4-[(1E)-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-enyl]-2-methylthiazole | 1263941-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[(1E)-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-enyl]-2-methylthiazole
• 英文别名: 4-[(1e)-2-{(2s)-1,4-Dioxaspiro[4.5]dec-2-yl}-prop-1-en-1-yl]-2-methylthiazole；4-[(E)-2-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]prop-1-enyl]-2-methyl-1,3-thiazole
• CAS: 1263941-30-5
• 化学式: C₁₅H₂₁NO₂S
• 分子量: 279.403
• InChiKey: BIGAAEBQVFWMNG-BMGYJQCNSA-N

物化性质

• 沸点：
  419.4±35.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-(2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-2-enyl)-2-methylthiazole 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以94%的产率得到4-[(1E)-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-enyl]-2-methylthiazole
  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