(E)-1-Bromo-15-(tert-butyldimethylsiloxy)-1-pentadecene | 152565-03-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-1-Bromo-15-(tert-butyldimethylsiloxy)-1-pentadecene
• 英文别名: [(E)-15-bromopentadec-14-enoxy]-tert-butyl-dimethylsilane
• CAS: 152565-03-2
• 化学式: C₂₁H₄₃BrOSi
• 分子量: 419.561
• InChiKey: YYPSAQMDISHOQO-HTXNQAPBSA-N

物化性质

• 沸点：
  412.7±18.0 °C(predicted)
• 密度：
  0.989±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-Bromo-15-(tert-butyldimethylsiloxy)-1-pentadecene 在 Pd 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 (E)-1-Methanesulfonyl-14-hexadecene
  参考文献：
  名称：

  Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita

  摘要：

  Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the beta-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.

  DOI：

  10.1021/jo00076a044
• 作为产物：
  描述：

  14-十五炔-1-醇 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 二氯二茂锆 、 三乙基硼氢化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.08h， 生成 (E)-1-Bromo-15-(tert-butyldimethylsiloxy)-1-pentadecene
  参考文献：
  名称：

  Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita

  摘要：

  Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the beta-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.

  DOI：

  10.1021/jo00076a044

文献信息

• Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita
  作者：Michael Miller、Louis S. Hegedus

  DOI：10.1021/jo00076a044

  日期：1993.11

  Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the beta-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.