乙基 (2S)-2,3-环氧树脂丙烷酸酯 | 111058-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 乙基 (2S)-2,3-环氧树脂丙烷酸酯
• 中文别名: (2s)-23-环氧基丙酸乙酯；乙基(2S)-2,3-环氧树脂丙烷酸酯
• 英文名称: ethyl (S)-(-)-2,3-epoxypropanoate
• 英文别名: ethyl (S)-oxiranecarboxylate；(S)-(-)-glycidate d'ethyle；ethyl glycidate；ethyl (2S)-oxirane-2-carboxylate
• CAS: 111058-34-5
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: LSGWSXRILNPXKJ-BYPYZUCNSA-N

物化性质

• 沸点：
  68-69 °C (15 mmHg)
• 密度：
  1.180
• 闪点：
  45 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26
• 危险类别码：
  R22
• 储存条件：
  存放于0-6℃阴凉干燥处

SDS

Name:	Ethyl (2s)-2 3-epoxypropanoate 97% Material Safety Data Sheet
Synonym:	(-)-Ethyl (2S)-oxiranecarboxylate; (S)-(-)-Ethyl glycidat
CAS:	111058-34-5

Section 1 - Chemical Product MSDS Name:Ethyl (2s)-2 3-epoxypropanoate 97% Material Safety Data Sheet
Synonym:(-)-Ethyl (2S)-oxiranecarboxylate; (S)-(-)-Ethyl glycidat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
111058-34-5	Ethyl (2S)-2,3-epoxypropanoate, 97%	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.Hygroscopic (absorbs moisture from the air).
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. Get medical aid if cough or other symptoms appear.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.
Exposure Limits CAS# 111058-34-5: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear a chemical apron.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Clear
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 68 - 69 deg C @ 15.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H8O3
Molecular Weight: 116.11

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 111058-34-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl (2S)-2,3-epoxypropanoate, 97% - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 111058-34-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 111058-34-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 111058-34-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  乙基 (2S)-2,3-环氧树脂丙烷酸酯 在 咪唑 、 ytterbium(III) triflate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl (S)-2-((tert-butyldimethylsilyl)oxy)-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  [EN] SMALL MOLECULE INHIBITORS OF IL-6 AND USES THEREOF
  [FR] PETITES MOLÉCULES INHIBANT L'IL-6 ET LEURS UTILISATIONS

  摘要：

  本发明涉及取代的2-(1H-吲哚-3-基)乙醇类似物和取代的3,3a,8,8a-四氢-2H-呋喃[2,3-b]吲哚类似物、其衍生物和相关化合物，它们可用作抑制IL-6介导的Jak2/STAT3通路激活的抑制剂；制备这些化合物的合成方法；包括这些化合物的制药组合物；以及使用这些化合物和组合物治疗与IL6功能失调相关的细胞无控制增殖疾病的方法。本摘要旨在作为搜索特定领域的工具，并不意味着对本发明的限制。

  公开号：

  WO2013019690A1
• 作为产物：
  描述：

  (S)-环氧乙烷-2-羧酸钾 生成 乙基 (2S)-2,3-环氧树脂丙烷酸酯
  参考文献：
  名称：

  LARCHEVEQUE, MARC;PETIT, YVES, BULL. SOC. CHIM. FR.,(1989) N, C. 130-139

  摘要：

  DOI：

文献信息

• Investigate Natural Product Indolmycin and the Synthetically Improved Analogue Toward Antimycobacterial Agents
  作者：Yuhong Yang、Yuanyuan Xu、Yuan Yue、Heng Wang、Yumeng Cui、Miaomiao Pan、Xi Zhang、Lin Zhang、Haitao Li、Min Xu、Yefeng Tang、Shawn Chen

  DOI：10.1021/acschembio.1c00394

  日期：2022.1.21

  Indolmycin (IND) is a microbial natural product that selectively inhibits bacterial tryptophanyl-tRNA synthetase (TrpRS). The tryptophan biosynthesis pathway was recently shown to be an important target for developing new antibacterial agents against Mycobacterium tuberculosis (Mtb). We investigated the antibacterial activity of IND against several mycobacterial model strains. A TrpRS biochemical assay

  吲哚霉素 (IND) 是一种微生物天然产物，可选择性抑制细菌色氨酸-tRNA 合成酶 (TrpRS)。色氨酸生物合成途径最近被证明是开发针对结核分枝杆菌(Mtb) 的新型抗菌剂的重要目标。我们研究了 IND 对几种分枝杆菌模型菌株的抗菌活性。开发了一种 TrpRS 生化试验来分析合成 IND 类似物的文库。4″-甲基化 IND 化合物 Y-13 显示出改善的抗 Mtb 活性，最小抑制浓度 (MIC) 为 1.88 μM (~0.5 μg/mL)。当在基因工程替代牛分枝杆菌中诱导 TrpRS 过表达时，MIC 显着增加卡介苗。Mtb TrpRS 与 IND 和 ATP 复合的共晶结构表明氨基酸袋处于 apo 蛋白的开放形式和与反应中间体的封闭复合物之间的状态。在基于全细胞的实验中，我们研究了 Y-13 与不同抗菌剂的组合效果。我们通过基因组测序评估了杀伤动力学、对 IND 的抗性频率以及 IND
• An Efficient Route to α,β-Epoxy Ketones of High Enantiomerical Purity
  作者：L. Pégorier、Y. Petit、A. Mambu、M. Larchevêque

