(Z)-3-甲氧基丙烯腈 | 69194-04-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (Z)-3-甲氧基丙烯腈
• 英文名称: (Z)-3-methoxypropenenitrile
• 英文别名: (Z)-methylcyanovinyl ether；cis-3-methoxy-acrylonitrile；cis-β-Methoxy-acrylnitril；(z)-3-Methoxy-2-propenenitrile；(Z)-3-methoxyprop-2-enenitrile
• CAS: 69194-04-3
• 化学式: C₄H₅NO
• 分子量: 83.0898
• InChiKey: IPCRTSDORDQHRO-RQOWECAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙醇 、 (Z)-3-甲氧基丙烯腈 、 3-甲氧基-2-烯腈 在 双(乙腈)氯化钯(II) 作用下， 反应 36.02h， 生成 3-乙氧基丙烯酸乙酯 、 (Z)-3-ethoxyacrylonitrile
  参考文献：
  名称：

  置換ビニルエーテル誘導体の製造方法

  摘要：

  待解决问题：提供一种通过醚交换从具有电子吸引基团作为双键碳原子上取代基的取代乙烯醚中产生取代乙烯醚衍生物的方法，以使结合位点成为电子不足的情况。 解决方案：制备取代乙烯醚衍生物的方法包括将至少具有一个电子吸引基团作为形成碳-碳双键的碳原子的取代乙烯醚与醇或酚在含有周期表中9和/或10金属群化合物的催化剂存在下进行醚交换反应，其中该化合物具有反离子，当该离子质子化时，质子具有离解常数（pKa）为0或更低。 版权所有：（C）2005，JPO＆NCIPI

  公开号：

  JP2005170912A
• 作为产物：
  描述：

  3-甲氧基丙烯腈 在 recombinant nitrilase AtNIT₁ from Arabidopsis thailana 、 Tris*HCl buffer 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以30%的产率得到(E)-3-甲氧基丙烯酸
  参考文献：
  名称：

  (E)-Selective hydrolysis of (E,Z)-α,β-unsaturated nitriles by the recombinant nitrilase AtNIT1 from Arabidopsis thaliana

  摘要：

  From stereoisomeric alpha,beta -unsaturated nitriles (E,Z)-1, the recombinant nitrilase AtNlTl from Arabidopsis thaliana hydrolyses the (E)-isomers exclusively to the corresponding (E)-carboxylic acids (E)-2 with high specificity. The (E)-selectivity can also be utilised for the preparation of the isomerically pure nitriles (Z)-1, From (E,Z)-2-hydroxycinnamonitrile (E,Z)-3, the otherwise difficult obtainable (Z)-3 was prepared in 66% isolated yield. With beta,gamma -unsaturated (E,Z)-3-heptenenitrile (E,Z)-4. however, (E)-selectivity was not observed. AtNlTl exhibits not only diastereoselectivity but also regioselectivity. From a mixture of the four isomers A-D of 3-(2-cyanocyclohex-3-enyl)propenenitrile 6, exclusively isomer D ((E)-cis-6) was hydrolysed to 3-(2-cyanocyclohex-3-enyl)propenoic acid (E)-cis-7. as stated by X-ray crystal structure. Only after complete conversion of D and high enzyme concentrations, isomer C ((E)-trans-6) was hydrolysed to a small extent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00449-9

文献信息

• The Synthesis and Reactions of β-Chloroacrylonitrile
  作者：F. Scotti、E. J. Frazza

  DOI：10.1021/jo01030a033

  日期：1964.7
• Prochazka, Milos; Zaruba, Arno, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 1, p. 89 - 95
  作者：Prochazka, Milos、Zaruba, Arno

  DOI：——

  日期：——
• (E)-Selective hydrolysis of (E,Z)-α,β-unsaturated nitriles by the recombinant nitrilase AtNIT1 from Arabidopsis thaliana
  作者：Franz Effenberger、Steffen Oßwald

  DOI：10.1016/s0957-4166(01)00449-9

  日期：2001.10

  From stereoisomeric alpha,beta -unsaturated nitriles (E,Z)-1, the recombinant nitrilase AtNlTl from Arabidopsis thaliana hydrolyses the (E)-isomers exclusively to the corresponding (E)-carboxylic acids (E)-2 with high specificity. The (E)-selectivity can also be utilised for the preparation of the isomerically pure nitriles (Z)-1, From (E,Z)-2-hydroxycinnamonitrile (E,Z)-3, the otherwise difficult obtainable (Z)-3 was prepared in 66% isolated yield. With beta,gamma -unsaturated (E,Z)-3-heptenenitrile (E,Z)-4. however, (E)-selectivity was not observed. AtNlTl exhibits not only diastereoselectivity but also regioselectivity. From a mixture of the four isomers A-D of 3-(2-cyanocyclohex-3-enyl)propenenitrile 6, exclusively isomer D ((E)-cis-6) was hydrolysed to 3-(2-cyanocyclohex-3-enyl)propenoic acid (E)-cis-7. as stated by X-ray crystal structure. Only after complete conversion of D and high enzyme concentrations, isomer C ((E)-trans-6) was hydrolysed to a small extent. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 置換ビニルエーテル誘導体の製造方法
  申请人：三菱化学株式会社

  公开号：JP2005170912A

  公开（公告）日：2005-06-30

  PROBLEM TO BE SOLVED: To provide a method for producing a substituted vinyl ether derivative by ether exchange from a substituted vinyl ether which has an electron-attracting group as a substituent on a double bond carbon atom to cause the binding site to be electron-deficient.

  SOLUTION: The method for producing a substituted vinyl ether derivative comprises subjecting a substituted vinyl ether, which has at least one electron-attracting group as a substituent on a carbon atom which forms carbon-carbon double bond, to ether exchange reaction with an alcohol or a phenol in the presence of a catalyst containing a compound of the group 9 and/or 10 metal in the periodic table, wherein the compound has a counter anion, and when the anion is protonated, the proton has an ionization constant (pKa) of 0 or less.

  COPYRIGHT: (C)2005,JPO&NCIPI

  待解决问题：提供一种通过醚交换从具有电子吸引基团作为双键碳原子上取代基的取代乙烯醚中产生取代乙烯醚衍生物的方法，以使结合位点成为电子不足的情况。 解决方案：制备取代乙烯醚衍生物的方法包括将至少具有一个电子吸引基团作为形成碳-碳双键的碳原子的取代乙烯醚与醇或酚在含有周期表中9和/或10金属群化合物的催化剂存在下进行醚交换反应，其中该化合物具有反离子，当该离子质子化时，质子具有离解常数（pKa）为0或更低。 版权所有：（C）2005，JPO＆NCIPI

表征谱图