2-氯-3,4-环氧-1-丁烯 | 3132-77-2

• 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: 2-氯-3,4-环氧-1-丁烯
• 英文名称: rac-(1-chloroethenyl)oxirane
• 英文别名: (+/-)-(1-chloroethenyl)oxirane；2-chloro-3,4-epoxy-1-butene；3-Chlor-1,2-epoxy-buten-(3)；2-Chloro-3,4-epoxybut-1-en；(1-chloro-vinyl)-oxirane；(1-Chlor-vinyl)-oxiran；(1-Chloroethenyl)oxirane；2-(1-chloroethenyl)oxirane
• CAS: 3132-77-2
• 化学式: C₄H₅ClO
• 分子量: 104.536
• InChiKey: JUFJKQAEILBFHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2910900090

反应信息

• 作为反应物：
  描述：

  2-氯-3,4-环氧-1-丁烯 在 水 作用下， 以 甲酸 为溶剂， 反应 3.5h， 以46%的产率得到rac-3-chlorobut-3-ene-1,2-diol
  参考文献：
  名称：

  In Vitro Metabolism of Chloroprene:  Species Differences, Epoxide Stereochemistry and a De-chlorination Pathway

  摘要：

  Chloroprene (1) was metabolized by liver microsomes from Sprague-Dawley rats, Fischer 344 rats, B6C3F1 mice, and humans to the monoepoxides, (1-chloro-ethenyl)oxirane (5a/5b), and 2-chloro-2-ethenyloxirane (4a/4b). The formation of 4a/4b was inferred from the identification of their degradation products. With male Sprague-Dawley and Fischer 344 rat liver microsomes, there was a ca. 3:2 preference for the formation of (R)-(1-chloroethenyl)oxirane (5a) compared to the (S)-enantiomer (5b). A smaller but distinct enantioselectivity in the formation of (S)-(1-chloro-ethenyl)oxirane occurred with liver microsomes from male mouse (R:S, 0.90:1) or male human (R:S, 0.86:1). 2-Chloro-2-ethenyloxirane was very unstable in the presence of the microsomal mixture and was rapidly converted to 1-hydroxybut-3-en-2-one (11) and 1-chlorobut-3-en-2-one (12). An additional rearrangement pathway of 2-chloro-2-ethenyloxirane gave rise to 2-chlorobut-3-en-1-al (14) and 2-chlorobut-2-en-1-al (15). Further reductive metabolism of these metabolites occurred to form 1-hydroxybutan-2-one (17) and 1-chlorobutan-2-one (18). In the absence of an epoxide hydrolase inhibitor, the microsomal incubations converted (1-chloroethenyl)oxirane to 3-chlorobut-3-ene-1,2-diol (21a/21b). When microsomal incubations were supplemented with glutathione, 1-hydroxybut-3-en-2-one was not detected because of its rapid conjugation with this thiol scavenger.

  DOI：

  10.1021/tx0155404
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 2-氯-3,4-环氧-1-丁烯
  参考文献：
  名称：

  Petrow, Zhurnal Obshchei Khimii, 1939, vol. 9, p. 2238

  摘要：

  DOI：

文献信息

• Process for the preparation of (1-chloroethenyl-) oxirane
  申请人：Bayer Aktiengesellschaft

  公开号：US04146544A1

  公开（公告）日：1979-03-27

  An improved process has been invented for the production of (1-chloroethenyl)-oxirane which comprises dehydrochlorinating (1,2-dichloroethyl)-oxirane with a solution of the sodium salt of an alcohol having at least 5 carbon atoms in said alcohol and separating the (1-chloro-ethenyl)-oxirane from the reaction mixture.

  已发明了一种改进的工艺，用于生产（1-氯乙烯基）-环氧乙烷，该工艺包括用至少含有5个碳原子的醇的钠盐溶液去氯化脱氢（1,2-二氯乙基）-环氧乙烷，并从反应混合物中分离出（1-氯乙烯基）-环氧乙烷。
• Identification of Adducts Derived from Reactions of (1-Chloroethenyl)oxirane with Nucleosides and Calf Thymus DNA
  作者：Tony Munter、Lisa Cottrell、Stuart Hill、Leif Kronberg、William P. Watson、Bernard T. Golding

  DOI：10.1021/tx020070e

  日期：2002.12.1

  rubbers. The reactions of (1-chloroethenyl)oxirane with 2'-deoxyguanosine, 2'-deoxyadenosine, 2'-deoxycytidine, thymidine, and calf thymus DNA have been studied in aqueous buffered solutions. The adducts from the nucleosides were isolated by reversed-phase HPLC, and characterized by their UV absorbance and (1)H and (13)C NMR spectroscopic and mass spectrometric features. The reaction with 2'-deoxyguanosine

  （1-氯乙烯基）环氧乙烷是氯丁二烯的主要诱变产物，氯丁二烯是一种重要的大规模石油化工产品，用于制造合成橡胶。在水溶液缓冲液中研究了（1-氯乙烯基）环氧乙烷与2'-脱氧鸟苷，2'-脱氧腺苷，2'-脱氧胞苷，胸苷和小牛胸腺DNA的反应。通过反相HPLC从核苷中分离出加合物，并通过其紫外吸收和（1）H和（13）C NMR光谱和质谱特征对其进行表征。与2'-脱氧鸟苷的反应产生了一个主要加合物N7-（3-氯-2-羟基-3-丁烯-1-基）-鸟嘌呤（dGI）和八个次要加合物，它们被确定为N1-的非对映异构体对（3-氯-2-羟基-3-丁烯-1-基）-2'-脱氧鸟苷（dGII，dGIII），N3，N7-双（3-氯-2-羟基-3-丁烯-1-基） -鸟嘌呤（dGIV，dGV），N7，N9-双（3-氯-2-羟基-3-丁烯-1-基）鸟嘌呤（dGVI，dGVII）和N1，N7-双（3-氯-2-羟基-3-羟基丁烯-1-
• Khazemova,L.A.; Al'bitskaya,V.M., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 1873 - 1876
  作者：Khazemova,L.A.、Al'bitskaya,V.M.

  DOI：——

  日期：——
• Al'biskaya,V.M. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 3704
  作者：Al'biskaya,V.M. et al.

  DOI：——

  日期：——
• Zaitseva,G.I.; Al'bitskaya,V.M., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 1987
  作者：Zaitseva,G.I.、Al'bitskaya,V.M.

  DOI：——

  日期：——