cis-8-hydroxycalamenene | 80850-84-6

• 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: cis-8-hydroxycalamenene
• 英文别名: (5R,8R)-3,8-dimethyl-5-propan-2-yl-5,6,7,8-tetrahydronaphthalen-1-ol
• CAS: 80850-84-6；88642-92-6；95908-34-2；96646-99-0；96647-00-6；115795-61-4；136033-37-9
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: FDMKIGKOMRSCAW-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  cis-8-hydroxycalamenene 在 氨 、 lithium 、 sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1,6-二甲基-4-丙烷-2-基-1,2,3,4-四氢萘
  参考文献：
  名称：

  Aromatic annulation on the p-menthane monoterpenes: enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene

  摘要：

  A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.037
• 作为产物：
  描述：

  2,15-dihydroxycalamenene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 cis-8-hydroxycalamenene
  参考文献：
  名称：

  Aromatic annulation on the p-menthane monoterpenes: enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene

  摘要：

  A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.037

文献信息

• STEREO- AND REGIOSELECTIVE SYNTHESIS OF HYDROXYCALAMENENES VIA (ARENE)TRICARBONYL CHROMIUM COMPLEXES
  作者：Motokazu Uemura、Kazuo Isobe、Yuji Hayashi

  DOI：10.1246/cl.1985.91

  日期：1985.1.5

  Stereoisomers of 7- and 8-hydroxycalamenenes were synthesized stereo- and regioselectively via (arene)tricarbony1 chromium complexes.

  通过（芳烃）三羰基铬配合物立体选择性地和区域选择性地合成了 7-和 8-羟基葫芦烯的立体异构体。
• TANAKA, JUICHI;NOBUTANI, KIMIAKI;ADACHI, KAZUO, NIPPON KAGAKU KAJSI,(1988) N 7, S. 1065-1073
  作者：TANAKA, JUICHI、NOBUTANI, KIMIAKI、ADACHI, KAZUO

  DOI：——

  日期：——
• Aromatic annulation on the p-menthane monoterpenes: enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene
  作者：Stefano Serra、Claudio Fuganti

  DOI：10.1016/j.tetlet.2005.05.037

  日期：2005.7

  A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively. (c) 2005 Elsevier Ltd. All rights reserved.