(2R^*,3S^*,4R^*)-2-methyl-4-phenylpentane-1,3-diol | 124508-30-1

• 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: (2R^*,3S^*,4R^*)-2-methyl-4-phenylpentane-1,3-diol
• 英文别名: (2SR,3RS,4SR)-2-methyl-4-phenylpentane-1,3-diol；(2S,3R,4S)/(2R,3S,4R)-2-methyl-4-phenylpentane-1,3-diol；(2S,3R,4S)-2-methyl-4-phenylpentane-1,3-diol
• CAS: 124508-30-1
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: QHHHOANTQPBUAH-NHCYSSNCSA-N

物化性质

• 沸点：
  334.6±30.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  在 lithium aluminium tetrahydride 作用下， 生成 (2R^*,3S^*,4R^*)-2-methyl-4-phenylpentane-1,3-diol
  参考文献：
  名称：

  Ni-Catalyzed Borylative Diene−Aldehyde Coupling: The Remarkable Effect of P(SiMe₃)₃

  摘要：

  The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. In the presence of P(SiMe3)(3), this reductive coupling furnishes allyl boronic esters which are regioisomeric to those obtained with PCy3 as the ligand. The coupling product may be subject to oxidation, which furnishes the derived 1,3-diol, or allytation with an additional aldehyde, which furnishes the derived 1,6-diol in a stereoselective fashion.

  DOI：

  10.1021/ja101513d

文献信息

• Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters
  作者：Cesare Gennari、Anna Bernardi、Silvia Cardani、Carlo Scolastico

  DOI：10.1016/0040-4020(84)85086-3

  日期：1984.1

  dialkoxyboranes derived from thioesters were found to be stereoconvergent: both Z and E enolates give syn aldol condensation products. The thioester additions to chiral aldehydes were studied. Internal selectivity (syn) was usually very high, while the relative stereoselectivity ranged from poor to good, depending on the specific aldehyde used. The aldol products were transformed to known compounds for correlation

  进行了详细的研究，将硫代丙酸苯基酯与亚乙基氯硼酸酯（ECB）和二异丙基乙胺（DPEA）进行烯醇化，随后对这些烯醇化物进行醇醛缩合反应。已发现衍生自硫酯的烯氧基二烷氧基硼烷是立体收敛的：Z和E的烯醇盐均生成顺式醇醛缩合产物。研究了手性醛中硫代酯的添加。内部选择性（syn）通常很高，而相对的立体选择性则根据所使用的特定醛的不同，从差到好。将醛醇缩合产物转化为已知化合物以进行相关。
• Acyclic stereoselection. 50. New stereoselective propanal/propanoic acid synthons for aldol reactions
  作者：Ichiro Mori、Kazuaki Ishihara、Clayton H. Heathcock

  DOI：10.1021/jo00290a060

  日期：1990.2