9,10-bis(-2-pivalamidopropyl)-9,10-dihydroanthracene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(-2-pivalamidopropyl)-9,10-dihydroanthracene
• 英文别名: N-[1-[10-[2-(2,2-dimethylpropanoylamino)propyl]-9,10-dihydroanthracen-9-yl]propan-2-yl]-2,2-dimethylpropanamide
• 化学式: C₃₀H₄₂N₂O₂
• 分子量: 462.676
• InChiKey: GRCYRJOBZFMDSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-pivaloyl-2-methyl aziridine 在 蒽 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 N-n-propylpivaloylamide 、 9-(2-pivalamidopropyl)-10-(1-methyl-2-pivalamidoethyl)-9,10-dihydroanthracene 、 9,10-bis(-2-pivalamidopropyl)-9,10-dihydroanthracene 、 N-(5,5-dimethyl-4-oxohexan-2-yl)-2,2-dimethylpropanamide
  参考文献：
  名称：

  Lin, Pen-Yuan; Werry, Juergen; Bentz, Gunther, Journal of the Chemical Society. Perkin transactions I, 1993, # 10, p. 1139 - 1146

  摘要：

  DOI：

文献信息

• Aziridines. 59. Regioselectivity in nucleophilic Ring Opening of 2-Methylaziridines. Lag of bond making as model for the abnormal opening
  作者：Pen-Yuan Lin、Gunther Bentz、H. Stamm

  DOI：10.1002/prac.19933350105

  日期：——

  The regioselectivity ratio RS = normal : abnormal opening of activated 2-methylaziridines 2 by nucleophiles is found to range from 0.10 to unmeasurable large (only normal opening = substitution at CH2 by strongly basic carbanions). RS is assumed to result from S(N)2 variants differing in the degree to which bond breaking is ahead of bond making including perhaps synchronous S(N)2. Bond breaking will be more ahead for the N-CMe bond. High nucleophilic power pushes bond making toward a synchronous process resulting in great RS. The decrease in RS with acyl activation relative to sulfonyl activation is in accord with a flattening of the nitrogen pyramid (planarization effect). The planarization effect is retained in acidic medium by O-protonation: Rs 0.10 - 0.14 for methanolysis as compared to RS 0.43 for N-protonated sulfonylaziridine 2h. AM1 calculations support the planarization hypothesis. - No indication for SET with trityl anion was found.