(2E,6E)-9-((1S)-2,2-dimethyl-6-methylenecyclohexyl)-3,7-dimethyl-1-(tetrahydro-2-pyranyl)oxy-2,6-nonadiene | 502763-37-3

• 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: (2E,6E)-9-((1S)-2,2-dimethyl-6-methylenecyclohexyl)-3,7-dimethyl-1-(tetrahydro-2-pyranyl)oxy-2,6-nonadiene
• 英文别名: 2-[(2E,6E)-9-[(1S)-2,2-dimethyl-6-methylene-cyclohexyl]-3,7-dimethyl-nona-2,6-dienoxy]tetrahydropyran；2-[(2E,6E)-9-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-3,7-dimethylnona-2,6-dienoxy]oxane
• CAS: 502763-37-3
• 化学式: C₂₅H₄₂O₂
• 分子量: 374.607
• InChiKey: WMNSQAUGWYYHAJ-IBFWGRKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,6E)-9-((1S)-2,2-dimethyl-6-methylenecyclohexyl)-3,7-dimethyl-1-(tetrahydro-2-pyranyl)oxy-2,6-nonadiene 在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以100%的产率得到(E)-6-hydroxy-4-methyl-4-hexenal tetrahydropyranyl ether
  参考文献：
  名称：

  Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P

  摘要：

  Lipase-catalyzed kinetic resolution of gamma-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-gamma-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-gamma-cyclogeraniol, and the absolute configuration of natural (+)-luffarin-P was determined to have an S configuration by our first synthesis of (S)-luffarin-P for the first time. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.11.019
• 作为产物：
  描述：

  (S)-(-)-2,2-dimethyl-6-methylene-1-[1'-(phenylthio)methyl]cyclohexane 在 正丁基锂 、 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 42.0h， 生成 (2E,6E)-9-((1S)-2,2-dimethyl-6-methylenecyclohexyl)-3,7-dimethyl-1-(tetrahydro-2-pyranyl)oxy-2,6-nonadiene
  参考文献：
  名称：

  Synthesis of (+)-trixagol and its enantiomer, the terpenoid side chain of (−)-agelasine E

  摘要：

  The naturally occurring gamma-cyclogeranylgeraniol called (+)-trixagol has been synthesised for the first time. Trixagol was readily available in five steps from (S)-2,2-dimethyl-6-methylene-1-cyclohexanemethanol. The enantiomer of trixagol, which equates to the terpenoid side chain of the naturally occurring 7,9-dialkylpurinium salt (-)-agelasine E, was prepared from the (R) enantiomer of the cyclohexanemethanol. Both trixagol enantiomers were moderately active against Mycobacterium tuberculosis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01455-2

文献信息

• Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P
  作者：Mikio Fujii、Yosuke Morimoto、Machiko Ono、Hiroyuki Akita

  DOI：10.1016/j.molcatb.2015.11.019

  日期：2016.1

  Lipase-catalyzed kinetic resolution of gamma-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-gamma-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-gamma-cyclogeraniol, and the absolute configuration of natural (+)-luffarin-P was determined to have an S configuration by our first synthesis of (S)-luffarin-P for the first time. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis of (+)-trixagol and its enantiomer, the terpenoid side chain of (−)-agelasine E
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen

  DOI：10.1016/s0040-4020(02)01455-2

  日期：2003.1

  The naturally occurring gamma-cyclogeranylgeraniol called (+)-trixagol has been synthesised for the first time. Trixagol was readily available in five steps from (S)-2,2-dimethyl-6-methylene-1-cyclohexanemethanol. The enantiomer of trixagol, which equates to the terpenoid side chain of the naturally occurring 7,9-dialkylpurinium salt (-)-agelasine E, was prepared from the (R) enantiomer of the cyclohexanemethanol. Both trixagol enantiomers were moderately active against Mycobacterium tuberculosis. (C) 2002 Elsevier Science Ltd. All rights reserved.