(S)-dimethyl hydroxy(4-nitrophenyl)methylphosphonate

• 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 hydroxy(4-nitrophenyl)methylphosphonate
• 英文别名: dimethyl (S)-hydroxy(4-nitrophenyl)methylphosphonate；dimethyl (S)-hydroxy(p-nitrophenyl)methylphosphonate；dimethyl [hydroxy(4-nitrophenyl)methyl]phosphonate；(S)-dimethoxyphosphoryl-(4-nitrophenyl)methanol
• 化学式: C₉H₁₂NO₆P
• 分子量: 261.171
• InChiKey: WKULVHLZPACKQK-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 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：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dimethyl (4-nitrobenzyl)phosphonate 在 (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-dimethyl hydroxy(4-nitrophenyl)methylphosphonate 、 dimethyl (R)-hydroxy(4-nitrophenyl)methylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of α-hydroxy phosphonates via oxidation with (camphorsulfonyl)oxaziridines

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)00705-3

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。
• Synthesis of an Optically Active Al(salalen) Complex and Its Application to Catalytic Hydrophosphonylation of Aldehydes and Aldimines
  作者：Bunnai Saito、Hiromichi Egami、Tsutomu Katsuki

  DOI：10.1021/ja0651005

  日期：2007.2.1

  serve as an efficient catalyst for hydrophosphonylation of aldehydes and aldimines, giving the corresponding alpha-hydroxy and alpha-amino phosphonates with high enantioselectivity, respectively. The scope of the hydrophosphonylation was wide, and both aliphatic and aromatic aldehydes and aldimines were successfully used as substrates for the reaction. The potent catalysis of the complex is attributed to

  以模块化合成方式新合成了光学活性铝（salalen）配合物2，发现它可作为醛和醛亚胺氢膦酰化的有效催化剂，分别得到相应的具有高对映选择性的α-羟基和α-氨基膦酸酯. 氢膦酰化的范围很广，脂肪族和芳香族醛和醛亚胺都成功地用作反应的底物。该复合物的强大催化作用归因于其独特的结构：它采用扭曲的三角双锥体构型，这使得 salalen 配体呈顺式-β 样结构，其中手性氨基位于靠近金属中心的位置。
• Organocatalytic enantioselective hydrophosphonylation of aldehydes
  作者：Juan V. Alegre-Requena、Eugenia Marqués-López、Pablo J. Sanz Miguel、Raquel P. Herrera

  DOI：10.1039/c3ob42403k

  日期：——

  our results concerning the first squaramide-catalysed hydrophosphonylation of aldehydes. In all cases, the reactions proceeded smoothly and cleanly under mild reaction conditions rendering final α-hydroxy phosphonates in very good yields and high enantioselectivities. It is one of the few organocatalytic examples of this reaction using aldehydes. It is the first time that diphenylphosphite (1e) has

  我们报告有关醛的第一个方胺催化的氢膦酰化反应的结果。在所有情况下，反应均在温和的反应条件下平稳而干净地进行，从而以非常好的收率和高对映选择性产生最终的α-羟基膦酸酯。它是使用醛的该反应的少数有机催化实例之一。与先前公开的方法中使用的亚磷酸二烷基酯相反，这是首次将亚磷酸二苯基酯（1e）成功用于醛的手性Pudovik反应中，从而扩大了这种不对称方法的通用性。
• Process for preparing asymmetric compound by using metal complex
  申请人：Nagase & Company, Ltd.

  公开号：US05847186A1

  公开（公告）日：1998-12-08

  A process for producing an asymmetric compound using a metal complex containing no rare earth metal element is disclosed. The process affords an optically active compound having high optical purity. Optically active binaphthol having the chemical formula ##STR1## and lithium aluminum hydride are reacted, or the optically active binaphthol, a dialkyl aluminum hydride, and a base containing an alkali metal (or a base containing alkaline earth metal) are reacted to prepare a metal complex comprising optically active binaphthol, aluminum, and alkali metal (or alkaline earth metal). This metal complex can be used as a catalyst to perform an asymmetric Michael reaction, an asymmetric phosphonylation reaction, or the like, to obtain, in a high yield, an asymmetric compound having high optical purity.

  揭示了一种使用不含稀土金属元素的金属配合物制备不对称化合物的方法。该方法可以得到具有高光学纯度的光学活性化合物。将具有化学式##STR1##的光学活性二联萘酚和锂铝氢化物反应，或将光学活性二联萘酚、二烷基铝氢化物和含有碱金属（或含有碱土金属）的碱反应以制备包含光学活性二联萘酚、铝和碱金属（或碱土金属）的金属配合物。该金属配合物可用作催化剂进行不对称Michael反应、不对称磷酰化反应等，以高产率获得高光学纯度的不对称化合物。
• Process for the preparation of an asymmetric compound using a metal
  申请人：Nagase and Co., Ltd.

  公开号：US06090969A1

  公开（公告）日：2000-07-18

  A process for producing an asymmetric compound using a metal complex containing no rare earth metal element is disclosed. The process affords an optically active compound having high optical purity. Optically active binaphthol having the chemical formula and lithium aluminum hydride are reacted, or the optically active binaphthol, a dialkyl aluminum hydride, and a base containing an alkali metal (or a base containing alkaline earth metal) are reacted to prepare a metal complex comprising optically active binaphthol, aluminum, and alkali metal (or alkaline earth metal). This metal complex can be used as a catalyst to perform an asymmetric Michael reaction, an asymmetric phosphonylation reaction, or the like, to obtain, in a high yield, an asymmetric compound having high optical purity.

  本发明揭示了一种使用不含稀土金属元素的金属配合物制备不对称化合物的方法。该方法可得到具有高光学纯度的光学活性化合物。可将具有化学式的光学活性双萘酚和锂铝氢化物反应，或将光学活性双萘酚、二烷基铝氢化物和含有碱金属（或含有碱土金属）的碱反应以制备包含光学活性双萘酚、铝和碱金属（或碱土金属）的金属配合物。该金属配合物可用作催化剂进行不对称Michael反应、不对称磷酰化反应等，以高产率获得高光学纯度的不对称化合物。