(Z)-1-Methyl-2-phenyl-2-indanol | 128517-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (Z)-1-Methyl-2-phenyl-2-indanol
• 英文别名: (1S,2R)-1-methyl-2-phenyl-1,3-dihydroinden-2-ol
• CAS: 128517-15-7
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: CJTIWPLAKOZKEO-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(2-甲基苯基)苯乙酮 在 sodium hydride 作用下， 反应 13.0h， 生成 (Z)-1-Methyl-2-phenyl-2-indanol
  参考文献：
  名称：

  Wagner, Peter J.; Zhou, Boli; Hasegawa, Tadashi, Journal of the American Chemical Society, 1991, vol. 113, # 25, p. 9640 - 9654

  摘要：

  DOI：

文献信息

• Efficient solid state photocyclization of sterically congested α-o-tolyl ketones despite “poor” geometries for hydrogen abstraction
  作者：Peter J. Wagner、Boli Zhou

  DOI：10.1016/s0040-4039(01)80575-x

  日期：1989.1

  Several α-mesityl and α-(o-tolyl)acetophenones undergo photocyclization to 2-indanols almost quantitatively when irradiated as crystals, even those that undergo significant competing α-cleavage or 1,3-aryl shift in solution. The requisite triplet δ-hydrogen abstraction apparently can occur at what appears to be a “bad” geometry. One ketone, α-(o-tolyl)propiophenone, partially rearranges to the β-isomer

  几种α-间苯二甲酰和α-（邻甲苯基）苯乙酮以晶体辐射时几乎定量地发生光环化成2-茚满醇，即使那些在溶液中经历显着竞争的α-裂解或1,3-芳基转移的化合物也是如此。必要的三重态δ-氢提取显然可以发生在看似“不良”的几何形状上。一种酮，α-（邻甲苯基）丙酮，部分重排为β-异构体，这是由最初的α-裂解形成的自由基歧化所致。
• Wagner, Peter J.; Meador, Michael A.; Zhou, Boli, Journal of the American Chemical Society, 1991, vol. 113, # 25, p. 9630 - 9639
  作者：Wagner, Peter J.、Meador, Michael A.、Zhou, Boli、Park, Bong-Ser

  DOI：——

  日期：——
• 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
• 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.
• Conformational Control of Product Ratios from Triplet 1,5-Biradicals
  作者：Ali Zand、Bong-Ser Park、Peter J. Wagner

  DOI：10.1021/jo962139r

  日期：1997.4.1