(1S,2S)-4,6-Diethyl-1-methyl-2-phenyl-indan-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S,2S)-4,6-Diethyl-1-methyl-2-phenyl-indan-2-ol
• 英文别名: (1S,2S)-4,6-diethyl-1-methyl-2-phenyl-1,3-dihydroinden-2-ol
• 化学式: C₂₀H₂₄O
• 分子量: 280.41
• InChiKey: GXDCJAUJQOAACG-XOBRGWDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  α-(2,4,6-Triethylphenyl)acetophenone 以 氘代甲醇 为溶剂， 生成 (1R,2S)-4,6-Diethyl-1-methyl-2-phenyl-indan-2-ol 、 (1S,2S)-4,6-Diethyl-1-methyl-2-phenyl-indan-2-ol
  参考文献：
  名称：

  High diastereoselectivity in the cyclization of 1,5-biradicals: what causes such sizeable steric barriers to biradical coupling?

  摘要：

  The high diastereoselectivities observed in the photocyclization of alpha-(o-ethylphenyl)acetophenones appear to reflect conformational equilibria in the triplet 1,5-biradical intermediates rather than steric barriers created during cyclization. The necessary biradical triplet-->singlet intersystem crossing is proposed to occur along the cyclization reaction coordinate since the orthogonality of the two singly-occupied p orbitals does not depress biradical lifetimes.

  DOI：

  10.1016/0040-4039(91)80844-v

文献信息

• High diastereoselectivity in the cyclization of 1,5-biradicals: what causes such sizeable steric barriers to biradical coupling?
  作者：Peter J. Wagner、Bong Ser Park

  DOI：10.1016/0040-4039(91)80844-v

  日期：1991.1

  The high diastereoselectivities observed in the photocyclization of alpha-(o-ethylphenyl)acetophenones appear to reflect conformational equilibria in the triplet 1,5-biradical intermediates rather than steric barriers created during cyclization. The necessary biradical triplet-->singlet intersystem crossing is proposed to occur along the cyclization reaction coordinate since the orthogonality of the two singly-occupied p orbitals does not depress biradical lifetimes.
• Entropy <i>vs</i> Enthalpy Control of 1,5-Biradical Cyclization in the Photochemistry of α-(<i>o</i>-Alkylphenyl)acetophenones
  作者：Peter J. Wagner、Ali Zand、Bong-Ser Park

  DOI：10.1021/ja962683h

  日期：1996.1.1