(1S,2R,3R/1R,2S,3S)-3-cyclohexyl-2-methyl-1-phenyl-1,3-propanediol | 106565-25-7

• 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: (1S,2R,3R/1R,2S,3S)-3-cyclohexyl-2-methyl-1-phenyl-1,3-propanediol
• 英文别名: (1R*,2R*,3S*)-1-Cyclohexyl-2-methyl-3-phenylpropane-1,3-diol；rac-(1R,2R,3S)-1-cyclohexyl-2-methyl-3-phenylpropane-1,3-diol；(1S,2S,3R)-1-cyclohexyl-2-methyl-3-phenylpropane-1,3-diol
• CAS: 106565-25-7
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: VKRQCUFLQPZRMC-DAXOMENPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R/1R,2S,3S)-3-cyclohexyl-2-methyl-1-phenyl-1,3-propanediol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 生成 rac-(4R,5S,6S)-4-cyclohexyl-2,2,5-trimethyl-6-phenyl-[1.3]dioxane
  参考文献：
  名称：

  Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads

  摘要：

  Asymmetric aldol-Tishchenko, reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBU)(2)/Cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.

  DOI：

  10.1021/jo9003635
• 作为产物：
  描述：

  rac-(1R,2S,3S)-1-cyclohexyl-3-hydroxy-2-methyl-3-phenylpropyl cyclohexanecarboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (1S,2R,3R/1R,2S,3S)-3-cyclohexyl-2-methyl-1-phenyl-1,3-propanediol
  参考文献：
  名称：

  Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads

  摘要：

  Asymmetric aldol-Tishchenko, reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBU)(2)/Cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.

  DOI：

  10.1021/jo9003635

文献信息

• Stereospecific conversion of (1R*,3S*)- and (1R*,3R*)-3-cyclohexyl-1-phenylpropane-1,3-diol into the corresponding 2,4-disubstituted oxetanes
  作者：Tajassus Aftab、Christabel Carter、Martin Christlieb、Jennifer Hart、Adam Nelson

  DOI：10.1039/a909163g

  日期：——

  Conversion of two diastereoisomeric 1,3-diols (3-cyclohexyl-1-phenylpropane-1,3-diol) into orthoesters was followed by treatment with acetyl bromide. The 1,3-bromo acetates (acetic acid 3-bromo-1-cyclohexyl-3-phenylpropyl esters) were obtained with complete inversion of configuration at a benzylic site. Methanolysis of the bromo acetates, followed by ring-closure, resulted in a second inversion of configuration at a benzylic site to give the corresponding oxetanes with overall retention of configuration.

  将两个非对映异构体1,3-二醇（3-环己基-1-苯基丙烯-1,3-二醇）转化为邻醇酯，随后用溴乙酸酯处理。在苯基取代位点实现了完全的构型反转，得到了1,3-溴乙酸酯（乙酸3-溴-1-环己基-3-苯基丙基酯）。对溴乙酸酯进行甲醇解后，再进行环闭合，导致在苯基取代位点发生第二次构型反转，最终得到相应的氧环丁烷，并整体保留了构型。
• Chelation- and nonchelation-controlled reductions of .beta.-dicarbonyl compounds to 1,3-diols with three chiral centers
  作者：Jose Barluenga、Julio G. Resa、Bernardo Olano、Santos Fustero

  DOI：10.1021/jo00384a009

  日期：1987.4