(E)-2-methyl-3-(2-methylsulfanyl-1,3-thiazol-4-yl)prop-2-enal | 252205-99-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-2-methyl-3-(2-methylsulfanyl-1,3-thiazol-4-yl)prop-2-enal
• CAS: 252205-99-5
• 化学式: C₈H₉NOS₂
• 分子量: 199.298
• InChiKey: ZMNMZOJFWZFEMF-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-3-(2-methylsulfanyl-1,3-thiazol-4-yl)prop-2-enal 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (E)-3-Fluoro-4-hydroxy-5-methyl-6-(2-methylsulfanyl-thiazol-4-yl)-hex-5-en-2-one
  参考文献：
  名称：

  Regioselective synthesis of fluoroaldols. Studies toward fluoroepothilones syntheses via antibody catalysis

  摘要：

  A general method for the synthesis of fluoromethyl aldols has been developed. Tributylboron enolates of fluoroacetone react with thiazole aldehydes (6) to provide fluoromethylaldols (4) regioselectively in high yields. Regioisomeric fluoroaldols (5) are produced as a 1:1 isomeric mixture of the erythro and three products via a two-step procedure: first, aldol reaction with Weinreb amide and then Grignard reaction. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01469-6
• 作为产物：
  描述：

  ethyl 2-(methylsulfanyl)-1,3-thiazole-4-carboxylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 (E)-2-methyl-3-(2-methylsulfanyl-1,3-thiazol-4-yl)prop-2-enal
  参考文献：
  名称：

  Regioselective synthesis of fluoroaldols. Studies toward fluoroepothilones syntheses via antibody catalysis

  摘要：

  A general method for the synthesis of fluoromethyl aldols has been developed. Tributylboron enolates of fluoroacetone react with thiazole aldehydes (6) to provide fluoromethylaldols (4) regioselectively in high yields. Regioisomeric fluoroaldols (5) are produced as a 1:1 isomeric mixture of the erythro and three products via a two-step procedure: first, aldol reaction with Weinreb amide and then Grignard reaction. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01469-6

文献信息

• Sets of Aldolase Antibodies with Antipodal Reactivities. Formal Synthesis of Epothilone E by Large-Scale Antibody-Catalyzed Resolution of Thiazole Aldol
  作者：Subhash C. Sinha、Jian Sun、Gregory Miller、Carlos F. Barbas、Richard A. Lerner

  DOI：10.1021/ol990261h

  日期：1999.11.1

  Three monoclonal aldolase antibodies, generated against beta-diketone hapten by reactive immunization, catalyzed rapid and highly enantioselective retro-aldol reactions of ent-8a-k, providing optically pure 8a-k by kinetic resolution. Compounds (+/-)-8a, (+/-)-8g, and (+/-) 8k have been resolved in multigram quantities using 0,003, 0.005, and 0.0004 mol % antibody catalysts, respectively. Resolved compounds 8a-k are useful synthons for the construction of epothilones A-E (2-6) and their analogues. Here, a formal synthesis of epothilone E, 6 has been achieved starting from compound 8g.
• Regioselective synthesis of fluoroaldols. Studies toward fluoroepothilones syntheses via antibody catalysis
  作者：Subhash C. Sinha、Shantanu Dutta、Jian Sun

  DOI：10.1016/s0040-4039(00)01469-6

  日期：2000.10

  A general method for the synthesis of fluoromethyl aldols has been developed. Tributylboron enolates of fluoroacetone react with thiazole aldehydes (6) to provide fluoromethylaldols (4) regioselectively in high yields. Regioisomeric fluoroaldols (5) are produced as a 1:1 isomeric mixture of the erythro and three products via a two-step procedure: first, aldol reaction with Weinreb amide and then Grignard reaction. (C) 2000 Published by Elsevier Science Ltd.