(S)-(+)-diisopropyl 1-hydroxy-3-phenylpropylphosphonate | 167933-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (S)-(+)-diisopropyl 1-hydroxy-3-phenylpropylphosphonate
• 英文别名: (S)-diisopropyl (1-hydroxy-3-phenylpropyl)phosphonate；(S)-Diisopropyl 1-hydroxy-3-phenylpropylphosphonate；(1S)-1-di(propan-2-yloxy)phosphoryl-3-phenylpropan-1-ol
• CAS: 167933-61-1
• 化学式: C₁₅H₂₅O₄P
• 分子量: 300.335
• InChiKey: WEMPYJNMOLKRBR-HNNXBMFYSA-N

物化性质

• 沸点：
  414.7±38.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-diisopropyl 1-hydroxy-3-phenylpropylphosphonate 在 偶氮二甲酸二叔丁酯 、 氨 、 三苯基膦 、 (R)-(+)-diisopropyl 1-hydroxy-3-phenylpropylphosphonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.0h， 生成 (R)-(-)-diisopropyl 1-aminooxy-3-phenylpropylphosphonate
  参考文献：
  名称：

  Enzymes in organic chemistry — 5: First and chemo-enzymatic synthesis of α-aminooxyphosphonic acids of high enantiomeric excess

  摘要：

  alpha-Acyloxyphosphonates (+/-)-5a and (+/-)-5b, derived from 3-phenylpropionaldehyde and acetaldehyde. were involved by lipase-catalyzed enantioselective hydrolysis. Three of the four chiral, non-racemic alpha-hydroxyphosphonates obtained had 99% ee. the fourth 91%. They were transformed chemically into alpha-aminooxyphosphonic acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00174-9
• 作为产物：
  描述：

  3-苯丙酰氯 在 (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole 儿萘酚硼烷 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 (S)-(+)-diisopropyl 1-hydroxy-3-phenylpropylphosphonate
  参考文献：
  名称：

  Meier, Chris; Laux, Wolfgang H. G.; Bats, Jan W., Liebigs Annalen, 1995, # 11, p. 1963 - 1980

  摘要：

  DOI：

文献信息

• The Catalytic Asymmetric Abramov Reaction
  作者：Joyram Guin、Qinggang Wang、Manuel van Gemmeren、Benjamin List

  DOI：10.1002/anie.201409411

  日期：2015.1.2

  The first catalytic enantioselective Abramov reaction is described. The process is based on the utilization of a chiral disulfonimide catalyst, which efficiently avoids the difficulties encountered with metal‐based catalysts. Several functionalized α‐hydroxy phosphonates were synthesized in good yields and with excellent enantiomeric ratios of up to >99:1. The process was shown to be scalable and up

  描述了第一催化对映选择性阿布拉莫夫反应。该工艺基于手性二磺酰亚胺催化剂的利用，可有效避免金属基催化剂遇到的困难。合成了几种功能化的α-羟基膦酸酯，收率高，对映体比例高达> 99：1。该方法显示出可扩展性，并且在温和的反应条件下可以使用多达1 g的原料。
• Asymmetric synthesis of chiral, nonracemic dialkyl-α-, β-, and γ-hydroxyalkylphosphonates via a catalyzed enantioselective catecholborane reduction
  作者：Chris Meier、Wolfgang H.G. Laux

  DOI：10.1016/0957-4166(95)00132-9

  日期：1995.5

  A highly enantioselective synthesis of dialkyl alpha-hydroxyphosphonates achieved by a oxazaborolidine catalyzed reduction with catecholborane starting with m-ketophosphonates is described. Both alpha-aryl- and alpha-alkylketophosphonates were reduced using the (S)-enantiomer of the catalyst 4 leading also to the (S)-configuration in the products 2. The reaction gave good chemical yields and excellent enantiomeric excesses (up to >99 % ee).