(3S,4E)-3-hydroxy-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enenitrile | 1263941-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3S,4E)-3-hydroxy-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enenitrile
• 英文别名: (E,3R)-3-hydroxy-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-enenitrile
• CAS: 1263941-38-3
• 化学式: C₁₀H₁₂N₂OS
• 分子量: 208.284
• InChiKey: JQTHLNUIQRYNOI-BREXMAIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4E)-3-hydroxy-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enenitrile 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以94%的产率得到(3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enenitrile
  参考文献：
  名称：

  Synthesis of epothilones molecule fragment (15R)-C 13 -C 21 from D-mannitol

  摘要：

  Efficient synthesis of an epothilone molecules fragment (15R)-C-13-C-21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide and the transformation of the obtained cyclopropanol into the corresponding 2-substituted allyl bromide. The coupling of the latter catalyzed by copper with 2-methylthiazolyl-4-magnesium bromide, the shift of a double carbon-carbon bond in the product obtained into the position, conjugated with the thiazole ring, and the common transformation of the protected 1,2-diol function afforded the target compound in 15% yield.

  DOI：

  10.1134/s1070428010110175
• 作为产物：
  描述：

  4-[(1E)-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-enyl]-2-methylthiazole 在 吡啶 、 盐酸 、 水 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 19.0h， 生成 (3S,4E)-3-hydroxy-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enenitrile
  参考文献：
  名称：

  Synthesis of epothilones molecule fragment (15R)-C 13 -C 21 from D-mannitol

  摘要：

  Efficient synthesis of an epothilone molecules fragment (15R)-C-13-C-21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide and the transformation of the obtained cyclopropanol into the corresponding 2-substituted allyl bromide. The coupling of the latter catalyzed by copper with 2-methylthiazolyl-4-magnesium bromide, the shift of a double carbon-carbon bond in the product obtained into the position, conjugated with the thiazole ring, and the common transformation of the protected 1,2-diol function afforded the target compound in 15% yield.

  DOI：

  10.1134/s1070428010110175

文献信息

• Synthesis of epothilones molecule fragment (15R)-C 13 -C 21 from D-mannitol
  作者：V. N. Kovalenko、N. A. Sokolov、O. G. Kulinkovich

  DOI：10.1134/s1070428010110175

  日期：2010.11

  Efficient synthesis of an epothilone molecules fragment (15R)-C-13-C-21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide and the transformation of the obtained cyclopropanol into the corresponding 2-substituted allyl bromide. The coupling of the latter catalyzed by copper with 2-methylthiazolyl-4-magnesium bromide, the shift of a double carbon-carbon bond in the product obtained into the position, conjugated with the thiazole ring, and the common transformation of the protected 1,2-diol function afforded the target compound in 15% yield.