(3R,4R,E)-2-(((2R,3R)-3-(4-((tert-butyldimethylsilyl)oxy)butyl)oxiran-2-yl)methylene)-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone | 1605291-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R,E)-2-(((2R,3R)-3-(4-((tert-butyldimethylsilyl)oxy)butyl)oxiran-2-yl)methylene)-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone
• 英文别名: (2E,3R,4R)-2-[[(2R,3R)-3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]oxiran-2-yl]methylidene]-4-[(4-methoxyphenyl)methoxy]-3-oct-2-ynylcyclopentan-1-one
• CAS: 1605291-97-1
• 化学式: C₃₄H₅₂O₅Si
• 分子量: 568.869
• InChiKey: NKUCTUMSPSQTMI-UXBRCCOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.03
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,E)-2-(((2R,3R)-3-(4-((tert-butyldimethylsilyl)oxy)butyl)oxiran-2-yl)methylene)-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone 在 sodium chlorite 、 sodium dihydrogenphosphate 、 甲酸 、 Lindlar's catalyst 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 5.5h， 生成 4-((2R,3R)-3-((E)-((2R,3R)-3-((4-methoxybenzyl)oxy)-2-((Z)-oct-2-en-1-yl)-5-oxocyclopentylidene)methyl)oxiran-2-yl)butanoic acid
  参考文献：
  名称：

  Synthesis of the PMB Ether of 5,6-Epoxyisoprostane E2 through Aldol Reaction of the α-Bromocyclopentanone

  摘要：

  5,6-Epoxyisoprostane E2 was synthesized via bromohydrination of the cyclopentene and aldol reaction of the alpha-bromocyclopentanone with the epoxyaldehyde. High regioselectivity in the bromohydrination was attained with recrystallized NBS and pyridine in aqueous DMSO. The enolate for the aldol reaction was generated by adding t-BuLi to the mixture of the a-bromocyclopentanone and ZnI2. This aldol protocol was applied successfully to several cyclopentanones and aldehydes.

  DOI：

  10.1021/ol500654g
• 作为产物：
  描述：

  (3R,4R)-2-[[(2R,3R)-3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]oxiran-2-yl]-hydroxymethyl]-4-[(4-methoxyphenyl)methoxy]-3-oct-2-ynylcyclopentan-1-one 在 4-二甲氨基吡啶 、 aluminum oxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (3R,4R,E)-2-(((2R,3R)-3-(4-((tert-butyldimethylsilyl)oxy)butyl)oxiran-2-yl)methylene)-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone
  参考文献：
  名称：

  Synthesis of the PMB Ether of 5,6-Epoxyisoprostane E2 through Aldol Reaction of the α-Bromocyclopentanone

  摘要：

  5,6-Epoxyisoprostane E2 was synthesized via bromohydrination of the cyclopentene and aldol reaction of the alpha-bromocyclopentanone with the epoxyaldehyde. High regioselectivity in the bromohydrination was attained with recrystallized NBS and pyridine in aqueous DMSO. The enolate for the aldol reaction was generated by adding t-BuLi to the mixture of the a-bromocyclopentanone and ZnI2. This aldol protocol was applied successfully to several cyclopentanones and aldehydes.

  DOI：

  10.1021/ol500654g