(1R,3S,6R,7R)-7-(tert-butyldimethylsilyloxy)-3,6,10,10-tetramethyltricyclo[4.4.0.0^1,3]decan-4-one | 302840-51-3

• 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: (1R,3S,6R,7R)-7-(tert-butyldimethylsilyloxy)-3,6,10,10-tetramethyltricyclo[4.4.0.0^1,3]decan-4-one
• 英文别名: (1aS,3aR,4R,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-1a,3a,7,7-tetramethyl-3,4,5,6-tetrahydro-1H-cyclopropa[i]inden-2-one
• CAS: 302840-51-3
• 化学式: C₂₀H₃₆O₂Si
• 分子量: 336.59
• InChiKey: ADGALWSYULZBCU-XWPNQZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3S,6R,7R)-7-(tert-butyldimethylsilyloxy)-3,6,10,10-tetramethyltricyclo[4.4.0.0^1,3]decan-4-one 在 potassium tert-butylate 、 氨 、 lithium 作用下， 以 叔丁醇 、 苯 为溶剂， 反应 6.0h， 生成 (+)-thaps-8(11)-en-5-ol tert-butyldimethylsilyl ether
  参考文献：
  名称：

  An enantiospecific approach to thapsanes from R-carvone: synthesis of (−)-thaps-8-en-5-ol

  摘要：

  The first enantiospecific synthesis of a thapsane, containing three contiguous quaternary carbon atoms, is accomplished starting from R-carvone. An intramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo- and regiospecific generation of three contiguous quaternary carbon atoms present in the thapsane framework. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01107-2
• 作为产物：
  描述：

  (+)-methyl (1R)-1,5,5-trimethyl-6-methylenecyclohex-3-en-2-one-1-acetate 在 palladium on activated charcoal 、 铜 、 copper(II) sulfate 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 草酰氯 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 环己烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 85.67h， 生成 (1R,3S,6R,7R)-7-(tert-butyldimethylsilyloxy)-3,6,10,10-tetramethyltricyclo[4.4.0.0^1,3]decan-4-one
  参考文献：
  名称：

  An enantiospecific approach to thapsanes from R-carvone: synthesis of (−)-thaps-8-en-5-ol

  摘要：

  The first enantiospecific synthesis of a thapsane, containing three contiguous quaternary carbon atoms, is accomplished starting from R-carvone. An intramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo- and regiospecific generation of three contiguous quaternary carbon atoms present in the thapsane framework. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01107-2

文献信息

• Srikrishna; Anebouselvy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 3, p. 449 - 459
  作者：Srikrishna、Anebouselvy

  DOI：——

  日期：——
• An enantiospecific approach to thapsanes from R-carvone: synthesis of (−)-thaps-8-en-5-ol
  作者：A Srikrishna、K Anebouselvy、T.Jagadeeshwar Reddy

  DOI：10.1016/s0040-4039(00)01107-2

  日期：2000.8

  The first enantiospecific synthesis of a thapsane, containing three contiguous quaternary carbon atoms, is accomplished starting from R-carvone. An intramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo- and regiospecific generation of three contiguous quaternary carbon atoms present in the thapsane framework. (C) 2000 Published by Elsevier Science Ltd.