1-[(1R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-1,3,3-trimethyl-2-methylidenecyclohexyl]-3-diazobutan-2-one | 302840-50-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[(1R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-1,3,3-trimethyl-2-methylidenecyclohexyl]-3-diazobutan-2-one
• CAS: 302840-50-2
• 化学式: C₂₀H₃₆N₂O₂Si
• 分子量: 364.604
• InChiKey: BXWHMQCEYDSHOP-YLJYHZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(1R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-1,3,3-trimethyl-2-methylidenecyclohexyl]-3-diazobutan-2-one 在 铜 、 copper(II) sulfate potassium tert-butylate 、 四丁基氟化铵 、 氨 、 lithium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 叔丁醇 、 苯 为溶剂， 反应 41.0h， 生成 (1R,2R,6S)-1,5,5,6,7,8-hexamethylbicyclo[4.3.0]non-7-en-2-ol
  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 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 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 80.67h， 生成 1-[(1R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-1,3,3-trimethyl-2-methylidenecyclohexyl]-3-diazobutan-2-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.