ethyl (4R)-2-isopropyl-4,5-dihydro-1,3-thiazole-4-carboxylate | 521317-04-4

• 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
• 英文名称: ethyl (4R)-2-isopropyl-4,5-dihydro-1,3-thiazole-4-carboxylate
• 英文别名: ethyl (4R)-2-propan-2-yl-4,5-dihydro-1,3-thiazole-4-carboxylate
• CAS: 521317-04-4
• 化学式: C₉H₁₅NO₂S
• 分子量: 201.29
• InChiKey: WOHUSHIMZDFCEO-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (4R)-2-isopropyl-4,5-dihydro-1,3-thiazole-4-carboxylate 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到2-异丙基噻唑-4-羧酸乙酯
  参考文献：
  名称：

  Total Synthesis of (+)-Cystothiazole A

  摘要：

  The total synthesis of cystothiazole A is described. Key steps of the synthesis include an Evans asymmetric catalytic aldol reaction, which established the required C-4-C-5 stereochemistry. The [2,4']-bis(thiazole) was obtained applying our methodology of electrophilic activation of amide. Semistabilized Wittig reaction between the phosphonium salt 3 and the aldehyde 2 afforded 1 in nine linear steps and 38% overall yield.

  DOI：

  10.1021/ol035600s
• 作为产物：
  描述：

  N,2-二甲基丙酰胺 、 L-半胱氨酸乙酯盐酸盐 在 吡啶 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到ethyl (4R)-2-isopropyl-4,5-dihydro-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Total Synthesis of (+)-Cystothiazole A

  摘要：

  The total synthesis of cystothiazole A is described. Key steps of the synthesis include an Evans asymmetric catalytic aldol reaction, which established the required C-4-C-5 stereochemistry. The [2,4']-bis(thiazole) was obtained applying our methodology of electrophilic activation of amide. Semistabilized Wittig reaction between the phosphonium salt 3 and the aldehyde 2 afforded 1 in nine linear steps and 38% overall yield.

  DOI：

  10.1021/ol035600s

文献信息

• Total Synthesis of (+)-Cystothiazole A
  作者：Patrick L. DeRoy、André B. Charette

  DOI：10.1021/ol035600s

  日期：2003.10.1

  The total synthesis of cystothiazole A is described. Key steps of the synthesis include an Evans asymmetric catalytic aldol reaction, which established the required C-4-C-5 stereochemistry. The [2,4']-bis(thiazole) was obtained applying our methodology of electrophilic activation of amide. Semistabilized Wittig reaction between the phosphonium salt 3 and the aldehyde 2 afforded 1 in nine linear steps and 38% overall yield.