(E)-3-azido-2-(3-phenylprop-2-ynylidene)cyclohexanone | 1228932-15-7

• 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)-3-azido-2-(3-phenylprop-2-ynylidene)cyclohexanone
• 英文别名: (2E)-3-azido-2-(3-phenylprop-2-ynylidene)cyclohexan-1-one
• CAS: 1228932-15-7
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: HPAZSIAXWSFOCT-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-azido-2-(3-phenylprop-2-ynylidene)cyclohexanone 以 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到3-phenyl-7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-one
  参考文献：
  名称：

  3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita–Baylis–Hillman adducts of propargyl aldehydes

  摘要：

  A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxy carbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.017
• 作为产物：
  描述：

  2-(1-acetoxy-3-phenylprop-2-yn-1-yl)cyclohex-2-enone 在 sodium azide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以83%的产率得到(E)-3-azido-2-(3-phenylprop-2-ynylidene)cyclohexanone
  参考文献：
  名称：

  3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita–Baylis–Hillman adducts of propargyl aldehydes

  摘要：

  A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxy carbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.017

文献信息

• Oxidative Aza-Annulation of Enynyl Azides to 2-Keto/Formyl-1<i>H</i>-pyrroles
  作者：Chada Raji Reddy、Sujatarani A. Panda、Andhavaram Ramaraju

  DOI：10.1021/acs.joc.6b02468

  日期：2017.1.20

  the intramolecular oxidative aza-annulation of enynyl azides is reported for the first time. It involves a sequential carbon–nitrogen/carbon–oxygen bond formations, and the combination of AuCl3 with AgSbF6 was identified as a suitable reagent system to promote the present reaction. The required enynyl azides are readily prepared from Morita–Baylis–Hillman (MBH) acetates of acetylenic aldehydes.

  首次报道了通过烯丙基叠氮化物的分子内氧化氮杂-环化反应构造带有2-酮或甲酰基的吡咯的方法。它涉及顺序的碳-氮/碳-氧键形成，AuCl 3和AgSbF 6的结合被确定为促进本反应的合适试剂系统。所需的烯丙基叠氮化物可以从炔属醛的Morita–Baylis–Hillman（MBH）乙酸酯中轻松制备。
• 3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita–Baylis–Hillman adducts of propargyl aldehydes
  作者：Sun Pil Park、Sang-Hyun Ahn、Kee-Jung Lee

  DOI：10.1016/j.tet.2010.03.017

  日期：2010.5

  A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxy carbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed. (C) 2010 Elsevier Ltd. All rights reserved.