methyl (1''E,5E,7E)-7-<6'-<3''-(tert-butyldimethylsiloxy)-1''-octenyl>-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene>heptenoate | 133230-29-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (1''E,5E,7E)-7-<6'-<3''-(tert-butyldimethylsiloxy)-1''-octenyl>-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene>heptenoate
• 英文别名: methyl (1''E,5E,7E)-7-{6'-[3''-(tert-butyldimethylsiloxy)-1''-octenyl]-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene}heptenoate
• CAS: 133230-29-2；133230-30-5
• 化学式: C₃₀H₅₀O₆Si
• 分子量: 534.809
• InChiKey: LBHNCHRLKGPCFX-UXBAJUCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl (1''E,5E,7E)-7-<6'-<3''-(tert-butyldimethylsiloxy)-1''-octenyl>-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene>heptenoate 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 作用下， 生成 methyl (1"E,6E)-7-<6'-(3"-acetoxy-1"-octenyl)-2',2'-dimethyl-3'aβ,6'aβ-dihydro-4'H-cyclopenta-1',3'-dioxol-5'-yl>-6-heptenoate 、 methyl (5E,7E,1"E)-7-<6'-(3"-acetoxy-1"-octenyl)-4'-oxo-2',2'-dimethyl-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene>-5-heptenoate
  参考文献：
  名称：

  Synthesis of PGE1 and various 10.alpha.-hydroxyprostaglandins

  摘要：

  Methods for the selective deprotection and/or reduction of compounds of type 2 to provide (7E)-7,8-di-dehydro-10-alpha-hydroxy-PGE1, (7E)-7,8-didehydro-10-alpha-hydroxy-PGF1, 10-alpha-hydroxy-PGF1, 10-alpha-hydroxy-PGF1, PGE1, and 15-epi-PGE1 as their racemic methyl esters have been examined.

  DOI：

  10.1021/jo00010a032
• 作为产物：
  描述：

  (E)-methyl 7-oxo-hept-5-enoate 、 (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 、 3-[(tert-butyldimethylsilyl)oxy]-1-(tributhylstannyl)-1(E)-octene 生成 methyl (1''E,5E,7E)-7-<6'-<3''-(tert-butyldimethylsiloxy)-1''-octenyl>-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene>heptenoate
  参考文献：
  名称：

  Development of a triply convergent aldol approach to prostanoids

  摘要：

  Various organocopper-mediated methods for the conjugate addition of alkyl and alkenyl groups to enone 1 to provide cyclopentanones 4 were studied. A variety of aldol-based procedures for the production of ketones 3 was evaluated, including a two-pot procedure involving generation of lithium enolates from 4, one-pot conjugate additions/aldol condensations methods, and methods involving the intermediate production of silyl enol ethers. The most promising procedure was found to be that involving trapping of the initial enolates from 1 as enol acetates and regeneration of enolates with methyllithium followed by aldol and dehydration reactions.

  DOI：

  10.1021/jo00010a031