1,3-dimethylbenzindene-1-carboxylic acid | 132733-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-dimethylbenzindene-1-carboxylic acid
• 英文别名: 1,3-dimethylcyclopenta[b]naphthalene-3-carboxylic acid
• CAS: 132733-56-3
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: VKKOJOCFSGWPOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,3-dimethylbenzindene-1-carboxylic acid 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 4-(dimethylamino)pyridine hydrochloride 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 (-)-1,3-dimethylbenzindene-1-carbaldehyde
  参考文献：
  名称：

  1,5-Sigmatropic formyl migration in 1,3-dimethylbenz[f]indene-1-carbaldehyde; evidence for product-like transition states

  摘要：

  The title compound 1 has been prepared in an optically active form via a convenient seven-step sequence. The migratory ability of the formyl group allows the 1,5-shift 1 (arrows) involving disruption of naphthalene aromaticity to proceed with modest activation [DELTA-G double-ended dagger = 31.84 +/- 0.6 kcal mol-1 (145-degrees-C)]. Activation enthalpies for 1,5-formyl migration in 1, 3, 4 and 5 correlate well with changes in pi-electron energy in going from these compounds to their respective rearrangement products. Product-like transition states involving important cleavage of the bond between the migration origin and the formyl group are suggested for these rearrangements.

  DOI：

  10.1039/p19900003271
• 作为产物：
  描述：

  1,3-dimethylbenzindan-2-ol 在 正丁基锂 、 四溴化碳 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 甲苯 、 苯 为溶剂， 反应 5.08h， 生成 1,3-dimethylbenzindene-1-carboxylic acid
  参考文献：
  名称：

  1,5-Sigmatropic formyl migration in 1,3-dimethylbenz[f]indene-1-carbaldehyde; evidence for product-like transition states

  摘要：

  The title compound 1 has been prepared in an optically active form via a convenient seven-step sequence. The migratory ability of the formyl group allows the 1,5-shift 1 (arrows) involving disruption of naphthalene aromaticity to proceed with modest activation [DELTA-G double-ended dagger = 31.84 +/- 0.6 kcal mol-1 (145-degrees-C)]. Activation enthalpies for 1,5-formyl migration in 1, 3, 4 and 5 correlate well with changes in pi-electron energy in going from these compounds to their respective rearrangement products. Product-like transition states involving important cleavage of the bond between the migration origin and the formyl group are suggested for these rearrangements.

  DOI：

  10.1039/p19900003271

文献信息

• JONES, DAVID W.;MARMON, ROBERT J., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N2, C. 3271-3275
  作者：JONES, DAVID W.、MARMON, ROBERT J.

  DOI：——

  日期：——