4-N-dimethylaminobutyn-2-yl ester of benzoic acid | 38697-68-6

• 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: 4-N-dimethylaminobutyn-2-yl ester of benzoic acid
• 英文别名: 4-(dimethylamino)but-2-ynyl benzoate；1-benzoyloxy-4-dimethylamino-but-2-yne；1-Benzoyloxy-4-dimethylamino-but-2-in；γ-(N-Dimethylamino)methylpropargylbenzoat；2-Butyn-1-ol, 4-(dimethylamino)-, benzoate (ester)
• CAS: 38697-68-6
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: RFWSKQOCEPHONN-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  155 °C(Press: 2 Torr)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四甲基乙二胺 、 苯酸炔丙酯 在 叔丁基过氧化氢 、 copper dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以77%的产率得到4-N-dimethylaminobutyn-2-yl ester of benzoic acid
  参考文献：
  名称：

  Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation: C–H versus C–C cleavage in TMEDA

  摘要：

  Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation reactions have been achieved under facile and mild conditions. TMEDA coupled with various terminal alkynes via C-H bond cleavage in good yields using atmospheric oxygen as an oxidant. Switching from air to TBHP afforded aminomethylation products of terminal alkynes through C-C bond cleavage of TMEDA. The protocol provided a novel strategy to prepare bi/tridentate N-ligand. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.118

文献信息

• Synthesis and antiinflammatory activity of aminoacetylenic esters of benzoic acids
  作者：A. D. Dzhuraev、A. G. Makhsumov、U. B. Zakirov、A. T. Nikbaev、K. Karimkulov

  DOI：10.1007/bf00766472

  日期：1990.8
• Marszak et al., Memorial des services chimiques de l'Etat, 1951, vol. 36, p. 411,413
  作者：Marszak et al.

  DOI：——

  日期：——
• DZHURAEV, A. D.;MAXSUMOV, A. G.;ZAKIROV, U. B.;NIKBAEV, A. T.;KARIMKULOV,+, XIM.-FARMATS. ZH., 24,(1990) N, S. 30-31
  作者：DZHURAEV, A. D.、MAXSUMOV, A. G.、ZAKIROV, U. B.、NIKBAEV, A. T.、KARIMKULOV,+

  DOI：——

  日期：——
• Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation: C–H versus C–C cleavage in TMEDA
  作者：Qi Shen、Lei Zhang、Yu-Ren Zhou、Jian-Xin Li

  DOI：10.1016/j.tetlet.2013.09.118

  日期：2013.12

  Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation reactions have been achieved under facile and mild conditions. TMEDA coupled with various terminal alkynes via C-H bond cleavage in good yields using atmospheric oxygen as an oxidant. Switching from air to TBHP afforded aminomethylation products of terminal alkynes through C-C bond cleavage of TMEDA. The protocol provided a novel strategy to prepare bi/tridentate N-ligand. (C) 2013 Elsevier Ltd. All rights reserved.