3-bromo-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-ene | 1263941-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-ene
• 英文别名: 3-Bromo-2-{(2s)-1,4-dioxaspiro[4.5]dec-2-yl}-prop-1-ene；(3S)-3-(3-bromoprop-1-en-2-yl)-1,4-dioxaspiro[4.5]decane
• CAS: 1263941-22-5
• 化学式: C₁₁H₁₇BrO₂
• 分子量: 261.159
• InChiKey: ONKNGQYMRHPWCC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-ene 在 吡啶 、 咪唑 、 盐酸 、 正丁基锂 、 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 26.0h， 生成 (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：

  1,2:5,6-二-O-亚环己基-D-甘露醇 在 titanium(IV) isopropylate 、 potassium metaperiodate 、 potassium hydrogencarbonate 、 三乙胺 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 水 为溶剂， 反应 8.0h， 生成 3-bromo-2-{(2S)-1,4-dioxaspiro[4.5]dec-2-yl}prop-1-ene
  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.