(R)-Diisopropyl (4-chlorophenyl)hydroxymethylphosphonate

• 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: (R)-Diisopropyl (4-chlorophenyl)hydroxymethylphosphonate
• 英文别名: (R)-(4-chlorophenyl)-di(propan-2-yloxy)phosphorylmethanol
• 化学式: C₁₃H₂₀ClO₄P
• 分子量: 306.726
• InChiKey: HHXAPODRXNWZLQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三异丙基亚磷酸酯 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 (R)-Diisopropyl (4-chlorophenyl)hydroxymethylphosphonate
  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

• Enantioselective synthesis of diisopropyl α-, β-, and γ-hydroxyarylalkylphosphonates from ketophosphonates: A study on the effect of the phosphonyl group
  作者：Chris Meier、Wolfgang H.G. Laux

  DOI：10.1016/0040-4020(95)00855-1

  日期：1996.1

  conditions to an enantioselective synthesis of diisopropyl α-, β- and γ-hydroxyphosphonates 4–6 by 1.3.2-oxazaborolidine catalysis using catecholborane 7 or BH3·Me2S 8 is described. The comparison to acetophenone reductions gave information's on the effect of the phosphonyl group during the reduction of ketophosphonate. So very efficient syntheses to chiral dialkyl α-, β- and γ-hydroxyphosphonates were

  描述了使用儿茶酚硼烷7或BH 3 ·Me 2 S 8通过1.3.2-恶唑硼烷催化的不同还原条件与对映体选择性合成α-，β-和γ-羟基磷酸二异丙酯4-6的比较。与苯乙酮还原的比较给出了在酮膦酸酯还原过程中膦酰基的作用的信息。因此，精心设计了非常高效的手性二烷基α-，β-和γ-羟基膦酸酯的合成方法。
• Imidazolium ion tethered TsDPENs as efficient ligands for Iridium catalyzed asymmetric transfer hydrogenation of α-keto phosphonates in water
  作者：Mengxia Sun、Joann Campbell、Guowei Kang、Huigang Wang、Bukuo Ni

  DOI：10.1016/j.jorganchem.2016.03.010

  日期：2016.5

  Iridium-catalyzed asymmetric transfer hydrogenation (ATH) of α-ketophosphonates in water. The reaction provided the desired product α-hydroxyphosphonates in moderate to good yields (44–78%) and good to excellent enantioselectivities (up to >99% ee) under mild reaction conditions without adding any surfactants. The enantiomeric excess was determined by 13P NMR by using (−)-cinchonidine as chiral solvating agent

  首次，通过使用咪唑鎓离子束缚的TsDPENs作为铱在水中α-酮膦酸酯的铱催化的不对称转移氢化（ATH）的有效配体，开发了一种有效的方法。该反应在不添加任何表面活性剂的条件下，在温和的反应条件下，以中等至良好的收率（44-78％）和良好至出色的对映选择性（高达> 99％ee）提供了所需的产物α-羟基膦酸酯。通过使用（-）-金可尼定作为手性溶剂化剂，通过13 P NMR测定对映体过量，这是一种比手性HPLC更方便的方法。
• 1,1′-Dibenzyl-bis-(triazolyl)diphenylphosphine dioxide: a new efficient organocatalyst for silicon tetrachloride-mediated enantioselective Abramov-type phosphonylation of aldehydes with trialkyl phosphites
  作者：Nicolas Sevrain、Jean-Noël Volle、Jean-Luc Pirat、Tahar Ayad、David Virieux

  DOI：10.1039/c7ra10919a

  日期：——

  Asymmetric phosphonylation of aldehydes with trialkyl phosphites using a combination of SiCl4 and a novel 1,1′-dibenzyl-bis-(triazolyl)diphenylphosphine dioxide organocatalyst has been developed. This protocol provides the corresponding α-hydroxyphosphonates with a broad range of functional groups and substitution patterns in excellent yields and good selectivities.

  已经开发了使用SiCl 4和新型的1,1'-二苄基-双-（三唑基）二苯基膦二氧化膦有机催化剂组合的醛与亚磷酸三烷基酯的不对称膦酰化反应。该方案以优异的产率和良好的选择性为相应的α-羟基膦酸酯提供了广泛的官能团和取代方式。
• 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).
• Meier, Chris; Laux, Wolfgang H. G.; Bats, Jan W., Liebigs Annalen, 1995, # 11, p. 1963 - 1980
  作者：Meier, Chris、Laux, Wolfgang H. G.、Bats, Jan W.

  DOI：——

  日期：——