(Z)-methyl 2-(chloromethyl)-3-(4-nitrophenyl)acrylate | 682350-75-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 2-(chloromethyl)-3-(4-nitrophenyl)acrylate
• 英文别名: methyl (Z)-2-chloromethyl-3-(4-nitrophenyl)propenoate；methyl (Z)-2-(chloromethyl)-3-(4-nitrophenyl)prop-2-enoate
• CAS: 682350-75-0
• 化学式: C₁₁H₁₀ClNO₄
• 分子量: 255.658
• InChiKey: MSSSWLODWVEOOX-RMKNXTFCSA-N

物化性质

• 熔点：
  126-128 °C
• 沸点：
  364.8±37.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-(chloromethyl)-3-(4-nitrophenyl)acrylate 在 四丁基溴化铵 CHIRALCEL OD 作用下， 以 四氢呋喃 、 正己烷 、 异丙醇 为溶剂， 反应 0.42h， 生成 (R)-methyl 2-methylene-3-(4-nitrophenyl)pentanoate
  参考文献：
  名称：

  Expedient synthesis of β,β-disubstituted α-methylenepropionates

  摘要：

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.002
• 作为产物：
  描述：

  2-[羟基-(4-硝基-苯基)-甲基]-丙烯酸甲酯 在 四氯化碳 、 三苯基膦 作用下， 反应 3.0h， 以96%的产率得到(Z)-methyl 2-(chloromethyl)-3-(4-nitrophenyl)acrylate
  参考文献：
  名称：

  使用 PPh3/CCl4 氯化 Baylis-Hillman 加合物的简单有效方案

  摘要：

  PPh 3 /CCl 4 系统已被用于从 Baylis-Hillman 加合物以优异的收率立体选择性合成 (Z)- 和 (£)-烯丙基氯。

  DOI：

  10.1246/cl.2008.512

文献信息

• A Simple and Efficient Protocol for Chlorination of Baylis–Hillman Adducts Using PPh₃/CCl₄
  作者：Biswanath Das、Boddu Shashi Kanth、Kongara Ravinder Reddy、Gandham Satyalakshmi、Rathod Aravind Kumar

  DOI：10.1246/cl.2008.512

  日期：2008.5.5

  PPh 3 /CCl 4 system has been employed for the stereoselective synthesis of (Z)- and ( £ )-allyl chlorides from Baylis-Hillman adducts in excellent yields.

  PPh 3 /CCl 4 系统已被用于从 Baylis-Hillman 加合物以优异的收率立体选择性合成 (Z)- 和 (£)-烯丙基氯。
• A Mild and Efficient Method for Chlorination ofBaylis–Hillman Adducts Using PPh3/Cl3CCONH2
  作者：Biswanath Das、Nikhil Chowdhury、Kongara Damodar、Bommena Ravikanth

  DOI：10.1002/hlca.200790211

  日期：2007.10

  A new and convenient stereoselective synthesis of (Z)-2-(chloromethyl)alk-2-enoates has been achieved from Baylis–Hillman adducts by treatment with PPh3/Cl3CCONH2 at room temperature. The synthesis can proceed under mild and acid-free conditions to form the products in high yields.

  通过在室温下用PPh 3 / Cl 3 CCONH 2处理，从Baylis-Hillman加合物获得了一种新的且方便的立体选择合成（Z）-2-（氯甲基）alk-2-enoates的方法。合成可以在温和且无酸的条件下进行，从而以高收率形成产物。
• Enantioselective Preparation of ?,?-Disubstituted ?-Methylenepropionates by MAO Promotion of the Zinc Schlenk Equilibrium
  作者：Paul J. Goldsmith、Simon J. Teat、Simon Woodward

  DOI：10.1002/anie.200463028

  日期：2005.4.8
• Convenient and efficient stereoselective synthesis of (2Z)-2-(chloromethyl)alk-2-enoates using iron(III) or indium(III) chloride
  作者：Biswanath Das、Joydeep Banerjee、Nasi Ravindranath、Bollu Venkataiah

  DOI：10.1016/j.tetlet.2004.01.101

  日期：2004.3

  The stereoselective synthesis of (2Z)-2-(chloromethyl)alk-2-enoates has been achieved efficiently and in high yields and in short reaction times from Baylis-Hillman adducts, 3-hydroxy-2-methylene-alkanoates, by treatment with FeCl3 or InCl3 at room temperature. (C) 2004 Elsevier Ltd. All rights reserved.
• Expedient synthesis of β,β-disubstituted α-methylenepropionates
  作者：Kallolmay Biswas、Christoph Börner、Josepe Gimeno、Paul J. Goldsmith、Daniella Ramazzotti、Angela L.K. So、Simon Woodward

  DOI：10.1016/j.tet.2004.12.002

  日期：2005.2

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.