3-methylbuta-1,3-dien-1-yl 4-nitrobenzoate

• 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: 3-methylbuta-1,3-dien-1-yl 4-nitrobenzoate
• 英文别名: [(1Z)-3-methylbuta-1,3-dienyl] 4-nitrobenzoate
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: WDWHPMXMPYRDIM-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-溴-2-甲基-1-丙烯 、 4-硝基苯甲酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 叔丁基锂 、 4-二甲氨基吡啶 作用下， 以 乙醚 、 正戊烷 、 二氯甲烷 为溶剂， 以9%的产率得到2-methyl-3-butyl-2-yl 4-nitrobenzoate
  参考文献：
  名称：

  A [3.3]Sigmatropic Rearrangement of α,β-Unsaturated Fischer Chromium Carbenes: Synthesis of Alkynol and Dienol Esters

  摘要：

  A novel [3.3]sigmatropic rearrangement of in situ formed alpha,beta-unsaturated Fischer acyloxy carbenes forming alkynol esters is described. For example, reaction of tetramethylammonium pentacarbonyl(1-oxo-2-butenyl)chromate(1-) (4) with 4-methoxybenzoyl chloride gave 2-methyl-3-butyn-2-yl 4-methoxybenzoate (8) in 32% yield. In addition to the rearrangement products, dienol esters formed by a formal beta-hydride elimination-reductive elimination sequence were usually isolated. In the above example, 3-methylbuta-1,3-dien-1-yl 4-methoxybenzoate (9) was obtained (16%) as the side product. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00216-7

文献信息

• A [3.3]Sigmatropic Rearrangement of α,β-Unsaturated Fischer Chromium Carbenes: Synthesis of Alkynol and Dienol Esters
  作者：Björn C. Söderberg、Shannon N. O'Neil、Angela C. Chisnell、Jian Liu

  DOI：10.1016/s0040-4020(00)00216-7

  日期：2000.7

  A novel [3.3]sigmatropic rearrangement of in situ formed alpha,beta-unsaturated Fischer acyloxy carbenes forming alkynol esters is described. For example, reaction of tetramethylammonium pentacarbonyl(1-oxo-2-butenyl)chromate(1-) (4) with 4-methoxybenzoyl chloride gave 2-methyl-3-butyn-2-yl 4-methoxybenzoate (8) in 32% yield. In addition to the rearrangement products, dienol esters formed by a formal beta-hydride elimination-reductive elimination sequence were usually isolated. In the above example, 3-methylbuta-1,3-dien-1-yl 4-methoxybenzoate (9) was obtained (16%) as the side product. (C) 2000 Elsevier Science Ltd. All rights reserved.