(4R,4aR)-4-(Diethylamino-diphenyl-silanyl)-4a-((S)-5,5-dimethyl-2-oxo-[1,3]dioxolan-4-ylmethyl)-8-isobutyryl-7,7-dimethyl-3,4,4a,5,6,7-hexahydro-chromen-2-one | 1027909-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (4R,4aR)-4-(Diethylamino-diphenyl-silanyl)-4a-((S)-5,5-dimethyl-2-oxo-[1,3]dioxolan-4-ylmethyl)-8-isobutyryl-7,7-dimethyl-3,4,4a,5,6,7-hexahydro-chromen-2-one
• 英文别名: (4R,4aR)-4-[diethylamino(diphenyl)silyl]-4a-[[(4S)-5,5-dimethyl-2-oxo-1,3-dioxolan-4-yl]methyl]-7,7-dimethyl-8-(2-methylpropanoyl)-3,4,5,6-tetrahydrochromen-2-one
• CAS: 1027909-19-8
• 化学式: C₃₇H₄₉NO₆Si
• 分子量: 631.885
• InChiKey: FSKRQRLUNJLSQM-UOZVSXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,4aR)-4-(Diethylamino-diphenyl-silanyl)-4a-((S)-5,5-dimethyl-2-oxo-[1,3]dioxolan-4-ylmethyl)-8-isobutyryl-7,7-dimethyl-3,4,4a,5,6,7-hexahydro-chromen-2-one 在 palladium on activated charcoal 2,6-二甲基吡啶 、 三乙基硅烷 、 potassium fluoride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-3-[(S)-1-((S)-5,5-Dimethyl-2-oxo-[1,3]dioxolan-4-ylmethyl)-3-isobutyryl-4,4-dimethyl-2-oxo-cyclohexyl]-3-triethylsilanyloxy-propionaldehyde
  参考文献：
  名称：

  Studies toward the total synthesis of garsubellin A: synthesis of 8-deprenyl-garsubellin A

  摘要：

  During studies directed toward the total synthesis of garsubellin A, synthesis of 8-deprenyl-garsubellin A, containing three (of four in the natural product) stereocenters with the proper configurations, was achieved. Key steps are a one-pot lactone formation, a formal migration to the bicyclo[3.3.1]nonane-1,3,5-trione, and an intramolecular Wacker-type tetrahydrofuran formation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00650-0
• 作为产物：
  描述：

  5-{(1R,3R)-3-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-4,4-dimethyl-2-oxo-cyclohexylmethyl}-4,4-dimethyl-[1,3]dioxolan-2-one 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 (4R,4aR)-4-(Diethylamino-diphenyl-silanyl)-4a-((S)-5,5-dimethyl-2-oxo-[1,3]dioxolan-4-ylmethyl)-8-isobutyryl-7,7-dimethyl-3,4,4a,5,6,7-hexahydro-chromen-2-one
  参考文献：
  名称：

  Studies toward the total synthesis of garsubellin A: synthesis of 8-deprenyl-garsubellin A

  摘要：

  During studies directed toward the total synthesis of garsubellin A, synthesis of 8-deprenyl-garsubellin A, containing three (of four in the natural product) stereocenters with the proper configurations, was achieved. Key steps are a one-pot lactone formation, a formal migration to the bicyclo[3.3.1]nonane-1,3,5-trione, and an intramolecular Wacker-type tetrahydrofuran formation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00650-0