{(1R,2R)-2-[(2E,7E)-4-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-11-oxo-dodeca-2,7-dienyl]-1-methyl-5-methylene-cyclopentyl}-acetaldehyde | 220472-43-5

• 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,2R)-2-[(2E,7E)-4-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-11-oxo-dodeca-2,7-dienyl]-1-methyl-5-methylene-cyclopentyl}-acetaldehyde
• 英文别名: 2-[(1R,2R)-2-[(2E,7E)-4-[tert-butyl(diphenyl)silyl]oxy-3,7-dimethyl-11-oxododeca-2,7-dienyl]-1-methyl-5-methylidenecyclopentyl]acetaldehyde
• CAS: 220472-43-5
• 化学式: C₃₉H₅₄O₃Si
• 分子量: 598.941
• InChiKey: GCECYKCPWVTZBI-VPBKMMBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {(1R,2R)-2-[(2E,7E)-4-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-11-oxo-dodeca-2,7-dienyl]-1-methyl-5-methylene-cyclopentyl}-acetaldehyde 在 titanium(III) chloride 、 铜 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以54%的产率得到tert-Butyl-diphenyl-((5E,10E,14E)-(3aR,16aR)-6,10,14,16a-tetramethyl-1-methylene-1,2,3,3a,4,7,8,9,12,13,16,16a-dodecahydro-cyclopentacyclopentadecen-7-yloxy)-silane
  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：

  6-甲基-5-庚烯-2-酮 在 咪唑 、 2,3,5-三甲基吡啶 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 二苯并-18-冠醚-6 、 selenium(IV) oxide 、 草酰氯 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 二甲基亚砜 、 甲基磺酰氯 、 三乙胺 、 水杨酸 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 114.5h， 生成 {(1R,2R)-2-[(2E,7E)-4-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-11-oxo-dodeca-2,7-dienyl]-1-methyl-5-methylene-cyclopentyl}-acetaldehyde
  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.