(RS)-(+/-)-2,3-diphenyl-1,2-propanediol | 155203-78-4

• 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: (RS)-(+/-)-2,3-diphenyl-1,2-propanediol
• 英文别名: 2,3-diphenylpropane-1,2-diol；2,3-diphenyl-propane-1,2-diol；(+/-)-α-Hydroxy-α-hydroxymethyl-bibenzyl；α-Hydroxymethyl-bibenzylol-(α)；(+/-)-2.3-Dihydroxy-1.2-diphenyl-propan；2,3-Diphenyl-propan-1,2-diol；Benzylphenylglycol
• CAS: 155203-78-4
• 化学式: C₁₅H₁₆O₂
• mdl: MFCD25779588
• 分子量: 228.291
• InChiKey: DPSHMGYUJQNALR-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C
• 沸点：
  399.7±37.0 °C(predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (RS)-(+/-)-2,3-diphenyl-1,2-propanediol 在 kieselguhr 作用下， 250.0~300.0 ℃ 、3.33 kPa 条件下， 生成 2,3-diphenylpropanal
  参考文献：
  名称：

  Ramart-Lucas; Salmon-Legagneur, Bulletin de la Societe Chimique de France, 1932, vol. <4> 51, p. 1069,1083

  摘要：

  DOI：
• 作为产物：
  描述：

  5-benzyl-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (RS)-(+/-)-2,3-diphenyl-1,2-propanediol
  参考文献：
  名称：

  Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

  摘要：

  Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents, Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200), Also, the solvent and acyl donor employed influences the outcome, On the basis of the results of Lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained, Fu!! experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given, Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

  DOI：

  10.1039/p19960002051

文献信息

• 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamides as antiviral agents
  申请人：Schnute Edward Mark

  公开号：US20050004161A1

  公开（公告）日：2005-01-06

  The invention provides a compound of formula I: wherein A, B, R 1 , R 2 , R 3 , and R 4 are as defined in the specification. The compounds of the present invention are useful for treating viral infections, in particular a herpesviral infection.

  该发明提供了化合物I的结构，其中A、B、R1、R2、R3和R4如规范中定义。本发明的化合物对治疗病毒感染，特别是单纯疱疹病毒感染，具有实用价值。
• Bach, Thorsten, Liebigs Annalen, 1995, # 6, p. 1045 - 1054
  作者：Bach, Thorsten

  DOI：——

  日期：——
• Regioselective carbohydroxylation of enol ethers by a photocycloaddition-hydrogenation sequence
  作者：Thorsten Bach

  DOI：10.1016/s0040-4039(00)73179-0

  日期：1994.3

  It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Paterno-Buchi reaction the method enables a regioselective access to 1,2-diols 2 starting from olefinic substrates. Optionally, the reduction of 3 can be conducted such that the more hindered tertiary alcohol site in 2 remains silyl-protected.
• On the Catalytic Action of Japanese Acid Earth. XIII. The Catalytic Action on Some Alkyl Aryl Acetaldehydes
  作者：Koshiro Ishimura

  DOI：10.1246/bcsj.16.397

  日期：1941.11
• Lipase catalyzed résolutions of some α,α-disubstituted 1,2-diols in organic solvents; near absolute regio and chiral recognition.
  作者：Robert P. Hof、Richard M. Kellogg

  DOI：10.1016/0957-4166(94)80019-7

  日期：1994.4

  Several racemic 1,2-diols bearing a tertiary benzylic alcohol stereogenic center can be esterified regioselectively by vinyl acetate using lipases and esterases in organic media. With the correct choice of enzyme and if the non-phenyl substituent at the tertiary center is unsaturated, E values of > 250 can be achieved.