1,2,3-triphenyl-3-ethynylcyclopropene | 108768-71-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2,3-triphenyl-3-ethynylcyclopropene
• 英文别名: 3-ethynyl-1,2,3-triphenylcyclopropene；1,1',1''-(3-Ethynylcycloprop-1-ene-1,2,3-triyl)tribenzene；(1-ethynyl-2,3-diphenylcycloprop-2-en-1-yl)benzene
• CAS: 108768-71-4
• 化学式: C₂₃H₁₆
• 分子量: 292.38
• InChiKey: DQNSBLCUWZBGOO-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C(Solv: hexane (110-54-3))
• 沸点：
  376.2±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2,3-triphenyl-3-ethynylcyclopropene 以 various solvent(s) 为溶剂， 反应 2.0h， 以26%的产率得到1,2-diphenyl-3-ethynyl-1H-indene
  参考文献：
  名称：

  An unusually robust triple bond: synthesis, structure and reactivity of 3-alkynylcyclopropenes

  摘要：

  Several 1,2-diphenyl- and 1,2,3-triphenyl-3-alkynylcyclopropenes have been prepared in moderate to very good yields by the reaction of acetylenic nucleophiles with the appropriate cyclopropenylium salt. Single crystal X-ray structures of four of the cyclopropenes were obtained. Stereoselective reduction of the triple bond failed in all cases, whereas model compounds lacking the cyclopropene moiety were reduced successfully. A rational for this lack of reactivity is proposed. The solution-phase thermochemistry of the 3-alkynyl-1,2,3-triphenylcyclopropenes was explored, affording 3-alkynyl-1H-indenes in moderate to good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.074
• 作为产物：
  描述：

  (1-溴-2,3-二苯基-1-环丙并-2-烯基)苯 在 乙基溴化镁 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 21.5h， 生成 1,2,3-triphenyl-3-ethynylcyclopropene
  参考文献：
  名称：

  An unusually robust triple bond: synthesis, structure and reactivity of 3-alkynylcyclopropenes

  摘要：

  Several 1,2-diphenyl- and 1,2,3-triphenyl-3-alkynylcyclopropenes have been prepared in moderate to very good yields by the reaction of acetylenic nucleophiles with the appropriate cyclopropenylium salt. Single crystal X-ray structures of four of the cyclopropenes were obtained. Stereoselective reduction of the triple bond failed in all cases, whereas model compounds lacking the cyclopropene moiety were reduced successfully. A rational for this lack of reactivity is proposed. The solution-phase thermochemistry of the 3-alkynyl-1,2,3-triphenylcyclopropenes was explored, affording 3-alkynyl-1H-indenes in moderate to good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.074

文献信息

• Domnin, I. N.; Ivanov, A. L.; Favorskaya, I. A., Journal of Organic Chemistry USSR (English Translation), 1986, p. 1599 - 1601
  作者：Domnin, I. N.、Ivanov, A. L.、Favorskaya, I. A.

  DOI：——

  日期：——
• DOMNIN I. N.; IVANOV A. L.; FAVORSKAYA I. A., ZH. ORGAN. XIMIYA, 22,(1986) N 8, 1780-1783
  作者：DOMNIN I. N.、 IVANOV A. L.、 FAVORSKAYA I. A.

  DOI：——

  日期：——
• An unusually robust triple bond: synthesis, structure and reactivity of 3-alkynylcyclopropenes
  作者：Robert D Gilbertson、He-Ping Wu、Drew Gorman-Lewis、Timothy J.R Weakley、Hans-Christoph Weiss、Roland Boese、Michael M Haley

  DOI：10.1016/j.tet.2003.11.074

  日期：2004.1

  Several 1,2-diphenyl- and 1,2,3-triphenyl-3-alkynylcyclopropenes have been prepared in moderate to very good yields by the reaction of acetylenic nucleophiles with the appropriate cyclopropenylium salt. Single crystal X-ray structures of four of the cyclopropenes were obtained. Stereoselective reduction of the triple bond failed in all cases, whereas model compounds lacking the cyclopropene moiety were reduced successfully. A rational for this lack of reactivity is proposed. The solution-phase thermochemistry of the 3-alkynyl-1,2,3-triphenylcyclopropenes was explored, affording 3-alkynyl-1H-indenes in moderate to good yields. (C) 2003 Elsevier Ltd. All rights reserved.