1-[(1E)-3-methylbuta-1,3-dienyl]-4-nitrobenzene | 89510-63-4

• 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: 1-[(1E)-3-methylbuta-1,3-dienyl]-4-nitrobenzene
• CAS: 89510-63-4
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: DOGGROQPDVVIKH-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(1E)-3-methylbuta-1,3-dienyl]-4-nitrobenzene 在 dichlororuthenium(IV) meso-tetrakis(2,6-dichlorophenyl)porphyrin 2,6-二氯吡啶N-氧化物 作用下， 以 氘代氯仿 为溶剂， 反应 0.5h， 以90%的产率得到(E)-2-Methyl-4-(4-nitro-phenyl)-but-3-enal
  参考文献：
  名称：

  一种实用且温和的方法，用于通过钌（IV）-卟啉催化剂的环氧化异构化将末端烯烃高度选择性地转化为醛。

  摘要：

  DOI：

  10.1002/anie.200460545
• 作为产物：
  描述：

  1-[(1Z)-3-methylbuta-1,3-dienyl]-4-nitrobenzene 在 二氧化硫 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 1-[(1E)-3-methylbuta-1,3-dienyl]-4-nitrobenzene
  参考文献：
  名称：

  One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide

  摘要：

  2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization by classical means fails or leads to their polymerization. It is shown that SO, can isomerize 1-aryl-3-methyl-1.3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1.3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)-->(E) isomerizations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.070

文献信息

• MITSUDO, TAKI-AKI;FISCHETTI, W.;HECK, R. F., J. ORG. CHEM., 1984, 49, N 9, 1640-1646
  作者：MITSUDO, TAKI-AKI、FISCHETTI, W.、HECK, R. F.

  DOI：——

  日期：——
• US7582750B2
  申请人：——

  公开号：US7582750B2

  公开（公告）日：2009-09-01
• A Practical and Mild Method for the Highly Selective Conversion of Terminal Alkenes into Aldehydes through Epoxidation–Isomerization with Ruthenium(IV)–Porphyrin Catalysts
  作者：Jian Chen、Chi-Ming Che

  DOI：10.1002/anie.200460545

  日期：2004.9.20
• One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide
  作者：Srinivas Reddy Dubbaka、Pierre Vogel

  DOI：10.1016/j.tet.2004.11.070

  日期：2005.2

  2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization by classical means fails or leads to their polymerization. It is shown that SO, can isomerize 1-aryl-3-methyl-1.3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1.3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)-->(E) isomerizations. (C) 2004 Elsevier Ltd. All rights reserved.