di<2-(1R,4R)-1,7,7-trimethylbicyclo<2.2.1>hept-2-enyl>carbinol | 126035-89-0

• 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: di<2-(1R,4R)-1,7,7-trimethylbicyclo<2.2.1>hept-2-enyl>carbinol
• 英文别名: Bis(2-bornen-2-yl)methanol
• CAS: 126035-89-0
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: GQLIFIGUAVGMJC-HANNOOJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  di<2-(1R,4R)-1,7,7-trimethylbicyclo<2.2.1>hept-2-enyl>carbinol 在 potassium hydrogensulfate 作用下， 反应 3.0h， 生成 (1R,5R,8R,9R,11S)-1,5,14,14,15,15-hexamethylpentacyclo<9.2.1.15,8.02,10.04,9>pentadeca-3,Δ2,10-diene 、 (1R,5R,8R,9S,11S)-1,5,14,14,15,15-hexamethylpentacyclo<9.2.1.15,8.02,10.04,9>pentadeca-3,Δ2,10-diene
  参考文献：
  名称：

  On the structural features of the chiral organometallic Lewis-acid catalyst “(dibornacyclopentadienyl)zirconiumtrichloride”

  摘要：

  2-Bornenyllithium (3) was prepared from camphor by a variant of the Shapiro reaction and then reacted with 0.5 molar equivalents of ethylformate to give the dibornenylcarbinol 4. Subsequent acid-catalyzed cyclization of 4 yielded ''dibornacyclopentadiene'' as a mixture of two diastereoisomers; their deprotonation with n-butyllithium produced a single ''dibornacyclopentadienyllithium'' reagent (6). Reaction of 6 with MCl4 (M = Zr, Hf, Ti) gave the chiral organometallic Lewis-acids ''(diborna-CP)MCl3''. ''(+)-(Dibornacyclopentadienyl)zirconiumtrichloride'' (7a) was characterized by X-ray diffraction. The molecular structure of 7a provides a basis for discussing the stereochemical characteristics of the enantioselective arene hydroxyalkylation process catalyzed by the optically active organometallic Lewis-acid ''(dibornacyclopentadienyl)zirconiumtrichloride''.

  DOI：

  10.1016/0022-328x(93)86061-l
• 作为产物：
  描述：

  白樟油 在 盐酸 、 仲丁基锂 作用下， 以 乙腈 为溶剂， 反应 26.33h， 生成 di<2-(1R,4R)-1,7,7-trimethylbicyclo<2.2.1>hept-2-enyl>carbinol
  参考文献：
  名称：

  On the structural features of the chiral organometallic Lewis-acid catalyst “(dibornacyclopentadienyl)zirconiumtrichloride”

  摘要：

  2-Bornenyllithium (3) was prepared from camphor by a variant of the Shapiro reaction and then reacted with 0.5 molar equivalents of ethylformate to give the dibornenylcarbinol 4. Subsequent acid-catalyzed cyclization of 4 yielded ''dibornacyclopentadiene'' as a mixture of two diastereoisomers; their deprotonation with n-butyllithium produced a single ''dibornacyclopentadienyllithium'' reagent (6). Reaction of 6 with MCl4 (M = Zr, Hf, Ti) gave the chiral organometallic Lewis-acids ''(diborna-CP)MCl3''. ''(+)-(Dibornacyclopentadienyl)zirconiumtrichloride'' (7a) was characterized by X-ray diffraction. The molecular structure of 7a provides a basis for discussing the stereochemical characteristics of the enantioselective arene hydroxyalkylation process catalyzed by the optically active organometallic Lewis-acid ''(dibornacyclopentadienyl)zirconiumtrichloride''.

  DOI：

  10.1016/0022-328x(93)86061-l

文献信息

• Erker, Gerhard; Zeijden, Adolphus A. H. van der, Angewandte Chemie, 1990, vol. 102, # 5, p. 543 - 545
  作者：Erker, Gerhard、Zeijden, Adolphus A. H. van der

  DOI：——

  日期：——