2,15-dihydroxycalamenene | 874657-05-3

• 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: 2,15-dihydroxycalamenene
• 英文别名: (5R,8R)-3-(hydroxymethyl)-8-methyl-5-propan-2-yl-5,6,7,8-tetrahydronaphthalen-1-ol
• CAS: 874657-05-3
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: ZCURUYBTMVDZFO-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  cis-menthonetosylhydrazone 在 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.84h， 生成 2,15-dihydroxycalamenene
  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

• 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.

表征谱图