1-[(1S,2S,3R,5R,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-yl]-3-methyl-but-3-en-1-one | 148903-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1-[(1S,2S,3R,5R,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-yl]-3-methyl-but-3-en-1-one
• 英文别名: 1-[(1S,2S,3R,5R,6R)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-7-oxabicyclo[4.1.0]heptan-3-yl]-3-methylbut-3-en-1-one
• CAS: 148903-11-1
• 化学式: C₂₃H₄₄O₄Si₂
• 分子量: 440.771
• InChiKey: FUODDZUJRJBODM-DARKYYSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(1S,2S,3R,5R,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-yl]-3-methyl-but-3-en-1-one 在 敌草腈 、 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (+)-eutipoxide B
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Eutypoxide B

  摘要：

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.

  DOI：

  10.1021/jo9617326
• 作为产物：
  描述：

  1-[(1S,2S,3S,5R,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-yl]-3-methyl-but-3-en-1-ol 在 戴斯-马丁氧化剂 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到1-[(1S,2S,3R,5R,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-yl]-3-methyl-but-3-en-1-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Eutypoxide B

  摘要：

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.

  DOI：

  10.1021/jo9617326

文献信息

• Enantioselective Total Synthesis of (+)-Eutypoxide B
  作者：M. Teresa Barros、Christopher D. Maycock、M. Rita Ventura

  DOI：10.1021/jo9617326

  日期：1997.6.13

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.