(1R*,6S*)-6,9-dimethylbicyclo[4.3.0]non-8-en-3-one | 87995-01-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R*,6S*)-6,9-dimethylbicyclo[4.3.0]non-8-en-3-one
• 英文别名: cis-6,9-dimethylbicyclo[4.3.0]non-8-en-3-one；(3aS,7aS)-3,7a-dimethyl-3a,4,6,7-tetrahydro-1H-inden-5-one
• CAS: 87995-01-5
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: YBKMQBXVLLUDHU-GHMZBOCLSA-N

物化性质

• 沸点：
  239.1±9.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-((Z)-3-iodobut-2-en-1-yl)-3-isobutoxy-6-methylcyclohex-2-en-1-one 在 三甲基氯硅烷 、 水 、 叔丁基锂 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 Petroleum ether 、 正戊烷 为溶剂， 反应 1.83h， 生成 (1R*,6S*)-6,9-dimethylbicyclo[4.3.0]non-8-en-3-one
  参考文献：
  名称：

  Intramolecular Conjugate Addition of Alkenyl and Aryl Functions to Enones Initiated by Lithium−Iodine Exchange

  摘要：

  [GRAPHICS]Treatment of each of the substrates 20-26, 29, and 46-48 with t-BuLi in THF, in the presence of HMPA and TMSCl, provides good-to-excel lent yields of the intramolecular conjugate addition products 30-36, 37, and 49-51, respectively.

  DOI：

  10.1021/ol016288u

文献信息

• The synthesis of fused and bridged ring systems by free radical carbocyclization. A general route to masked 1,4-diketones.
  作者：N.N. Marinovic、H. Ramanathan

  DOI：10.1016/s0040-4039(00)81793-1

  日期：1983.1

  A new method for the synthesis of fused and bridged ring systems based on intramolecular addition of a vinyl radical to α,β-unsaturated carbonyls is described. The method represents a general route to masked γ-diketones.

  描述了一种新的合成稠合和桥环系统的方法，该方法基于将乙烯基自由基分子内加成到α，β-不饱和羰基上。该方法代表了掩蔽的γ-二酮的一般路线。
• Cu(I)-Mediated Intramolecular Conjugate Addition of Alkenyltrimethylstannane Functions to α,β-Unsaturated Ketones: A Convenient Preparation of Functionalized cis-Fused Bicyclo[4.3.0]non-8-en-3-ones and Bicyclo[3.3.0]oct-6-en-3-ones
  作者：E Piers

  DOI：10.1016/s0040-4020(00)00131-9

  日期：2000.4.28

  A new copper(I)-mediated method for effecting intramolecular conjugate addition of alkenyl functions to α,β-unsaturated ketone systems is reported. Treatment of the substrates 14, 15, 19–21, 22 and 23 with 2.5 equiv. of CuCl in DMF at room temperature affords excellent yields of the corresponding bicyclic ketones 24, 25, 29–31, 32 and 33. On the other hand, treatment of substances 15–18 with CuCN in

  报道了一种新的铜（I）介导的方法，用于将烯基官能团分子内共轭加成到α，β-不饱和酮系统上。所述基底的处理14，15，19 - 21，22和23与2.5当量。的CuCl在DMF中，在室温下的得到相应的双环酮的优异的产率24，25，29 - 31，32和33。另一方面，物质15 – 18的处理在60°C的DMSO中与CuCN一起使用可提供相应双环产物25 – 28的良好至优异的收率。
• Intramolecular Michael Additions: Copper(I) Chloride-Mediated Conjugate Addition of Vinyltrimethylstannane Functions to .alpha.,.beta.-Unsaturated Ketones
  作者：Edward Piers、Ernest J. McEachern、Patricia A. Burns

  DOI：10.1021/jo00113a006

  日期：1995.4
• Intramolecular Conjugate Addition of Alkenyl and Aryl Functions to Enones Initiated by Lithium−Iodine Exchange
  作者：Edward Piers、Cristian L. Harrison、Carlos Zetina-Rocha

  DOI：10.1021/ol016288u

  日期：2001.10.1

  [GRAPHICS]Treatment of each of the substrates 20-26, 29, and 46-48 with t-BuLi in THF, in the presence of HMPA and TMSCl, provides good-to-excel lent yields of the intramolecular conjugate addition products 30-36, 37, and 49-51, respectively.