(S)-3,4,5-trimethoxyphenyloxirane | 177472-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3,4,5-trimethoxyphenyloxirane
• 英文别名: (2S)-2-(3,4,5-trimethoxyphenyl)oxirane
• CAS: 177472-80-9
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: WXBAEPCTXMEJNV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3,4,5-trimethoxyphenyloxirane 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 考布他汀
  参考文献：
  名称：

  Enantioselective synthesis of natural combretastatin

  摘要：

  In a process which appears to be general for the enantioselective synthesis of oxysubstituted 1,2-diarylethanols, a 4-methoxy-3-silyloxyphenyllithium, obtained by bromine-lithium exchange from the corresponding aryl bromide and t-butyllithium, added selectively at the b-carbon of (S)-2,3,4-trimethoxyphenyloxirane, elaborated from the corresponding styrene via Sharpless asymmetric dihydroxylation, to afford an adduct from which natural (-)-combretastatin was obtained by desilylation. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00115-2
• 作为产物：
  描述：

  (S)-1-(3,4,5-trimethoxyphenyl)-1,2-ethanediol 在 吡啶 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-3,4,5-trimethoxyphenyloxirane
  参考文献：
  名称：

  Enantioselective synthesis of natural combretastatin

  摘要：

  In a process which appears to be general for the enantioselective synthesis of oxysubstituted 1,2-diarylethanols, a 4-methoxy-3-silyloxyphenyllithium, obtained by bromine-lithium exchange from the corresponding aryl bromide and t-butyllithium, added selectively at the b-carbon of (S)-2,3,4-trimethoxyphenyloxirane, elaborated from the corresponding styrene via Sharpless asymmetric dihydroxylation, to afford an adduct from which natural (-)-combretastatin was obtained by desilylation. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00115-2

文献信息

• S-Methylidene agents: preparation of chiral non-racemic heterocycles
  作者：David C. Forbes、Sampada V. Bettigeri、Samit A. Patrawala、Susanna C. Pischek、Michael C. Standen

  DOI：10.1016/j.tet.2008.10.019

  日期：2009.1

  Reaction of sulfur ylide with aldehyde, imine, and ketone functionality affords the desired three-membered heterocycle in excellent yield. The sulfur ylide is generated in situ upon decarboxylation of carboxymethylsulfonium betaine functionality. Of the seven carboxymethylsulfonium betaine derivatives surveyed, the highest level of conversion of π-acceptor to heterocycle was obtained with the one having

  硫叶立德与醛、亚胺和酮官能团的反应以优异的产率提供所需的三元杂环。在羧甲基锍甜菜碱官能团脱羧后原位生成硫叶立德。在调查的七种羧甲基锍甜菜碱衍生物中，π-受体转化为杂环的水平最高，其中含有S-甲基和S-苯基官能团与硫代乙酸酯衍生物结合。涉及羧甲基锍甜菜碱官能团脱羧的亚甲基氮丙啶化和环氧化以反应方案、转化水平和范围的优势补充了现有技术。虽然在亚胺官能团的氮丙啶化中观察到中等水平的非对映控制，但使用 Jacobsen 的 Co(II)-salen 络合物解析的四种环氧乙烷均以高产率和对映选择性获得。分离出的手性非外消旋环氧乙烷分别以 3-溴-4-甲氧基苯甲醛和 3,4,5-三甲氧基苯甲醛为原料，正式合成 chelonin B 和考布他汀。
• Enantioselective synthesis of natural combretastatin
  作者：Alessio Ramacciotti、Rita Fiaschi、Elio Napolitano

  DOI：10.1016/0957-4166(96)00115-2

  日期：1996.4

  In a process which appears to be general for the enantioselective synthesis of oxysubstituted 1,2-diarylethanols, a 4-methoxy-3-silyloxyphenyllithium, obtained by bromine-lithium exchange from the corresponding aryl bromide and t-butyllithium, added selectively at the b-carbon of (S)-2,3,4-trimethoxyphenyloxirane, elaborated from the corresponding styrene via Sharpless asymmetric dihydroxylation, to afford an adduct from which natural (-)-combretastatin was obtained by desilylation. Copyright (C) 1996 Elsevier Science Ltd