3-chloro-4-oxo-pentanoic acid ethyl ester | 59865-89-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-chloro-4-oxo-pentanoic acid ethyl ester
• 英文别名: 3-Chlor-4-oxo-valeriansaeure-aethylester；Pentanoic acid, 3-chloro-4-oxo-, ethyl ester；ethyl 3-chloro-4-oxopentanoate
• CAS: 59865-89-3
• 化学式: C₇H₁₁ClO₃
• 分子量: 178.616
• InChiKey: RJBDUUAORCLODD-UHFFFAOYSA-N

物化性质

• 沸点：
  95-97 °C(Press: 12 Torr)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-4-oxo-pentanoic acid ethyl ester 在 sodium hydroxide 、 potassium bromide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 25.42h， 生成 2-(4-methyl-2-phenoxymethyl-thiazol-5-yl)-N-phenyl-acetamide
  参考文献：
  名称：

  Abdel-Lateef,M.F.-A. et al., Roczniki Chemii, 1976, vol. 50, p. 323 - 327

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酸乙酯 在 磺酰氯 、 苯 作用下， 生成 3-chloro-4-oxo-pentanoic acid ethyl ester
  参考文献：
  名称：

  Thiamin Analogs. III. 4-Methyl-5-(hydroxymethyl)-thiazole¹

  摘要：

  DOI：

  10.1021/ja01219a013

文献信息

• Method for obtaining 5-halogenolaevulinic acid alkyl esters
  申请人：Aldenkortt Dr Sven

  公开号：US20050070727A1

  公开（公告）日：2005-03-31

  A method for obtaining a 5-bromolevulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester from either a bromination mixture or a chlorination mixture, containing either a 5-bromo-levulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester, respectively, produced by either brominating or chlorinating levulinic acid or a levulinic acid methyl ester, and further including the steps of dissolving the bromination or chlorination mixture in an organic solvent or solvent mixture and cooling the solution, preferably to −20° C.-−40° C., with the 5-bromolevulinic acid methyl ester or 5-chlorolaevulinic acid methyl ester being crystallized out of the solution. The 5-bromolevulinic acid methyl ester or 5-chlorolevulinic acid is then isolated by draining off the solution with the remaining bromination mixture or chlorination mixture, as appropriate.

  从溴化混合物或氯化混合物中获取5-溴丙酮酸甲酯或5-氯丙酮酸甲酯的方法，分别包含5-溴丙酮酸甲酯或5-氯丙酮酸甲酯，这些物质是通过溴化或氯化丙酮酸或丙酮酸甲酯产生的。进一步包括将溴化或氯化混合物溶解在有机溶剂或溶剂混合物中，并冷却溶液，最好冷却至-20°C至-40°C，其中5-溴丙酮酸甲酯或5-氯丙酮酸甲酯从溶液中结晶出来。然后通过排出剩余的溴化混合物或氯化混合物，分离出5-溴丙酮酸甲酯或5-氯丙酮酸甲酯。
• Emery, Journal fur praktische Chemie (Leipzig 1954), 1896, vol. <2> 53, p. 310
  作者：Emery

  DOI：——

  日期：——
• Asymmetric reduction of chlorinated 4-oxopentanoates with Bakers' yeast. Synthesis of optically active .gamma.-butyrolactones and useful chiral building blocks
  作者：Sadao Tsuboi、Junichi Sakamoto、Takayuki Kawano、Masanori Utaka、Akira Takeda

  DOI：10.1021/jo00025a043

  日期：1991.12
• Conrad; Guthzeit, Chemische Berichte, 1886, vol. 19, p. 43
  作者：Conrad、Guthzeit

  DOI：——

  日期：——
• Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3A<i>S</i>,6a<i>S</i>)-Ethisolide, Whisky Lactone, and (−)-Avenaciolide
  作者：Sadao Tsuboi、Jun-ichi Sakamoto、Hiroshi Yamashita、Takashi Sakai、Masanori Utaka

  DOI：10.1021/jo970045r

  日期：1998.2.1

  Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydraxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (gamma S)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (+/-)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (gamma R)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.