(-)-1-phenylethyl 1,3-dimethylbenzindene-1-carboxylate | 132733-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-1-phenylethyl 1,3-dimethylbenzindene-1-carboxylate
• CAS: 132733-57-4；132733-59-6
• 化学式: C₂₄H₂₂O₂
• 分子量: 342.437
• InChiKey: HHQYWQYMJSTDQR-KEJDIYNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-1-phenylethyl 1,3-dimethylbenzindene-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以89%的产率得到(-)-1-hydroxymethyl-1,3-dimethylbenzindene
  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 4-二甲氨基吡啶 、 正丁基锂 、 四溴化碳 、 4-(dimethylamino)pyridine hydrochloride 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.08h， 生成 (-)-1-phenylethyl 1,3-dimethylbenzindene-1-carboxylate
  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