(E)-4-(4-methylphenyl)-1,1-bis(methylthio)-3-nitro-1,3-butadiene | 389838-14-6

• 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: (E)-4-(4-methylphenyl)-1,1-bis(methylthio)-3-nitro-1,3-butadiene
• 英文别名: (1E)-4,4-bis(methylthio)-2-nitro-1-(p-tolyl)-1,3-butadiene；1-[(1E)-4,4-bis(methylsulfanyl)-2-nitrobuta-1,3-dienyl]-4-methylbenzene
• CAS: 389838-14-6
• 化学式: C₁₃H₁₅NO₂S₂
• 分子量: 281.4
• InChiKey: KRUNMFHFWDDROD-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-methylphenyl)-1,1-bis(methylthio)-3-nitro-1,3-butadiene 在 lead 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到3-hydroxyimino-4-(4-methylphenyl)-1,1-bis(methylthio)-1-butene
  参考文献：
  名称：

  Access to 3-arylmethyl-5-(methylthio)isoxazoles via an initial ring-opening of 2-methylthio-4-nitrothiophene

  摘要：

  The reactions of 1, 1 -bis(methylthio)-3-nitro-4-pyrrolidino-1.3-butadiene (deriving from the initial ring-opening of 2-methylthio-4-nitrothiophene with pyrrolidine and silver nitrate in EtOH) with arylmagnesium bromides result in the chemoselective replacement of the pyrrolidino group with the aryl moiety of the Grignards. The 4-aryl-1,1-bis(methylthio)-3-nitro-1,3-butadienes thus obtained are the key intermediates for the effective synthesis, through the corresponding reduction products 4-aryl-3-hydroximino-1, 1-bis(methylthio)-1-butenes, of the previously unknown 3-arylmethyl-5-(methylthio)isoxazoles. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00292-2
• 作为产物：
  描述：

  对甲苯基溴化镁 、 (1E)-4,4-bis(methylthio)-2-nitro-1-pyrrolidino-1,3-butadiene 以 四氢呋喃 为溶剂， 以86%的产率得到(E)-4-(4-methylphenyl)-1,1-bis(methylthio)-3-nitro-1,3-butadiene
  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

• Access to 3-arylmethyl-5-(methylthio)isoxazoles via an initial ring-opening of 2-methylthio-4-nitrothiophene
  作者：Lara Bianchi、Carlo Dell'Erba、Antonella Gabellini、Marino Novi、Giovanni Petrillo、Cinzia Tavani

  DOI：10.1016/s0040-4020(02)00292-2

  日期：2002.4

  The reactions of 1, 1 -bis(methylthio)-3-nitro-4-pyrrolidino-1.3-butadiene (deriving from the initial ring-opening of 2-methylthio-4-nitrothiophene with pyrrolidine and silver nitrate in EtOH) with arylmagnesium bromides result in the chemoselective replacement of the pyrrolidino group with the aryl moiety of the Grignards. The 4-aryl-1,1-bis(methylthio)-3-nitro-1,3-butadienes thus obtained are the key intermediates for the effective synthesis, through the corresponding reduction products 4-aryl-3-hydroximino-1, 1-bis(methylthio)-1-butenes, of the previously unknown 3-arylmethyl-5-(methylthio)isoxazoles. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.