s(-)-dimethyl o-chloro-α-hydroxybenzylphosphonate | 97939-09-8

• 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: s(-)-dimethyl o-chloro-α-hydroxybenzylphosphonate
• 英文别名: (S)-Dimethyl (2-chlorophenyl)hydroxymethylphosphonate；(S)-dimethyl hydroxy(2-chlorophenyl)methylphosphonate；dimethyl [hydroxy(2-chlorophenyl)methyl]phosphonate；(S)-(2-chlorophenyl)-dimethoxyphosphorylmethanol
• CAS: 97939-09-8
• 化学式: C₉H₁₂ClO₄P
• 分子量: 250.619
• InChiKey: XLXMBCJIFSDGAC-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  [(S)-(2-Amino-phenyl)-hydroxy-methyl]-phosphonic acid dimethyl ester 在 盐酸 、 copper(l) chloride 、 sodium nitrite 作用下， 生成 s(-)-dimethyl o-chloro-α-hydroxybenzylphosphonate
  参考文献：
  名称：

  α-羟基膦酸酯的绝对构型

  摘要：

  一系列手性α-羟基膦酸酯和磷酸的绝对构型和CD光谱已确定。通过奎宁催化的亚磷酸酯与醛的1,2-加成反应制备羟基膦酸酯。

  DOI：

  10.1016/s0040-4039(00)61920-2

文献信息

• Highly Enantioselective Hydrophosphonylation of Aldehydes: Base-Enhanced Aluminum-salalen Catalysis
  作者：Keitaro Suyama、Yoshifumi Sakai、Kazuhiro Matsumoto、Bunnai Saito、Tsutomu Katsuki

  DOI：10.1002/anie.200905158

  日期：2010.1.18

  The dimethyl phosphonate hydrophosphonylation of conjugated‐ and non‐conjugated aldehydes into their corresponding α‐hydroxy phosphonates was achieved using chiral aluminum–salalen complex 1 (see scheme).

  使用手性铝-salalen配合物1（参见方案）可将共轭醛和非共轭醛的二甲基膦酸氢膦酰化为相应的α-羟基膦酸酯。
• Enantioselective synthesis of α-hydroxy phosphonates via oxidation with (camphorsulfonyl)oxaziridines
  作者：Diana M. Pogatchnik、David F. Wiemer

  DOI：10.1016/s0040-4039(97)00705-3

  日期：1997.5

  Reaction of phosphonate anions with enantiomerically pure (camphorsulfonyl)oxaziridines results in formation of nonracemic alpha-hydroxy phosphonates. This enantioselective hydroxylation methodology provides convenient access to optically active alpha-hydroxy phosphonates and their corresponding phosphonic acids. (C) 1997 Elsevier Science Ltd.
• Synthesis of an Optically ActiveC1-Symmetric Al(salalen) Complex and Its Application to the Catalytic Hydrophosphonylation of Aldehydes
  作者：Bunnai Saito、Tsutomu Katsuki

  DOI：10.1002/anie.200501008

  日期：2005.7.18
• 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：——
• Synthesis, structure, and catalytic activity of titanium complexes with chiral biaryl Schiff-base ligands
  作者：Liang Chen、Ning Zhao、Qiuwen Wang、Guohua Hou、Haibin Song、Guofu Zi

  DOI：10.1016/j.ica.2013.04.008

  日期：2013.6

  A series of chiral organo-titanium complexes have been prepared from the reaction between Ti((OPr)-Pr-i)(4) and chiral biaryl Schiff-base ligands 1H(2)-12H. The steric demand of the ligand plays an important role in the formation of the titanium complexes. For example, treatment of ligand 1H(2) with 1 equiv of Ti((OPr)-Pr-i)(4) in toluene at room temperature gives, after recrystallization from a toluene solution, the chiral bis-ligated titanium complex (L1)(2)Ti (14). While under similar reaction conditions, the more bulky ligands 2H(2), 4H(2), and 6H(2) form the mono-ligated titanium complexes (L2)Ti((OPr)-Pr-i)(2) (15), (L4)Ti((OPr)-Pr-i)(2)(19), and (L6)Ti((OPr)-Pr-i)(2) (22), respectively, in good yields. The mono-ligated titanium alkoxides can be converted to bis-ligated complex via ligand redistribution reaction. For one instance, treatment of mono-ligated complex (L2)Ti((OPr)-Pr-i)(2) (15) in benzene at 60 degrees C results in the isolation of the bis-ligated complex (L2)(2)Ti (16) in 92% yield. All titanium complexes have been characterized by various spectroscopic techniques and elemental analyses. The solid-state structures of complexes 14-21, 23, 24 and 29 have further been confirmed by X-ray diffraction analyses. The titanium complexes are active catalysts for the asymmetric hydrophosphonylation of aromatic aldehydes with moderate enantioselectivities. (C) 2013 Elsevier B.V. All rights reserved.