4-(2-ethylphenyl)-4-aza-tricyclo<5.2.1.0.2.6>dec-8-ene-2,5-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(2-ethylphenyl)-4-aza-tricyclo<5.2.1.0.2.6>dec-8-ene-2,5-dione
• 英文别名: 2-(2-ethylphenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione；(1S,2R,6S,7R)-4-(2-ethylphenyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: MNVLCOCLLWYUSW-CUFDPUGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙基苯胺 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-(2-ethylphenyl)-4-aza-tricyclo<5.2.1.0.2.6>dec-8-ene-2,5-dione
  参考文献：
  名称：

  Rotational features of carbon-nitrogen bonds in N-aryl maleimides. Atroposelective reactions of o-tert-butylphenylmaleimides

  摘要：

  Atroposelective addition and cycloaddition reactions of N-2-(tert-butylphenyl)- and N-2,5-(di-tert-butylphenyl)maleimide and a substituted derivative have been studied. Good to excellent stereoselectivities are generally observed, and high rotation barriers (about 29 kcal/mol) prevent the products from interconverting. Crystal structures of the precursors and products support a straight forward model where reactants attack trans to the o-tert-butyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00237-9

文献信息

• Transition-State Stabilization by n→π* Interactions Measured Using Molecular Rotors
  作者：Erik C. Vik、Ping Li、Perry J. Pellechia、Ken D. Shimizu

  DOI：10.1021/jacs.9b08542

  日期：2019.10.23

  A series of 16 molecular rotors were synthesized to investigate the ability of n→π* interactions to stabilize transition states (TS) of bond rotation. Steric contributions to the rotational barrier were isolated using control rotors, which could not form n→π* interactions. Rotors with strong acceptor π* orbitals such as ketones, aldehydes, and nitriles had greatly increased rates of rotation. The TS

  合成了一系列 16 个分子转子以研究 n→π* 相互作用稳定键旋转过渡态 (TS) 的能力。使用无法形成 n→π* 相互作用的控制转子隔离对旋转屏障的空间贡献。具有强受体 π* 轨道（如酮、醛和腈）的转子的旋转速率大大提高。高达 ~10 kcal/mol 的 TS 稳定性与在平面 TS 中酰亚胺羰基氧和邻-R 基团之间形成强的 n→π* 稳定性是一致的。计算研究有效地模拟了 TS 的稳定性和几何形状，NBO 分析证实了 n→π* 相互作用在稳定 TS 中的作用。
• Experimental Study of the Cooperativity of CH−π Interactions
  作者：Chen Zhao、Ping Li、Mark D. Smith、Perry J. Pellechia、Ken D. Shimizu

  DOI：10.1021/ol5014729

  日期：2014.7.3

  A series of new torsional molecular balances was designed to study the cooperativity of CH-pi interaction in the solid state and in solution. The measured interaction energies correlated better to the number of participating alkyl carbons than to the number of CH-pi contacts. The methyl and ethyl groups displayed additive interaction energies. However, the branched isopropyl group displayed strong positive cooperativity with higher than predicted interaction energies.