(1R*,R*_P)-ethyl 1-{[(4-methylphenyl)sulfonyl]-amino}-2-phenylethyl phosphinate

• 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: (1R*,R*_P)-ethyl 1-{[(4-methylphenyl)sulfonyl]-amino}-2-phenylethyl phosphinate
• 化学式: C₁₇H₂₂NO₄PS
• 分子量: 367.4
• InChiKey: DJAGUAKTXSGRQR-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R*,R*_P)-ethyl 1-{[(4-methylphenyl)sulfonyl]-amino}-2-phenylethyl phosphinate 、 N-(2-furylmethylene)aniline 在 ytterbium trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 ethyl anilino(2-furyl)methyl((R*)-1-{[(4-methylphenyl)sulfonyl]amino}-2-phenylethyl)phosphinate 、 ethyl anilino(2-furyl)methyl((R*)-1-{[(4-methylphenyl)sulfonyl]amino}-2-phenylethyl)phosphinate
  参考文献：
  名称：

  Diastereoselective addition of α-substituted α-amino-H-phosphinates to imines using Yb(OTf)3 as an efficient Lewis acid catalyst

  摘要：

  Diastereoselective addition of alpha-substituted alpha-amino-H-phosphinates to imines is described. Among Lewis acids, Yb(OTf)(3) was found to be the best catalyst. alpha,alpha'-Diaminophosphinic derivatives were obtained with de's ranging from 10 to 95% in the presence of Yb(OTf)(3) as an efficient Lewis acid catalyst. The reaction proceeded with retention of configuration at the phosphorus atom. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.118

文献信息

• Nickel-catalyzed C–P cross-coupling reactions of aryl iodides with H-phosphinates
  作者：Atsushi Kinbara、Momoko Ito、Tohru Abe、Takehiro Yamagishi

  DOI：10.1016/j.tet.2015.07.073

  日期：2015.10

  Synthesis of aryl phosphinates was achieved through cross-coupling reactions of aryl iodides with H-phosphinates catalyzed by nickel under mild conditions. The method was applicable to various aryl iodides and H-phosphinates having defined stereochemistry at the phosphorus atom.

  芳基次膦酸酯的合成是通过芳基碘化物与镍催化的H-次膦酸酯在温和条件下的交叉偶联反应而实现的。该方法适用于在磷原子上具有确定的立体化学的各种芳基碘化物和H-次膦酸酯。
• Asymmetric synthesis of optically active α-substituted α-amino-H-phosphinates through resolution of 1,1-diethoxyethyl(aminomethyl)phosphinates
  作者：Terumitsu Haruki、Takehiro Yamagishi、Tsutomu Yokomatsu

  DOI：10.1016/j.tetasy.2007.11.021

  日期：2007.12

  Both enantiomers of 1,1-diethoxyethyl(aminomethyl)phosphinates were prepared through chromatographic separation of a diastereomeric mixture derived from (S)-phenylethylamine and 1,1-diethoxyethyl-H-phosphinate. The individual enantiomer was transformed into α-substituted α-amino-H-phosphinate with high enantiomeric purity by a highly diastereoselective alkylation at the α-carbon on the basis of our

  1,1-二乙氧基乙基的两种对映体（氨基甲基）次膦酸盐是通过从（衍生的非对映体混合物的色谱分离制备的小号）苯乙胺和1,1- diethoxyethyl- ħ -phosphinate。的单个对映体转化为α取代的α氨基ħ通过在我们的先前开发的方法的基础上的α碳上的高度非对映烷基化-phosphinate具有高对映体纯度。
• Diastereoselective Synthesis of α,β′-Disubstituted Aminomethyl(2-carboxyethyl)phosphinates as Phosphinyl Dipeptide Isosteres
  作者：Takehiro Yamagishi、Hiroyuki Ichikawa、Terumitsu Haruki、Tsutomu Yokomatsu

  DOI：10.1021/ol801743d

  日期：2008.10.2

  A new and efficient method has been developed for the diastereoselective synthesis of unnatural dipeptide analogues containing the metabolically stable phosphinic moiety, NH 2XaaPsi[P(O)OHCH 2]XaaOH, which mimics the transition state of tetrahedral geometry of a scissile peptide bond in hydrolysis by protease. The method is based upon stereospecific Michael addition of stereodefined alpha-aminoalkyl-

  已开发出一种新的有效方法，用于非对映二聚体合成非天然二肽类似物，该类似物含有代谢稳定的次膦酸酯部分NH 2XaaPsi [P（O）OHCH 2] XaaOH，其模拟了水解中易裂肽键的四面体几何结构的过渡态通过蛋白酶。该方法基于将立体定义的α-氨基烷基-H-次膦酸酯的立体特异性迈克尔加成到丙烯酸酯上，以及随后在所得迈克尔加合物的β'-位置上的非对映选择性烷基化。
• Diastereoselective Synthesis of Novel α-Amino-α′-hydroxyphosphinates by Hydrophosphinylation of α-Amino-<i>H</i>-phosphinates to Aldehydes
  作者：Babak Kaboudin、Tsutomu Yokomatsu、Terumitsu Haruki、Takehiro Yamagishi

  DOI：10.1055/s-2007-990785

  日期：2007.10

  Synthesis of α-amino-α′-hydroxyphosphinates has been achieved through hydrophosphinylation of α-amino-H-phosphinates to aldehydes with highly retentive phosphorus chirality. Treatment of α-substituted α-amino-H-phosphinates with aldehydes in the presence of magnesium oxide without solvent gave α-amino-α′-hydroxyphosphinates. The reaction proceeded with 80-94 % retention of configuration at the phosphorus atom.

  δ-氨基-δ′-羟基膦酸盐的合成是通过将δ-氨基-H-膦酸盐与具有高度保留磷手性的醛进行氢膦化来实现的。在无溶剂的情况下，在氧化镁存在下将δ-取代的δ-氨基-H-膦酸与醛处理，可得到δ-氨基-δ′-羟基膦酸。反应进行时，磷原子上的构型保留了 80-94%。
• Diastereoselective alkylation of iminomethylenephosphinates possessing an asymmetric center at the phosphorus atom
  作者：Takehiro Yamagishi、Terumitsu Haruki、Tsutomu Yokomatsu

  DOI：10.1016/j.tet.2006.07.029

  日期：2006.9

  Diastereoselective synthesis of alpha-aminophosphinates was achieved by alkylation of imines with a 1,1-diethoxyethylphosphinyl group. These products were readily converted into alpha-amino-H-phosphinates. (c) 2006 Elsevier Ltd. All rights reserved.