cyano-(3,4-dichlorophenyl)acetic acid methyl ester | 849589-04-4

• 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: cyano-(3,4-dichlorophenyl)acetic acid methyl ester
• 英文别名: methyl cyano(3,4-dichlorophenyl)acetate；methyl [2-cyano-2-(3,4-dichlorophenyl)]acetate；Methyl 2-cyano-2-(3,4-dichlorophenyl)acetate
• CAS: 849589-04-4
• 化学式: C₁₀H₇Cl₂NO₂
• 分子量: 244.077
• InChiKey: XURZHUOKWKYITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyano-(3,4-dichlorophenyl)acetic acid methyl ester 在 bis(η3-allyl-μ-chloropalladium(II)) 、 chiral pocket ligands 作用下， 反应 0.5h， 生成 2-cyano-2-(3,4-dichlorophenyl)-pent-4-enoic acid isopropyl ester
  参考文献：
  名称：

  Catalytic enantioselective allylation at the activated benzylic position of prochiral aryl cyano esters: access to quaternary stereogenic centers

  摘要：

  Palladium catalyzed asymmetric allylic alkylation of prochiral aryl cyano esters has been carried out in the presence of various chiral ligands. The base and additives have been varied and allowed to produce the allyl derivative presenting a highly functionalized quaternary stereogenic center. The chiral pocket ligands of Trost appears the most appropriate to produce the desired chiral derivative. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.082
• 作为产物：
  描述：

  碳酸二甲酯 、 3,4-二氯苯乙腈 在 sodium methylate 作用下， 以 甲苯 为溶剂， 以100%的产率得到cyano-(3,4-dichlorophenyl)acetic acid methyl ester
  参考文献：
  名称：

  Catalytic enantioselective allylation at the activated benzylic position of prochiral aryl cyano esters: access to quaternary stereogenic centers

  摘要：

  Palladium catalyzed asymmetric allylic alkylation of prochiral aryl cyano esters has been carried out in the presence of various chiral ligands. The base and additives have been varied and allowed to produce the allyl derivative presenting a highly functionalized quaternary stereogenic center. The chiral pocket ligands of Trost appears the most appropriate to produce the desired chiral derivative. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.082

文献信息

• Acetone Cyanohydrin as a Source of HCN in the Cu-Catalyzed Hydrocyanation of α-Aryl Diazoacetates
  作者：Eun Ju Park、Seungeon Lee、Sukbok Chang

  DOI：10.1021/jo100356d

  日期：2010.4.16

  A procedure for the Cu-catalyzed hydrocyanation of α-aryl diazoesters has been developed using acetone cyanohydrin as a source of hydrogen cyanide (HCN). It was found that the addition of trimethylsilyl cyanide (TMSCN) significantly accelerates the conversion presumably by delivering free cyanide ion in situ, thus producing various types of α-aryl cyanoacetates in high yields under mild conditions

  已经开发了使用丙酮氰醇作为氰化氢（HCN）源的Cu催化α-芳基重氮酸酯氢氰化的方法。已经发现，添加三甲基甲硅烷基氰化物（TMSCN）可以通过原位释放游离氰离子来显着加速转化，从而在温和条件下以高收率生产各种类型的α-芳基氰乙酸酯。
• Highly Selective Preparation of a Chiral Quaternary Allyl Aryl Piperidinedione by Palladium-Catalyzed Asymmetric Allylation Under Solid-Liquid Phase-Transfer Catalysis
  作者：Audrey Nowicki、Jérôme Keldenich、Francine Agbossou-Niedercorn

  DOI：10.1002/ejoc.200700670

  日期：2007.12

  The combination of a chiral palladium catalyst and a solid–liquid phase-transfer catalyst provides an effective method for the chemo- and enantioselective preparation of the chiral quaternary center of an allyl aryl piperidinedione. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  手性钯催化剂和固液相转移催化剂的结合为烯丙基芳基哌啶二酮手性季中心的化学和对映选择性制备提供了一种有效的方法。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Construction of quaternary carbon stereocentres: catalytic enantioselective allylation assisted by a bimetallic catalytic system
  作者：Audrey Nowicki、André Mortreux、Francine Agbossou-Niedercorn

  DOI：10.1016/j.tetasy.2005.02.009

  日期：2005.4

  The asymmetric allylic alkylation of prochiral aryl cyano esters has been carried out in the presence of a bi-component catalytic system containing a palladium and a rhodium complex modified by phosphorus containing chiral auxiliaries. The allyl derivatives were isolated in up to 63% ee. The chiral pocket ligands of Trost appear the most appropriate to produce the desired chiral derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
• Catalytic enantioselective allylation at the activated benzylic position of prochiral aryl cyano esters: access to quaternary stereogenic centers
  作者：Audrey Nowicki、André Mortreux、Francine Agbossou-Niedercorn

  DOI：10.1016/j.tetlet.2005.01.082

  日期：2005.3

  Palladium catalyzed asymmetric allylic alkylation of prochiral aryl cyano esters has been carried out in the presence of various chiral ligands. The base and additives have been varied and allowed to produce the allyl derivative presenting a highly functionalized quaternary stereogenic center. The chiral pocket ligands of Trost appears the most appropriate to produce the desired chiral derivative. (C) 2005 Elsevier Ltd. All rights reserved.