2-methylbut-3-en-2-yl 4-nitrobenzoate | 35945-67-6

• 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: 2-methylbut-3-en-2-yl 4-nitrobenzoate
• 英文别名: 4-nitro-benzoic acid-(1,1-dimethyl-allyl ester)；4-Nitro-benzoesaeure-(1,1-dimethyl-allylester)；2-Methyl-3-buten-2-yl-p-nitrobenzoat；1,1-Dimethyl-2-propen-1-YL 4-nitrobenzoate
• CAS: 35945-67-6
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: WTGSWOHAWGARQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylbut-3-en-2-yl 4-nitrobenzoate 在 pyridinium hydrobromide perbromide 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 4-Nitro-benzoic acid 2,3-dibromo-1,1-dimethyl-propyl ester
  参考文献：
  名称：

  Novel One-Pot Method for Chemoselective Bromination and Sequential Sonogashira Coupling

  摘要：

  An efficient one-pot method for bromination-elimination of allyl alcohol derivatives and sequential Sonogashira coupling has been developed. A highlight of the method is chemoselective DBU-promoted elimination of vicinal dibromoalkanes having an adjacent O-functional group.

  DOI：

  10.1021/ol101110v
• 作为产物：
  描述：

  2-methyl-3-butyl-2-yl 4-nitrobenzoate 在 palladium-barium carbonate 、 乙酸乙酯 作用下， 生成 2-methylbut-3-en-2-yl 4-nitrobenzoate
  参考文献：
  名称：

  The Preparation of t-Acetylenic Carbinol Esters and Related Compounds¹

  摘要：

  DOI：

  10.1021/ja01566a032

文献信息

• One-Pot Method for Regioselective Bromin­ation and Sequential Carbon-Carbon Bond-Forming Reactions of Allylic Alcohol Derivatives
  作者：Noriki Kutsumura、Yusuke Matsubara、Kentaro Niwa、Ai Ito、Takao Saito

  DOI：10.1002/ejoc.201300173

  日期：2013.6

  An efficient one-pot method for the regioselective bromination of allylic alcohol derivatives (two-step reaction sequence) followed by Sonogashira, Negishi, or Suzuki–Miyaura coupling reactions in the same reaction vessel (three-step reaction sequence) has been developed. The key reaction in these one-pot systems is the regioselective DBU-promoted trans HBr elimination of vicinal dibromides bearing

  已经开发了一种有效的一锅法，用于烯丙醇衍生物的区域选择性溴化（两步反应顺序），然​​后在同一反应容器中进行 Sonogashira、Negishi 或 Suzuki-Miyaura 偶联反应（三步反应顺序）。这些一锅系统中的关键反应是区域选择性 DBU 促进的反式 HBr 消除带有相邻 O 官能团的邻位二溴化物。
• Straus; Kuehnel, Chemische Berichte, 1933, vol. 66, p. 1834,1839
  作者：Straus、Kuehnel

  DOI：——

  日期：——
• Iridium-Catalyzed Hydrocarboxylation of 1,1-Dimethylallene:  Byproduct-Free Reverse Prenylation of Carboxylic Acids
  作者：In Su Kim、Michael J. Krische

  DOI：10.1021/ol702914p

  日期：2008.2.1

  Exposure of carboxylic acids 1a-12a to commercially available 1,1-dimethylallene in the presence of substoichiometric quantities of an iridium catalyst prepared in situ from [ir(cod)Cl](2) and BIPHEP provides the corresponding 1,1-dimethylallyl (reverse prenyl) esters 1b-12b in 74-92% isolated yield. This protocol represents the first branch-regioselective allene hydrocarboxylation. Stoichiometric byproducts are not generated in this process and protecting groups are not required for alcohols, phenols, and indolic amines.
• Novel One-Pot Method for Chemoselective Bromination and Sequential Sonogashira Coupling
  作者：Noriki Kutsumura、Kentaro Niwa、Takao Saito

  DOI：10.1021/ol101110v

  日期：2010.8.6

  An efficient one-pot method for bromination-elimination of allyl alcohol derivatives and sequential Sonogashira coupling has been developed. A highlight of the method is chemoselective DBU-promoted elimination of vicinal dibromoalkanes having an adjacent O-functional group.
• The Preparation of t-Acetylenic Carbinol Esters and Related Compounds¹
  作者：G. F. Hennion、S. Olivia Barrett

  DOI：10.1021/ja01566a032

  日期：1957.5