cis-1-methyl-2-phenylcyclobutane-1,2-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-1-methyl-2-phenylcyclobutane-1,2-diol
• 英文别名: (1S,2S)-1-methyl-2-phenylcyclobutane-1,2-diol
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: GLXJZSAIFIJHHZ-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基-1,4-戊二酮 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以88%的产率得到cis-1-methyl-2-phenylcyclobutane-1,2-diol
  参考文献：
  名称：

  io二碘化物介导的1,4-二酮-I的松酸酯化。稠合的单，双和三环环丁烷-1,2-二醇的立体选择性合成

  摘要：

  标题反应已经以良好的产率应用于各种顺式-环丁烷-1,2-二醇的合成中。

  DOI：

  10.1016/0040-4020(96)00687-4

文献信息

• Electroreductive crossed pinacol coupling of aromatic ketones with aliphatic ketones and aldehydes
  作者：Naoki Kise、Yousuke Shiozawa、Nasuo Ueda

  DOI：10.1016/j.tet.2007.04.050

  日期：2007.6

  The intermolecular crossed pinacol coupling of aromatic ketones with aliphatic aldehydes and ketones was effected by electroreduction in the presence of chlorotrimethylsilane. The best result was obtained using a Pb cathode in Bu4NPF6/THF. The electroreduction of aromatic 1,4-, 1,5-, and 1,6-diketones under the same conditions gave four-, five-, and six-membered 1,2-diols with trans-stereoselectivity

  芳族酮与脂族醛和酮的分子间交叉频哪醇偶联是在氯代三甲基硅烷存在下通过电还原实现的。使用Bu 4 NPF 6 / THF中的Pb阴极可获得最佳结果。在相同条件下电还原芳族1,4-，1,5-和1,6-二酮可得到具有反式立体选择性的四元，五元和六元1,2-二醇TiCl 4 -Zn的二酮主要产生相同分子内交叉频哪醇偶联产物的顺式异构体。
• Unexpected Ti^III/Mn-Promoted Pinacol Coupling of Ketones
  作者：Miguel Paradas、Araceli G. Campaña、Rosa E. Estévez、Luis Álvarez de Cienfuegos、Tania Jiménez、Rafael Robles、Juan M. Cuerva、J. Enrique Oltra

  DOI：10.1021/jo9005238

  日期：2009.5.1

  Titanocene(III) chemistry has emerged in the last decades as an indispensable tool in C-C bond-forming reactions. In this context, pinacol and related reactions allow the stereoselective synthesis of vicinal diols. In this work, we present new applications of these reactions using as starting materials aromatic ketones. Simple and smooth reaction conditions have been developed and have been applied for inter- and intramolecular processes. We also describe that although Cp2TiCl is usually used as a monoelectronic reducing agent, it can be also used as an efficient Lewis acid.
• trans-Stereoselective intramolecular crossed pinacol coupling of aromatic 1,4-, 1,5-, and 1,6-diketones by electroreduction
  作者：Naoki Kise、Yousuke Shiozawa、Nasuo Ueda

  DOI：10.1016/j.tetlet.2004.08.120

  日期：2004.10

  Electroreduction of aromatic 1,4-, 1,5-, and 1,6-diketones in the presence of chlorotrimethylsilane and triethylamine gave four-, five-, and six-membered 1,2-diols with trans-stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.