(E)-1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene | 389838-11-3

• 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: (E)-1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene
• 英文别名: 1-[(E)-2-(4-methylphenyl)-1-nitroethenyl]-2-methylsulfanylbenzene
• CAS: 389838-11-3
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: XHXVBVQUDOEYOX-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene 在 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-nitro-3-(p-tolyl)thiochroman S,S-dioxide
  参考文献：
  名称：

  到4- nitrothiochroman容易访问小号，小号经由环放大-dioxides从3-硝基苯并[ b ]噻吩

  摘要：

  （E）-2-芳基-1- [2-（甲硫基）苯基] -1-硝基乙烯5可以很容易地氧化成相关的砜6并在用双（三甲基甲硅烷基）锂金属化后通过分子内迈克尔加成反应有效地进行环化酰胺在THF中的溶液。用氯化铵淬灭后，以非对映异构体混合物的形式获得3-芳基-4-硝基硫代苯并二氢吡喃S 2，S-二氧化物2，收率良好至优异。闭环步骤的产率和立体化学似乎都受到3-芳基部分的空间效应的影响。由于硫化物5源自3-硝基苯并[ b ]噻吩（1），整个1到2的过程可以被认为是硫杂环的5到6个环的有效扩环。还完成了对分离的非对映异构体2的构象1 H NMR和分子力学研究。

  DOI：

  10.1016/j.tet.2004.04.039
• 作为产物：
  描述：

  3-硝基苯并噻吩 在 silver nitrate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (E)-1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene
  参考文献：
  名称：

  Ring opening of 2-substituted 4-nitrothiophenes with pyrrolidine. Access to new functionalized nitro-unsaturated building blocks

  摘要：

  The reaction conditions of the ring-opening processes of 3-nitrothiophene 7a and of 3-nitrobenzo[b]thiophene 7b with pyrrolidine and silver nitrate were optimized as well as those of the subsequent S-methylation of the ensuing silver enethiolates 8a and 8b to 4-methylthio-2-nitro-1-pyrrolidino-1,3-butadiene 9a and 1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene 9b. Under such conditions 2-X-substituted 4-nitrothiophenes 7c-i consistently gave good yields of the corresponding 4-methylthio-2-nitro-1-pyrrolidino-4-X-1,3-butadienes 9c-i. The nitroenamine derivatives 9a-i were then reacted with p-tolylmagnesium bromide to furnish moderate to good yields of 4-methylthio-2-nitro-1-(p-tolyl)-4-X-1,3-butadienes 10a,c-i and 1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene 10b. Stereochemistry of the interesting building blocks 9a-i and 10a-i was assigned on the grounds of H-1 NMR data and NOE experiments. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00765-7

文献信息

• Easy access to 4-nitrothiochroman S,S-dioxides via ring-enlargement from 3-nitrobenzo[b]thiophene
  作者：Lara Bianchi、Carlo Dell'Erba、Massimo Maccagno、Stefano Morganti、Marino Novi、Giovanni Petrillo、Egon Rizzato、Fernando Sancassan、Elda Severi、Domenico Spinelli、Cinzia Tavani

  DOI：10.1016/j.tet.2004.04.039

  日期：2004.5

  easily be oxidized to the relevant sulfones 6 and effectively subjected to cyclization via an intramolecular Michael addition after metallation with lithium bis(trimethylsilyl)amide in THF. After quenching with ammonium chloride the 3-aryl-4-nitrothiochroman S,S-dioxides 2 are obtained as diastereomeric mixtures in good to excellent yields. Both yields and stereochemistry of the ring-closure step appear

  （E）-2-芳基-1- [2-（甲硫基）苯基] -1-硝基乙烯5可以很容易地氧化成相关的砜6并在用双（三甲基甲硅烷基）锂金属化后通过分子内迈克尔加成反应有效地进行环化酰胺在THF中的溶液。用氯化铵淬灭后，以非对映异构体混合物的形式获得3-芳基-4-硝基硫代苯并二氢吡喃S 2，S-二氧化物2，收率良好至优异。闭环步骤的产率和立体化学似乎都受到3-芳基部分的空间效应的影响。由于硫化物5源自3-硝基苯并[ b ]噻吩（1），整个1到2的过程可以被认为是硫杂环的5到6个环的有效扩环。还完成了对分离的非对映异构体2的构象1 H NMR和分子力学研究。
• Ring opening of 2-substituted 4-nitrothiophenes with pyrrolidine. Access to new functionalized nitro-unsaturated building blocks
  作者：Carlo Dell'Erba、Antonella Gabellini、Marino Novi、Giovanni Petrillo、Cinzia Tavani、Barbara Cosimelli、Domenico Spinelli

  DOI：10.1016/s0040-4020(01)00765-7

  日期：2001.9

  The reaction conditions of the ring-opening processes of 3-nitrothiophene 7a and of 3-nitrobenzo[b]thiophene 7b with pyrrolidine and silver nitrate were optimized as well as those of the subsequent S-methylation of the ensuing silver enethiolates 8a and 8b to 4-methylthio-2-nitro-1-pyrrolidino-1,3-butadiene 9a and 1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene 9b. Under such conditions 2-X-substituted 4-nitrothiophenes 7c-i consistently gave good yields of the corresponding 4-methylthio-2-nitro-1-pyrrolidino-4-X-1,3-butadienes 9c-i. The nitroenamine derivatives 9a-i were then reacted with p-tolylmagnesium bromide to furnish moderate to good yields of 4-methylthio-2-nitro-1-(p-tolyl)-4-X-1,3-butadienes 10a,c-i and 1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene 10b. Stereochemistry of the interesting building blocks 9a-i and 10a-i was assigned on the grounds of H-1 NMR data and NOE experiments. (C) 2001 Elsevier Science Ltd. All rights reserved.