bicyclo<4.3.0>nona-3,6-diene | 71436-04-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: bicyclo<4.3.0>nona-3,6-diene
• 英文别名: 1,2,4,7,7a-pentahydroindene；cis-Bicyclo<4,3,0>nona-3,7-dien；Bicyclo<4.3.0>nona-3,6-dien；cis-Bicyclo[4,3,0]nona-3,7-dien；Bicyclo[4.3.0]nona-3,6-diene；2,4,7,7a-tetrahydro-1H-indene
• CAS: 71436-04-9
• 化学式: C₉H₁₂
• 分子量: 120.194
• InChiKey: TVIGLDVLDQCMCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  cis-5,6-dichlorospiro[bicyclo[2.2.1]-hept-2-ene-7,1'-cyclopropane] 在 (4,4'-dimethyl-2,2'-bipyridine)PtPh(NTf2) 、 氨 、 sodium 作用下， 以 邻二氯苯 为溶剂， 反应 2.59h， 生成 bicyclo<4.3.0>nona-3,6-diene
  参考文献：
  名称：

  Pt-Catalyzed C–C Activation Induced by C–H Activation

  摘要：

  The catalytic cleavage of two C-C single bonds is achieved by treatment of the hydrocarbon substrate spiro[bicyclo[2.2.1]hept-2-ene-7,1'-cyclopropane] with Pt(II) catalysts such as (Me(2)bpy)PtPh(NTf2) (Me(2)bpy = 4,4'dimethyl-2,2'-bipyridine, NTf2- = N(SO2CF3)(2)(-)). The surprising rearrangement product 1,2,4,7,7a-pentahydroindene is generated in good yield. The mechanism of C-C bond activation is investigated using NMR spectroscopy, electrospray ionization mass spectrometry, and deuterium labeling, along with density functional theory calculations. These studies support an unusual catalytic mechanism in which an initial masked C-H bond activation initiates successive C-C bond cleavage events.

  DOI：

  10.1021/ja406260j

文献信息

• Nigmatova, V. B.; Zaitsev, Yu. V.; Anfilogova, S. N., Russian Journal of Organic Chemistry, 1994, vol. 30, # 5.1, p. 727 - 732
  作者：Nigmatova, V. B.、Zaitsev, Yu. V.、Anfilogova, S. N.、Pekhk, T. I.、Belikova, N. A.

  DOI：——

  日期：——
• New synthetic approach to 4-alkylidenecyclohexenes. Reduction-protodesilylation of benzylsilanes
  作者：Daniel J. Coughlin、Robert G. Salomon

  DOI：10.1021/jo01336a009

  日期：1979.10
• COUGHLIN D. J.; SALOMON R. G., J. ORG. CHEM., 1979, 44, NO 22, 3784-3790
  作者：COUGHLIN D. J.、 SALOMON R. G.

  DOI：——

  日期：——
• GEVORKYAN, G. G.;BELIKOVA, N. A.;BOBYLEVA, A. A.;PEXK, T. I.;ANFILOGOVA, +, ZH. ORGAN. XIMII, 1985, 21, N 8, 1732-1738
  作者：GEVORKYAN, G. G.、BELIKOVA, N. A.、BOBYLEVA, A. A.、PEXK, T. I.、ANFILOGOVA, +

  DOI：——

  日期：——
• Pt-Catalyzed C–C Activation Induced by C–H Activation
  作者：Miriam A. Bowring、Robert G. Bergman、T. Don Tilley

  DOI：10.1021/ja406260j

  日期：2013.9.4

  The catalytic cleavage of two C-C single bonds is achieved by treatment of the hydrocarbon substrate spiro[bicyclo[2.2.1]hept-2-ene-7,1'-cyclopropane] with Pt(II) catalysts such as (Me(2)bpy)PtPh(NTf2) (Me(2)bpy = 4,4'dimethyl-2,2'-bipyridine, NTf2- = N(SO2CF3)(2)(-)). The surprising rearrangement product 1,2,4,7,7a-pentahydroindene is generated in good yield. The mechanism of C-C bond activation is investigated using NMR spectroscopy, electrospray ionization mass spectrometry, and deuterium labeling, along with density functional theory calculations. These studies support an unusual catalytic mechanism in which an initial masked C-H bond activation initiates successive C-C bond cleavage events.