(S)-benzyl 2-((4-methylphenyl)sulfonamido)-2-phenylacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-benzyl 2-((4-methylphenyl)sulfonamido)-2-phenylacetate
• 英文别名: benzyl (2S)-2-[(4-methylphenyl)sulfonylamino]-2-phenylacetate
• 化学式: C₂₂H₂₁NO₄S
• 分子量: 395.479
• InChiKey: ISISGLWHAAGRRN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-((4-methylphenyl)sulfonamido)-2-phenylacetate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(2S)-2-phenyl-2-(tosylamino)acetic acid
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

  摘要：

  An efficient Pd(OAc)(2)-catalyzed asymmetric hydrogenation of alpha-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)(2), a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)(2) which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral alpha-arylglycine fragments are widely found in many chiral products and bioactive molecules.

  DOI：

  10.1021/acs.orglett.9b03452
• 作为产物：
  描述：

  benzyl oxo(phenyl)acetate 在 (R,R)-QuinoxP 、 氢气 、 palladium diacetate 、 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 24.0h， 生成 (S)-benzyl 2-((4-methylphenyl)sulfonamido)-2-phenylacetate
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

  摘要：

  An efficient Pd(OAc)(2)-catalyzed asymmetric hydrogenation of alpha-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)(2), a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)(2) which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral alpha-arylglycine fragments are widely found in many chiral products and bioactive molecules.

  DOI：

  10.1021/acs.orglett.9b03452

文献信息

• Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines
  作者：Tamara Beisel、Andreas M. Diehl、Georg Manolikakes

  DOI：10.1021/acs.orglett.6b02045

  日期：2016.8.19

  A general Pd-catalyzed, enantioselective three-component synthesis of α-arylglycines starting from sulfonamides, glyoxylic acid derivatives, and boronic acids was developed. This operationally straightforward procedure enables the preparation of a wide variety of α-arylglycines in high yields and excellent levels of enantioselectivity from a simple set of readily available starting materials. Incorporation

  从磺酰胺，乙醛酸衍生物和硼酸开始，开发了一种一般的Pd催化的α-芳基甘氨酸的对映选择性三组分合成方法。该操作简单的方法能够从一组简单易得的起始原料中以高收率和优异的对映选择性制备多种α-芳基甘氨酸。掺入Pbf-酰胺可无外消旋地接近N-未保护的α-芳基甘氨酸。
• Pd(OAc)₂-Catalyzed Asymmetric Hydrogenation of α-Iminoesters
  作者：Jianzhong Chen、Feilong Li、Fang Wang、Yawen Hu、Zhenfeng Zhang、Min Zhao、Wanbin Zhang

  DOI：10.1021/acs.orglett.9b03452

  日期：2019.11.15

  An efficient Pd(OAc)(2)-catalyzed asymmetric hydrogenation of alpha-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)(2), a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)(2) which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral alpha-arylglycine fragments are widely found in many chiral products and bioactive molecules.