2-[(1R,2R)-2-(bromomethyl)-2-methyl-3-methylidenecyclopentyl]ethoxymethylbenzene | 220466-90-0

• 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: 2-[(1R,2R)-2-(bromomethyl)-2-methyl-3-methylidenecyclopentyl]ethoxymethylbenzene
• CAS: 220466-90-0
• 化学式: C₁₇H₂₃BrO
• 分子量: 323.273
• InChiKey: RRHHDEVVHZXWIG-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(1R,2R)-2-(bromomethyl)-2-methyl-3-methylidenecyclopentyl]ethoxymethylbenzene 在 咪唑 、 lithium aluminium tetrahydride 、 二苯并-18-冠醚-6 、 草酰氯 、 oxonium 、 lithium 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 乙胺 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 67.0h， 生成 (2E,7E)-3,7-Dimethyl-1-[(1R,2R)-2-methyl-3-methylene-2-(2-triisopropylsilanyloxy-ethyl)-cyclopentyl]-11-triisopropylsilanyloxy-dodeca-2,7-dien-4-ol
  参考文献：
  名称：

  A synthesis of the ring system of terpestacin

  摘要：

  The ring system of the sesterterpene terpestacin has been obtained from a cyclopentanic precursor prepared from endo-3-bromocamphor and from an acyclic keto phosphonate prepared from 6-methylhept-5-en-2-one. The connection of both compounds has been achieved by a Horner-Wadsworth-Emmons reaction on the one hand and by a McMurry reaction on the other. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02535-0
• 作为产物：
  描述：

  (1R,2R)-2-Bromomethyl-1-methoxycarbonylmethyl-2-methyl-3-methylenecyclopentane 在 lithium aluminium tetrahydride 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 2-[(1R,2R)-2-(bromomethyl)-2-methyl-3-methylidenecyclopentyl]ethoxymethylbenzene
  参考文献：
  名称：

  A synthesis of the ring system of terpestacin

  摘要：

  The ring system of the sesterterpene terpestacin has been obtained from a cyclopentanic precursor prepared from endo-3-bromocamphor and from an acyclic keto phosphonate prepared from 6-methylhept-5-en-2-one. The connection of both compounds has been achieved by a Horner-Wadsworth-Emmons reaction on the one hand and by a McMurry reaction on the other. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02535-0

文献信息

• A synthesis of the ring system of terpestacin
  作者：Marie-Paule Mermet-Mouttet、Kiroubagaranne Gabriel、Denis Heissler

  DOI：10.1016/s0040-4039(98)02535-0

  日期：1999.1

  The ring system of the sesterterpene terpestacin has been obtained from a cyclopentanic precursor prepared from endo-3-bromocamphor and from an acyclic keto phosphonate prepared from 6-methylhept-5-en-2-one. The connection of both compounds has been achieved by a Horner-Wadsworth-Emmons reaction on the one hand and by a McMurry reaction on the other. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.