meso-1,5-dihydroxy-2,4-diphenylpentane | 13307-69-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: meso-1,5-dihydroxy-2,4-diphenylpentane
• 英文别名: 2,4-Diphenyl-2,4-pentandiol；rac.-β-2.4-Diphenyl-pentandiol-(2.4)；rac.-α-2.4-Diphenyl-pentandiol-(2.4)；2,4-diphenylpentane-2,4-diol
• CAS: 13307-69-2；20698-76-4；20698-77-5；32187-85-2
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: YAOJGXOSRNJYTN-IAGOWNOFSA-N

物化性质

• 沸点：
  426.9±40.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  二苯甲酰基甲烷 以 乙醚 为溶剂， 生成 meso-1,5-dihydroxy-2,4-diphenylpentane
  参考文献：
  名称：

  Studies in stereochemistry. XXXVIII. Open-chain vs. cyclic models for 1,3-asymmetric induction in addition reactions

  摘要：

  DOI：

  10.1021/ja01017a019

文献信息

• Direct Synthesis of <i>anti</i>-1,3-Diols through Nonclassical Reaction of Aryl Grignard Reagents with Isopropenyl Acetate
  作者：Yinchun Jiao、Chenzhong Cao、Zaichun Zhou

  DOI：10.1021/ol102520y

  日期：2011.1.21

  A series of symmetrical aromatic 1,3-diols were efficiently synthesized from substituted aryl Grignard reagents and isopropenyl acetate in a one-step reaction that formed anti products as the major species. Both experimental and theoretical studies suggested that the reaction involves the formation of a relatively stable intermediate E containing a six-membered ring from intermediate A. The stereoselectivity

  由取代的芳基格氏试剂和乙酸异丙烯酯有效地合成了一系列对称的芳香族1,3-二醇，它们一步形成了反产物，成为主要物质。实验和理论研究均表明，该反应涉及从中间体A形成相对稳定的中间体E，该中间体E包含六元环。反应的立体选择性和产物的分子结构通过NMR光谱，X射线衍射和气相色谱法确认。
• Action des organomagnésiens sur les composés β-dicarbonylés V. Synthèses de β-diols bitertiaires à partir de β-hydroxycétones. Induction asymétrique 1-3
  作者：Jacqueline Michel、Perséphone Canonne

  DOI：10.1139/v71-677

  日期：1971.12.15

  Addition of organomagnesium compounds to β-hydroxyketones with an asymmetric center gave a diastereoisomeric mixture of symmetric ditertiary β-diols, the ratio of meso and threo forms depending on the nature of the inductive group.The configurations of the β-diols were determined using their respective n.m.r. spectra in which the methyl and the methylene protons have different chemical shifts.The conformations of the β-hydroxyketones and the β-diols were studied by i.r. spectroscopy. Models for a preferred attack of the organomagnesium compounds are proposed and product-determining transition states for the reactions are also suggested.

  有机镁化合物加到具有不对称中心的β-羟基酮中，形成对映异构体混合物，对称的二叔丁基β-二醇，meso和threo形式的比例取决于电子诱导基团的性质。通过它们各自的n.m.r.谱图确定了β-二醇的构型，其中甲基和亚甲基质子具有不同的化学位移。通过i.r.光谱研究了β-羟基酮和β-二醇的构象。提出了有机镁化合物优先攻击的模型，并推荐了反应的产物确定过渡态。