  DOI：10.1055/s-1994-25700

  日期：——

  Acylepoxides were obtained in high enantiomeric purity (ee = 92-99%) by addition of organolithium or Grignard reagents to enantiomerically pure methyl or ethyl 2,3-epoxypropanoates at low temperature ( - 85°C)

  通过在低温（-85°C）下将有机锂或格氏试剂添加到对映体纯的甲基或乙基2,3-环氧丙酸酯中，获得了高对映体纯度的酰基环氧化物（ee = 92-99%）。
• Total Synthesis of Solandelactone I
  作者：Nils C. Eichenauer、Roxanne Tschersich、Jörg Pietruszka

  DOI：10.1021/acs.jnatprod.5b00757

  日期：2015.11.25

  were combined in a Horner–Wadsworth–Emmons reaction to create two common intermediates for the stereodivergent synthesis of all four diastereomers 1–4 matching the proposed structure of solandelactone I. Comparison of the published analytical data of natural product solandelactone I and data obtained from the synthetic endeavor toward diastereomers 1–4 enabled the structure assignment of isomer 3; the

  由于海洋天然产物solandelactones A-I是从分离水螅Solanderia塞康达和由Seo等人调查。在1996年，人们对这些海洋上的脂蛋白进行了大量的合成研究。然而，苏糖内酯I的结构解析仍然不完全，并且没有合成的报道。在我们的逆合成分析的基础上，所述键积木合并在Horner-Wadsworth-Emmons反应，为所有四个非对映体的合成stereodivergent创建两个共同中间体1 - 4匹配solandelactone I.公布的比较的所提出的结构天然产物solandelactone I的分析数据以及从合成方法中获得的非对映异构体数据1– 4启用了异构体3的结构分配；拟议的海洋氧化脂生物合成途径也支持该结果。
• Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds
  作者：Marcela Krečmerová、Miloš Buděšínský、Milena Masojídková、Antonín Holý

  DOI：10.1135/cccc20030931

  日期：——

  Reaction of ethyl (R)-oxiranecarboxylate (2a) with various nucleobases (adenine, 6-chloropurine, thymine, cytosine, N⁶-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one and 4-methoxypyrimidin-2(1H)-one) afforded ethyl 3-substituted-2-hydroxypropanoates 4-10. Enantioselectivity of this reaction is dependent on the type of the base: 6-chloropurine, N⁶-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one, thymine and cytosine gave optically pure R enantiomers. In other cases, partial or complete racemization occurred. Optically pure ethyl (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoate (5a) was hydrolyzed to give (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoic acid (11). Reactions of 11 with various primary or secondary amines led to N⁶-substituted (R)-3-(adenin-9-yl)-2-hydroxypropanoic acids 14-19. Enantiomeric purity was determined from ¹H NMR spectra measured in the presence of (-)-(R)-1-(9-anthryl)-2,2,2-trifluoroethan-1-ol.

  乙基（R）-环氧丙酸乙酯（2a）与各种核碱基（腺嘌呤、6-氯嘌呤、胸腺嘧啶、胞嘧啶、N6-苯甲酰腺嘌呤、4-甲氧基-5-甲基嘧啶-2（1H）-酮和4-甲氧基嘧啶-2（1H）-酮）反应生成乙基3-取代-2-羟基丙酸酯4-10。该反应的对映选择性取决于碱基的类型：6-氯嘌呤、N6-苯甲酰腺嘌呤、4-甲氧基-5-甲基嘧啶-2（1H）-酮、胸腺嘧啶和胞嘧啶生成光学纯R对映异构体。在其他情况下，部分或完全消旋发生。光学纯乙基（R）-3-（6-氯嘌呤-9-基）-2-羟基丙酸酯（5a）水解得到（R）-3-（6-氯嘌呤-9-基）-2-羟基丙酸（11）。11与各种一级或二级胺的反应导致N6-取代（R）-3-（腺嘌呤-9-基）-2-羟基丙酸14-19。对映纯度是通过在(-)-（R）-1-（9-蒽基）-2,2,2-三氟乙醇存在下测定的1H NMR谱来确定的。
• A simple preparation of R or S glycidic esters; Application to the synthesis of enantiomerically pure α-hydroxyesters.
  作者：Marc Larchevêque、Yves Petit

  DOI：10.1016/s0040-4039(00)96028-3

  日期：1987.1

  The simple preparation of enantiomerically pure α-hydroxyesters by the régioselective reaction of lithio and magnesiocuprates with glycidic esters or ′ readily available from serine is described.

  描述了通过硫代和镁代高铁酸盐与容易从丝氨酸获得的缩水甘油酯或′的区域选择性反应来简单制备对映体纯的α-羟基酯的方法。