peptidic inhibitors of formula I and II of Protein Tyrosine Phosphatase 1 (PTP1) which are useful for the treatment and/or prevention of Non-Insulin Dependent Diabetes Mellitus (NIDDM).

  本发明涉及小分子量、非肽类的蛋白酪氨酸磷酸酶1（PTP1）的化学式I和II的抑制剂，用于治疗和/或预防非胰岛素依赖型糖尿病（NIDDM）。
• Synthetic Approaches To Obtain Amino Acid Adducts of 4,4′-Methylenediphenyl Diisocyanate
  作者：Gabriele Sabbioni、Nagaraju Dongari、Siegfried Schneider、Anoop Kumar

  DOI：10.1021/tx300347e

  日期：2012.12.17

  obtain amino acid adducts of MDI. We synthesized and isolated MDI adducts of aspartic acid, glutamic acid, cysteine, and valine. The new adducts were characterized by LC-MS/MS and NMR. We synthesized the corresponding isotope-labeled MDI adducts to develop analytical methods using LC-MS/MS. Glutathione adducts of isocyanates are an important way of transportation of the reactive isocyanates to distant

  4,4'-亚甲基二苯基二异氰酸酯（MDI）是化学工业中最重要的异氰酸酯。暴露于MDI后，肺部过敏和哮喘是主要的损害类型。MDI的白蛋白加合物可能与致敏反应的病因有关。因此，必须有敏感的和特定的生物标记物，例如血液蛋白加合物，以监测暴露于异氰酸酯的人。为了发现体内存在的血液蛋白与新的异氰酸酯加合物，需要新的合成标准品。为此，我们开发了五种方法来获得MDI的氨基酸加合物。我们合成并分离了天冬氨酸，谷氨酸，半胱氨酸和缬氨酸的MDI加合物。新的加合物通过LC-MS / MS和NMR进行表征。我们合成了相应的同位素标记的MDI加合物，以开发使用LC-MS / MS的分析方法。异氰酸酯的谷胱甘肽加合物是将反应性异氰酸酯转移到远离原始暴露部位的较远部位的一种重要方式。因此，我们使用了MDI的N-乙酰基-半胱氨酸加成物：N-乙酰基-S [[[4-（4-氨基苄基）苯基]氨基甲酰基]-半胱氨酸（MDI-AcCys）和N-乙酰基-S
• Structure–activity relationships of succinimidyl-Cys-C(O)-Glu derivatives with different near-infrared fluorophores as optical imaging probes for prostate-specific membrane antigen
  作者：Daiko Matsuoka、Hiroyuki Watanabe、Yoichi Shimizu、Hiroyuki Kimura、Yusuke Yagi、Ryoko Kawai、Masahiro Ono、Hideo Saji

  DOI：10.1016/j.bmc.2018.03.015

  日期：2018.5

  target for imaging and therapy of PCa. We previously reported a PSMA imaging probe, 800CW-SCE, based on succinimidyl-Cys-C(O)-Glu (SCE) for optical imaging of PCa. In this study, we investigated the structure–activity relationships of novel SCE derivatives with five different near-infrared (NIR) fluorophores (IRDye 680LT, IRDye 750, Indocyanine Green, Cyanine 5.5, and Cyanine 7) as optical imaging probes

  在恶性前列腺癌（PCa）中过表达的前列腺特异性膜抗原（PSMA）是PCa成像和治疗的理想靶标。我们以前曾报道过一种基于琥珀酰亚胺基-Cys-C（O）-Glu（SCE）的PSMA成像探头800CW-SCE，用于PCa的光学成像。在这项研究中，我们研究了具有五个不同近红外（NIR）荧光团（IRDye 680LT，IRDye 750，吲哚菁绿，花菁5.5和花菁7）作为针对PSMA的光学成像探针的新型SCE衍生物的结构-活性关系。一种在体外结合测定显示800CW-SCE，680LT-SCE和750-SCE的结合亲和力比2-PMPA（称为PSMA抑制剂）的结合亲和力高。这三种SCE衍生物被内在化为PSMA阳性细胞（LNCaP细胞），而不是内化为PSMA阴性细胞（PC-3细胞）。在体内成像研究中，LNCaP肿瘤中高度积累了800CW-SCE和750-SCE，而PC-3肿瘤中却没有积累800CW-SCE和800CW-SCE的LNCaP
• SUBSTITUTED INDOLE AND AZAINDOLE OXOACETYL PIPERAZINAMIDE DERIVATIVES
  申请人：Wang Tao

  公开号：US20120202775A1

  公开（公告）日：2012-08-09

  Compounds having drug and bio-affecting properties are described herein, including their properties, pharmaceutical compositions and methods of use. In particular, tricyclic aryl or heteroaryl piperazine diamide derivatives that possess unique antiviral activity are set forth. These compounds are useful for the treatment of HIV and AIDS. The compounds herein have the general Formula I: wherein: Y is selected from the group of indole or azaindole systems: and Z is selected from the group of:

  本文描述了具有药物和生物影响特性的化合物，包括它们的特性、制药组合物和使用方法。特别地，本文阐述了具有独特抗病毒活性的三环芳基或杂芳基哌嗪二酰胺衍生物。这些化合物可用于治疗艾滋病毒和艾滋病。本文中的化合物具有通用的I式：其中：Y选自吲哚或氮杂吲哚系统的群体；Z选自：
• N,N-Bis(2-chloroethyl)carbamoyl Derivatives of L-Amino Acids. New Potential Antitumor Agents with Latent Activity^1,2
  作者：Ezra Khedouri、Young-Ho Kim、Orrie M. Friedman

  DOI：10.1021/jm00335a020

  日期：1964.9