7-Methyl-trans-bicyclo<4.3.0>nonane | 19744-66-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 7-Methyl-trans-bicyclo<4.3.0>nonane
• 英文别名: 7-Methyl-trans-bicyclo[4.3.0]nonane；(3aR,7aR)-1-methyl-2,3,3a,4,5,6,7,7a-octahydro-1H-indene
• CAS: 19744-66-2；28436-03-5；28436-04-6；53927-25-6；53927-26-7
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: NOIDOYJLIPVSOK-VXRWAFEHSA-N

物化性质

• 沸点：
  91-93 °C(Press: 17 Torr)
• 密度：
  0.8722 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  2,3-二氢-1H-茚-1-甲醇 在 Rh on carbon 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 生成 cis perhydro-1-methylindane 、 7-Methyl-trans-bicyclo<4.3.0>nonane 、 [(1R,3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-inden-1-yl]methanol 、
  参考文献：
  名称：

  Functional-Group-Directed Diastereoselective Hydrogenation of Aromatic Compounds. 1

  摘要：

  Diastereoselective liquid phase hydrogenation of a series of monosubstituted indane and tetralin substrates was studied on supported rhodium catalysts. Predominantly the cis-cis diastereomer, obtained by hydrogenation from the diastereoface opposite the substituent (at the stereogenic center), and the cis-trans diastereomer, obtained by hydrogenation from the diastereoface on the same side as the substituent, were formed. The diastereoselectivity between the two isomers was dependent on the steric repulsion or the electronic attraction of the substituent with the surface of the catalyst. The hydroxyl group did not exhibit a strong attraction (haptophilicity), and the cis-cis diastereomer was obtained as the major product. The amino group exhibited a very high haptophilicity, yielding primarily the cis-trans diastereomer. The diastereoselectivity obtained in the hydrogenation of all the substrates was influenced on addition of bases to the reaction mixture. In the case of alcoholic substrates, the selectivity to the cis-trans diastereomer could be substantially increased with alkaline hydroxide additives.

  DOI：

  10.1021/jo991091p

文献信息

• Mach, Karel; Petrusova, Lidmila; Antropiusova, Helena, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 10, p. 2924 - 2936
  作者：Mach, Karel、Petrusova, Lidmila、Antropiusova, Helena、Hanus, Vladimir、Turecek, Frantisek、Sedmera, Petr

  DOI：——

  日期：——