(1R,5S,6R)-2,2,5-trimethylbicyclo[3.2.0]hept-3-en-6-ol | 134525-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5S,6R)-2,2,5-trimethylbicyclo[3.2.0]hept-3-en-6-ol
• CAS: 134525-77-2
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: MSSBLPKWJJOUMD-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,5S,6R)-2,2,5-trimethylbicyclo[3.2.0]hept-3-en-6-ol 在 palladium on activated charcoal (COCl₂)2 、 氯化锑(V) 、 氢气 、 二甲基亚砜 、 sodium chloride 作用下， 生成 (3aR,6aS)-4,4,6a-Trimethyl-hexahydro-pentalen-1-one
  参考文献：
  名称：

  Synthesis of naturally-occurring (−)-Δ9(12)-Capnellene and its antipode: an application of the photo-induced vinylcyclopropane-cyclopentene rearrangement

  摘要：

  Abundantly available (+)-DELTA-3-Carene, 1 has been transformed into enantiomerically pure key intermediates viz. the enones (-)-7 and (+)-7, thus constituting a formal synthesis of both the enantiomers of DELTA-9(12)-Capnellene.

  DOI：

  10.1016/s0040-4039(00)74500-x
• 作为产物：
  描述：

  (+)-4α-acetoxy-2-carene 生成 (1R,5S,6R)-2,2,5-trimethylbicyclo[3.2.0]hept-3-en-6-ol
  参考文献：
  名称：

  Synthesis of naturally-occurring (−)-Δ9(12)-Capnellene and its antipode: an application of the photo-induced vinylcyclopropane-cyclopentene rearrangement

  摘要：

  Abundantly available (+)-DELTA-3-Carene, 1 has been transformed into enantiomerically pure key intermediates viz. the enones (-)-7 and (+)-7, thus constituting a formal synthesis of both the enantiomers of DELTA-9(12)-Capnellene.

  DOI：

  10.1016/s0040-4039(00)74500-x

文献信息

• A new methodology for the synthesis of bicyclo [3.2.0]heptenes from cis-methylvinylcyclopropanes
  作者：H.R. Sonawane、B.S. Nanjundiah、M. Udaya Kumar

  DOI：10.1016/s0040-4039(00)98522-8

  日期：1985.1

  A practical photolytic approach has been developed to furnish synthetically useful bicyclo[3.2.O]heptene derivatives from -methylvinylcyclopropanes; such products are not generally accessible by thermal processes owing to the competing retro-ene reaction.

  已经开发出一种实用的光解方法，以从-甲基乙烯基环丙烷提供合成上有用的双环[3.2.O]庚烯衍生物。由于竞争性逆向烯反应，这种产物通常不能通过热过程获得。
• Synthesis of naturally-occurring (−)-Δ9(12)-Capnellene and its antipode: an application of the photo-induced vinylcyclopropane-cyclopentene rearrangement
  作者：H.R. Sonawane、B.S. Nanjundiah、V.G. Shah、D.G. Kulkarni、Jaimala R. Ahuja

  DOI：10.1016/s0040-4039(00)74500-x

  日期：1991.2

  Abundantly available (+)-DELTA-3-Carene, 1 has been transformed into enantiomerically pure key intermediates viz. the enones (-)-7 and (+)-7, thus constituting a formal synthesis of both the enantiomers of DELTA-9(12)-Capnellene.