cis-2-(4'-dimethylaminobenzyl)-1-indanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: cis-2-(4'-dimethylaminobenzyl)-1-indanol
• 英文别名: (1R,2R)-2-[[4-(dimethylamino)phenyl]methyl]-2,3-dihydro-1H-inden-1-ol
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: PXALMTFPPQCENJ-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-(dimethylamino)benzyl)-2,3-dihydro-1H-inden-1-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以52%的产率得到cis-2-(4'-dimethylaminobenzyl)-1-indanol
  参考文献：
  名称：

  Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of γ-arylalkanols

  摘要：

  AbstractA novel fragmentation reaction accompanied by the unidirectional migration of three hydrogen atoms has been found in the radical cations of γ‐arylpropanols with electron‐donating substituents in the para position. This triple hydrogen (3H) rearrangement reaction is the dominant fragmentation channel of the long‐lived molecular ions of trans‐2‐(4′‐dimethylaminobenzyl)‐l‐indanol, 2, but it occurs also in simpler γ‐arylpropanol ions. Deuterium labelling of 2 reveals that the three hydrogen atoms originate with extraordinarily high specificity from the C(l), C(2) and O positions of the alcohol moiety. Cis‐ and 3′‐substituted isomers do not undergo this reaction. Along with the 3H rearrangement reaction a unidirectional double hydrogen (2H) rearrangement reaction takes place independently and with less specificity in the trans‐2‐(4′‐X‐benzyl)‐l‐indanol ions 1+˙ and 2+˙. No hydrogen exchange occurs during the 3H and 2H rearrangement reactions. Mechanistic alternatives of these unusual fragmentation reactions are discussed; the experimental evidence strongly favours pathways via several intermediate ion–neutral complexes.

  DOI：

  10.1002/oms.1210230904

文献信息

• Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of γ-arylalkanols
  作者：Dietmar Kuck、Ulrich Filges

  DOI：10.1002/oms.1210230904

  日期：1988.9

  AbstractA novel fragmentation reaction accompanied by the unidirectional migration of three hydrogen atoms has been found in the radical cations of γ‐arylpropanols with electron‐donating substituents in the para position. This triple hydrogen (3H) rearrangement reaction is the dominant fragmentation channel of the long‐lived molecular ions of trans‐2‐(4′‐dimethylaminobenzyl)‐l‐indanol, 2, but it occurs also in simpler γ‐arylpropanol ions. Deuterium labelling of 2 reveals that the three hydrogen atoms originate with extraordinarily high specificity from the C(l), C(2) and O positions of the alcohol moiety. Cis‐ and 3′‐substituted isomers do not undergo this reaction. Along with the 3H rearrangement reaction a unidirectional double hydrogen (2H) rearrangement reaction takes place independently and with less specificity in the trans‐2‐(4′‐X‐benzyl)‐l‐indanol ions 1+˙ and 2+˙. No hydrogen exchange occurs during the 3H and 2H rearrangement reactions. Mechanistic alternatives of these unusual fragmentation reactions are discussed; the experimental evidence strongly favours pathways via several intermediate ion–neutral complexes.