dimethyl [hydroxy(4-fluorophenyl)methyl]phosphonate

• 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: dimethyl [hydroxy(4-fluorophenyl)methyl]phosphonate
• 英文别名: (R)-dimethoxyphosphoryl-(4-fluorophenyl)methanol
• 化学式: C₉H₁₂FO₄P
• 分子量: 234.164
• InChiKey: KBGSFLPVYJDWMS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 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：
  5

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 、 亚磷酸二甲酯 在 C₃₈H₄₈N₄P⁽¹⁺⁾*Cl^(1-) 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以97%的产率得到dimethyl [hydroxy(4-fluorophenyl)methyl]phosphonate
  参考文献：
  名称：

  [5.5]-P-螺环手性三氨基亚氨基正膦催化醛和炔酮的不对称氢膦酰化

  摘要：

  描述了由 [5.5]-P-螺环手性三氨基亚氨基正膦作为碱催化剂介导的醛和炔酮的高效和对映选择性氢膦酰化的开发。天...

  DOI：

  10.1246/bcsj.20170040

文献信息

• Enantioselective Hydrophosphonylation of Aldehydes Using an Aluminum Binaphthyl Schiff Base Complex as a Catalyst
  作者：Katsuji Ito、Hironori Tsutsumi、Masayuki Setoyama、Bunnai Saito、Tsutomu Katsuki

  DOI：10.1055/s-2007-984528

  日期：2007.7

  An aluminum binaphthyl Schiff base complex was found to be an efficient catalyst for enantioselective hydrophosphonylation of aldehydes. High enantioselectivities were obtained in reactions of both aromatic and aliphatic aldehydes (up to 84% and 86% ee, respectively).

  研究发现，一种铝二萘基希夫碱复合物是对映体选择性氢膦酰化醛的高效催化剂。在芳香醛和脂肪醛的反应中都获得了较高的对映选择性（ee值分别高达 84% 和 86%）。
• New homochiral cyclic diol ligands for titanium alkoxide catalyzed phosphonylation of aldehydes
  作者：Michael D. Groaning、Bradley J. Rowe、Christopher D. Spilling

  DOI：10.1016/s0040-4039(98)01139-3

  日期：1998.7

  An investigation of the structural effects of chiral diol ligands on the enantioselectivity of phosphorylation was performed. Cyclic diols, and cyclohexanediol in particular, were identified as effective ligands for titanium alkoxide catalyzed asymmetric phosphorylation. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.
• [5.5]-<i>P</i>-Spirocyclic Chiral Triaminoiminophosphorane-Catalyzed Asymmetric Hydrophosphonylation of Aldehydes and Ynones
  作者：Daisuke Uraguchi、Takaki Ito、Yuto Kimura、Yumiko Nobori、Makoto Sato、Takashi Ooi

  DOI：10.1246/bcsj.20170040

  日期：2017.5.15

  Development of highly efficient and enantioselective hydrophosphonylations of aldehydes and ynones mediated by [5.5]-P-spirocyclic chiral triaminoiminophosphoranes as base catalysts is described. T...

  描述了由 [5.5]-P-螺环手性三氨基亚氨基正膦作为碱催化剂介导的醛和炔酮的高效和对映选择性氢膦酰化的开发。天...