ethyl 2-acetyloxy-4-(3-chlorophenyl)-3-nitrobut-3-enoate | 1394173-92-2

• 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: ethyl 2-acetyloxy-4-(3-chlorophenyl)-3-nitrobut-3-enoate
• CAS: 1394173-92-2
• 化学式: C₁₄H₁₄ClNO₆
• 分子量: 327.721
• InChiKey: UHBHPQNHEFTSMO-UHFFFAOYSA-N

物化性质

• 沸点：
  473.5±45.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-巯基吡啶 、 ethyl 2-acetyloxy-4-(3-chlorophenyl)-3-nitrobut-3-enoate 在 2,6-二甲基吡啶 作用下， 以 二硫化碳 为溶剂， 以50%的产率得到ethyl 3-(3-chlorophenyl)indolizine-1-carboxylate
  参考文献：
  名称：

  通过2-巯基吡啶与硝基烯丙基乙酸酯之间的Domino SN2 / Michael加成反应合成吲哚类化合物的不寻常途径

  摘要：

  已证明2-巯基吡啶与乙酸烯丙酯之间存在异常反应。该反应由在三级中心包括S N 2反应的多米诺序列引发，然后进行迈克尔加成并去除硫部分以递送取代的吲哚嗪。

  DOI：

  10.1002/ejoc.201801426

文献信息

• Kinetic Resolution of Activated Nitroallylic Acetates with Aldehydes and Ketones through a Conjugate Addition-Elimination SN2′ Process
  作者：Raju Jannapu Reddy、Pei-Hsun Lee、Dhananjay R. Magar、Jung-Hsuan Chen、Kwunmin Chen

  DOI：10.1002/ejoc.201101162

  日期：2012.1

  A unique organocatalytic kinetic resolution (KR) of nitroallylic acetates has been developed. A variety of racemic nitroallylic acetates (1a–n) were resolved with chiral enamines formed in situ from the reaction of aldehydes and ketones with organocatalyst 2b (2.5 mol-%) and 14c (20 mol-%), respectively, through an interesting SN2′ reaction. The densely functionalized products 3–5 were obtained with

  已开发出硝基烯丙基乙酸酯的独特有机催化动力学拆分 (KR)。各种外消旋硝基烯丙基乙酸酯 (1a-n) 分别由醛和酮与有机催化剂 2b (2.5 mol-%) 和 14c (20 mol-%) 反应形成的手性烯胺通过有趣的 SN2 分离' 反应。以高到高的立体选择性（高达> 99:1 dr 和> 99 % ee）以良好到高的化学产率获得了密集功能化的产品 3-5。未反应的起始底物 1a-n 以良好到高的光学纯度（高达 98% ee）回收。动力学拆分的范围和通用性被扩展到包括各种醛和酮作为供体来源的各种硝基烯丙基乙酸酯。确定官能化产物和未反应底物的绝对立体化学。当 (S)-香茅醛在 2b 存在下用 rac-1a 处理得到 12 作为单一非对映异构体，进一步环化得到具有优异立体选择性的四取代环己烷衍生物 13 时，证明了合成应用。提出了过渡态模型来解释 KR 过程中的立体化学偏差。
• Silica gel-Mediated Friedel-Crafts Reaction of Indoles with Functionalized Nitroallylic Acetates via an SN1 Process
  作者：Ching-Yin Ho、Suparna Roy、Yan-Ming Chen、Kwunmin Chen

  DOI：10.1002/jccs.201100643

  日期：2012.8

  An environmentally friendly Friedel‐Crafts reaction was demonstrated between indoles and functionalized nitroallylic acetates in the presence of silica gel, providing the corresponding C‐3‐selective regioisomers in good to high overall chemical yields (70‐93%).

  在硅胶存在下，吲哚和官能化的硝基烯丙基乙酸酯之间发生了环保的Friedel-Crafts反应，证明了相应的C-3选择区域异构体具有良好的化学总收率（70-93％）。
• The combination of domino process and kinetic resolution: organocatalytic synthesis of functionalised cyclopentenes by sequential SN2′-Michael reaction
  作者：Lun Fu Yeh、Shaik Anwar、Kwunmin Chen

  DOI：10.1016/j.tet.2012.06.085

  日期：2012.9

  An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S(N)2'-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee). (C) 2012 Published by Elsevier Ltd.
• An Unusual Route to Synthesize Indolizines through a Domino S _N 2/Michael Addition Reaction Between 2‐Mercaptopyridine and Nitroallylic Acetates
  作者：Suparna Roy

  DOI：10.1002/ejoc.201801426

  日期：2019.1.31

  An unusual reaction between 2‐mercaptopyridine and nitroallylic acetates has been demonstrated. The reaction is initiated by a domino sequence including an SN2 reaction at tertiary center followed by a Michael addition and removal of sulfur moiety to deliver substituted indolizines.

  已证明2-巯基吡啶与乙酸烯丙酯之间存在异常反应。该反应由在三级中心包括S N 2反应的多米诺序列引发，然后进行迈克尔加成并去除硫部分以递送取代的吲哚嗪。