(2SR,3SR)-methyl 3-(4-methoxyphenyl)-2-phenyloxirane-2-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2SR,3SR)-methyl 3-(4-methoxyphenyl)-2-phenyloxirane-2-carboxylate
• 英文别名: methyl 3-(4-methoxyphenyl)-2-phenyloxirane-2-carboxylate；methyl (2R,3R)-3-(4-methoxyphenyl)-2-phenyloxirane-2-carboxylate
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: LCAGWZKWOSFLBF-NVXWUHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  a-叠氮基-苯乙酸甲酯 、 4-甲氧基苯甲醛 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(2SR,3SR)-methyl 3-(4-methoxyphenyl)-2-phenyloxirane-2-carboxylate
  参考文献：
  名称：

  来自重氮乙酸酯的环氧化物和氮丙啶通过叶立德中间体。

  摘要：

  报道了一种有效的方法，该方法通过乙酸羰基铑（II）催化苯基-和苯乙烯基重氮乙酸酯与醛，酮或亚胺的反应，经由羰基叶立德中间体进行立体定向环氧化和叠氮化。

  DOI：

  10.1021/ol015600x

文献信息

• Epoxides and Aziridines from Diazoacetates via Ylide Intermediates
  作者：Michael P. Doyle、Wenhao Hu、Daren J. Timmons

  DOI：10.1021/ol015600x

  日期：2001.3.1

  An effective methodology is reported for stereospecific epoxidation and aziridination via carbonyl ylide intermediates using rhodium(II) acetate catalyzed reactions of phenyl- and styryldiazoacetates with aldehydes, ketones, or imines.

  报道了一种有效的方法，该方法通过乙酸羰基铑（II）催化苯基-和苯乙烯基重氮乙酸酯与醛，酮或亚胺的反应，经由羰基叶立德中间体进行立体定向环氧化和叠氮化。
• Highly Chemoselective 2,4,5-Triaryl-1,3-dioxolane Formation from Intermolecular 1,3-Dipolar Addition of Carbonyl Ylide with Aryl Aldehydes
  作者：Chong-Dao Lu、Zhi-Yong Chen、Hui Liu、Wen-Hao Hu、Ai-Qiao Mi

  DOI：10.1021/ol0489494

  日期：2004.9.1

  [reaction: see text] Rhodium(II) acetate catalyzed 1,3-dipolar cycloaddition of methyl phenyldiazoacetate with a mixture of electron-rich and electron-deficient aryl aldehydes gave 1,3-dioxolanes in high yield with excellent chemoselectivity.

  [反应：参见正文]乙酸铑（II）催化苯基重氮乙酸甲酯与富电子和缺电子的芳基醛混合物的1,3-偶极环加成反应，以高收率提供了1,3-二氧戊环，具有出色的化学选择性。
• The rhodium catalyzed three-component reaction of diazoacetates, titanium(iv) alkoxides and aldehydes
  作者：Chong-Dao Lu、Hui Liu、Zhi-Yong Chen、Wen-Hao Hu、Ai-Qiao Mi

  DOI：10.1039/b502093j

  日期：——

  The rhodium(II)-catalyzed three-component reaction of diazoacetates, titanium alkoxides and aldehydes is shown to give alpha-alkoxyl-beta-hydroxyl acid derivatives; the novel C-C bond formation reaction is proposed to occur through oxonium ylides derived from diazo compounds and titanium alkoxides, and followed by intermolecular trapping by aldehydes.

  铑（II）催化的重氮乙酸盐，钛醇盐和醛的三组分反应可生成α-烷氧基-β-羟基酸衍生物。提出了一种新的CC键形成反应，该反应通过重氮化合物和钛的醇盐衍生的氧代鎓盐发生，然后通过醛进行分子间捕集。
• Oxirane synthesis from diazocarbonyl compounds via NHC-Ag+ catalysis
  作者：Zhen Wang、Jian Wen、Qing-Wei Bi、Xiao-Qi Xu、Zhu-Qing Shen、Xiao-Xiao Li、Zili Chen

  DOI：10.1016/j.tetlet.2014.03.105

  日期：2014.4

  A new method was developed to synthesize oxirane products from the reaction of diazocarbonyl substrates with aryl aldehydes by using Ag(l) N-heterocyclic carbene complex as the catalyst. A combination of N-heterocyclic carbene silver complex (IPrAgCI) with another silver salt (AgOTf) generated the catalytic active IPr-Ag+ intermediate, which then catalyzed the epoxidation reaction. (C) 2014 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of epoxides by reaction of donor/acceptor-substituted carbenoids with α,β-unsaturated aldehydes
  作者：Huw M.L Davies、Jason DeMeese

  DOI：10.1016/s0040-4039(01)01415-0

  日期：2001.9

  The reaction of donor/acceptor-substituted carbenoids with alpha,beta -unsaturated aldehydes results in the highly diastereoselective synthesis of epoxides. (C) 2001 Published by Elsevier Science Ltd.