(3R,4aS,5R)-4a,5-dimethyl-3-(1,1,3,3,3-pentadeuterioprop-1-en-2-yl)-2,3,4,5,6,7-hexahydro-1H-naphthalene | 1174496-34-4

• 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: (3R,4aS,5R)-4a,5-dimethyl-3-(1,1,3,3,3-pentadeuterioprop-1-en-2-yl)-2,3,4,5,6,7-hexahydro-1H-naphthalene
• CAS: 1174496-34-4
• 化学式: C₁₅H₂₄
• 分子量: 209.316
• InChiKey: QEBNYNLSCGVZOH-SAZIGHKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  巴伦西亚橘烯 在 C₂₁H₃₅N₃PRu*F₆P^(1-) 、 重水 作用下， 以 氘代丙酮 为溶剂， 反应 120.0h， 生成 (3R,4aS,5R)-4a,5-dimethyl-3-(1,1,3,3,3-pentadeuterioprop-1-en-2-yl)-2,3,4,5,6,7-hexahydro-1H-naphthalene
  参考文献：
  名称：

  Mild and Selective Deuteration and Isomerization of Alkenes by a Bifunctional Catalyst and Deuterium Oxide

  摘要：

  H/D exchange is achieved at allylic positions of alkenes using D2O in acetone and alkene isomerization catalyst 1, which features a bifunctional imidazolylphosphine. The basic nitrogen of the latter is thought to deprotonate an alkene substrate coordinated to the CpRu center; at this stage the protonated nitrogen could undergo H/D exchange with deuterium oxide. An exceptional degree of deuteration is achieved at positions accessible to isomerization, with a high degree of control. Using biphasic settings one can literally wash out reactive protons on the substrate without using organic solvents.

  DOI：

  10.1021/ja903519a

文献信息

• Mild and Selective Deuteration and Isomerization of Alkenes by a Bifunctional Catalyst and Deuterium Oxide
  作者：Gülin Erdogan、Douglas B. Grotjahn

  DOI：10.1021/ja903519a

  日期：2009.8.5

  H/D exchange is achieved at allylic positions of alkenes using D2O in acetone and alkene isomerization catalyst 1, which features a bifunctional imidazolylphosphine. The basic nitrogen of the latter is thought to deprotonate an alkene substrate coordinated to the CpRu center; at this stage the protonated nitrogen could undergo H/D exchange with deuterium oxide. An exceptional degree of deuteration is achieved at positions accessible to isomerization, with a high degree of control. Using biphasic settings one can literally wash out reactive protons on the substrate without using organic solvents.