(1R,2S,4R)-2-(4-ethynylphenyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol | 943154-11-8

• 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: (1R,2S,4R)-2-(4-ethynylphenyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 943154-11-8
• 化学式: C₁₈H₂₂O
• 分子量: 254.372
• InChiKey: KZBQOCZYHACUCI-NXHRZFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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,2S,4R)-2-(4-ethynylphenyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 在 carbon monoxide,cobalt,cyclopenta-1,3-diene 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (1R,2S,4R)-2-[4-[3,5-bis[4-[(1R,2S,4R)-2-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]phenyl]phenyl]phenyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 、 (1R,2S,4R)-2-[4-[3,4-bis[4-[(1R,2S,4R)-2-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]phenyl]phenyl]phenyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Synthesis of Terpene and Steroid Dimers and Trimers Having Cyclobutadienyl−Co and Aromatic Tethers

  摘要：

  The reaction of natural product derived propargylic alcohols with CpCo(CO)(2) produces three new types of natural product hybrids having two or three terpene or steroid fragments. The tether joining the natural product subunits is built during the reaction. Type 1 hybrids have two terpene or steroid moieties joined by a CpCo-cyclobutadiene tether, with the two units disposed in a 1,2-arrangement (9, 14, 22). Type 2 hybrids have a Co-cyclopentadienone tether (10). Type 3 has three units of terpene or steroid joined to a benzene ring (11, 12, 15). An unusual Co-mediated beta-carbon elimination pathway of propargylic alcohols leading to ketones (an unknown process in this chemistry) has been observed.

  DOI：

  10.1021/jo0703698
• 作为产物：
  描述：

  (4-溴苯基乙炔基)三甲基硅烷 在 四丁基氟化铵 、 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 9.67h， 生成 (1R,2S,4R)-2-(4-ethynylphenyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Synthesis of Terpene and Steroid Dimers and Trimers Having Cyclobutadienyl−Co and Aromatic Tethers

  摘要：

  The reaction of natural product derived propargylic alcohols with CpCo(CO)(2) produces three new types of natural product hybrids having two or three terpene or steroid fragments. The tether joining the natural product subunits is built during the reaction. Type 1 hybrids have two terpene or steroid moieties joined by a CpCo-cyclobutadiene tether, with the two units disposed in a 1,2-arrangement (9, 14, 22). Type 2 hybrids have a Co-cyclopentadienone tether (10). Type 3 has three units of terpene or steroid joined to a benzene ring (11, 12, 15). An unusual Co-mediated beta-carbon elimination pathway of propargylic alcohols leading to ketones (an unknown process in this chemistry) has been observed.

  DOI：

  10.1021/jo0703698