(1Z,6E)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3,7,11-trimethyl-dodeca-1,6,10-trien-3-ol | 188957-33-7

• 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: (1Z,6E)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3,7,11-trimethyl-dodeca-1,6,10-trien-3-ol
• CAS: 188957-33-7
• 化学式: C₂₇H₄₄O₂Si
• 分子量: 428.731
• InChiKey: IGXDIXBRMKKGBL-IMBYEGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.31
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1Z,6E)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3,7,11-trimethyl-dodeca-1,6,10-trien-3-ol 在 cesium fluoride 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以97%的产率得到3-[(1Z,6E)-3-hydroxy-3,7,11-trimethyldodeca-1,6,10-trienyl]phenol
  参考文献：
  名称：

  The synthesis of 8a-methoxy-2H,6H-chromen-6-ones and corresponding 2H-chromenes by a unique process utilising phenolic oxidation

  摘要：

  (Z)-1-Hydroxy-3-(3'-hydroxyphenyl)prop-2-enes undergo phenolic oxidation by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2H,6H-dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substituted-Delta(3,4)-chromenes, the overall process being a unique heterocyclic synthesis in which the heteroatom is not initially attached to a benzene ring, but is introduced from a side chain. Parallel oxidations using cis-1-hydroxy-3-(3'-hydroxyphenyl)prop-2,3-oxiranes have also been achieved despite the presence of the sensitive oxirane ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00008-2
• 作为产物：
  描述：

  6,10-十二碳二烯-1-炔-3-醇,3,7,11-三甲基-,(6E)- 在 二氯二茂钛 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Isobutylmagnesium chloride 、 二异丙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (1Z,6E)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3,7,11-trimethyl-dodeca-1,6,10-trien-3-ol
  参考文献：
  名称：

  The synthesis of 8a-methoxy-2H,6H-chromen-6-ones and corresponding 2H-chromenes by a unique process utilising phenolic oxidation

  摘要：

  (Z)-1-Hydroxy-3-(3'-hydroxyphenyl)prop-2-enes undergo phenolic oxidation by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2H,6H-dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substituted-Delta(3,4)-chromenes, the overall process being a unique heterocyclic synthesis in which the heteroatom is not initially attached to a benzene ring, but is introduced from a side chain. Parallel oxidations using cis-1-hydroxy-3-(3'-hydroxyphenyl)prop-2,3-oxiranes have also been achieved despite the presence of the sensitive oxirane ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00008-2

文献信息

• The synthesis of 8a-methoxy-2H,6H-chromen-6-ones and corresponding 2H-chromenes by a unique process utilising phenolic oxidation
  作者：Andrew Pelter、Amjad Hussain、Gareth Smith、Robert S Ward

  DOI：10.1016/s0040-4020(97)00008-2

  日期：1997.3

  (Z)-1-Hydroxy-3-(3'-hydroxyphenyl)prop-2-enes undergo phenolic oxidation by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2H,6H-dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substituted-Delta(3,4)-chromenes, the overall process being a unique heterocyclic synthesis in which the heteroatom is not initially attached to a benzene ring, but is introduced from a side chain. Parallel oxidations using cis-1-hydroxy-3-(3'-hydroxyphenyl)prop-2,3-oxiranes have also been achieved despite the presence of the sensitive oxirane ring. (C) 1997 Elsevier Science Ltd.