(S)-diethyl (4-chlorophenyl)(hydroxy)methylphosphonate | 151766-95-9

• 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)-diethyl (4-chlorophenyl)(hydroxy)methylphosphonate
• 英文别名: (S)-diethyl hydroxy(4-chlorophenyl)methylphosphonate；diethyl (4-chlorophenyl)(hydroxy)methylphosphonate；(S)-(4-chlorophenyl)-diethoxyphosphorylmethanol
• CAS: 151766-95-9
• 化学式: C₁₁H₁₆ClO₄P
• 分子量: 278.672
• InChiKey: RIQJHXWKWXDLFM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  4-氯苯甲醛 、 亚磷酸二乙酯 在 potassium phosphate 、 copper diacetate 、 (R,r)-2,2-亚甲基双(4-苯基-2-噁唑啉) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以73%的产率得到(S)-diethyl (4-chlorophenyl)(hydroxy)methylphosphonate
  参考文献：
  名称：

  双（恶唑啉）-铜催化醛的对映选择性氢膦酰化†

  摘要：

  提出了在双（恶唑啉）配体存在下醛的高度对映选择性的铜催化的羰基膦酰化。反应在温和的条件下顺利进行。以高收率和对映选择性（高达98％ee）获得所得的α-羟基膦酸酯。

  DOI：

  10.1039/c4ra03269a

文献信息

• Asymmetric hydrophosphonylation of aldehydes catalyzed by bifunctional chiral Al(III) complexes
  作者：Shaohua Gou、Xin Zhou、Jun Wang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.tet.2008.01.022

  日期：2008.3

  effective enantioselective hydrophosphonylation of aldehydes. A variety of aromatic, heteroaromatic, condensed-ring, α,β-unsaturated, and aliphatic aldehydes were found to be suitable substrates for the reaction, and the desired α-hydroxy phosphonate were obtained in good to excellent yields (up to 99%) with moderate to good enantioselectivities (up to 87% ee) under mild conditions (at 0 °C). A possible

  一种新的手性双官能的Al（Ⅲ）配合物的BINOL衍生物，其中载有叔在BINOL的3,3'-位置-胺，已发展为醛的对映选择性有效hydrophosphonylation。发现各种芳族，杂芳族，稠环，α，β-不饱和和脂族醛是反应的合适底物，并且以良好或优异的收率（高达99％）获得了所需的α-羟基膦酸酯。在温和条件下（0°C）具有中等至良好的对映选择性（高达87％ee）。根据实验结果提出了可能的催化循环。
• Synthesis of an unusual dinuclear chiral iron complex and its application in asymmetric hydrophosphorylation of aldehydes
  作者：Pandi Muthupandi、Govindasamy Sekar

  DOI：10.1039/c2ob25810b

  日期：——

  An unusual dinuclear chiral iron complex has been synthesized and effectively utilized in the asymmetric hydrophosphorylation of aldehydes to synthesize optically active α-hydroxy phosphonates with excellent yield and good enantioselectivity.

  合成了一种不寻常的双核手性铁复合物，并有效地用于醛的非对称氢磷酸化反应，合成了光学活性的α-羟基磷酸酯，产率优秀且对映选择性良好。
• Chiral N,N′-dioxide-Yb(III) complexes catalyzed enantioselective hydrophosphonylation of aldehydes
  作者：Weiliang Chen、Yonghai Hui、Xin Zhou、Jun Jiang、Yunfei Cai、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1016/j.tetlet.2010.05.137

  日期：2010.8

  Chiral N,N'-dioxide-Ytterbium(III) complexes promoted the asymmetric addition of diethyl phosphate to aldehydes, giving the corresponding products with good yields and enantioselectivities. The addition of pyridine favored both reactivity and enantioselectivity. A possible catalytic cycle was proposed to explain the mechanism of the asymmetric hydrophosphonylation of aldehydes. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Hydrophosphonylation of Aldehydes Catalyzed by Tridentate Schiff Base Aluminum(III) Complexes
  作者：Xin Zhou、Xiaohua Liu、Xu Yang、Deju Shang、Junguo Xin、Xiaoming Feng

  DOI：10.1002/anie.200704116

  日期：2008.1