ethyl 2-(4-chlorophenyl)-2-(4-methylphenylsulfonamido)acetate | 1108736-40-8

• 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: ethyl 2-(4-chlorophenyl)-2-(4-methylphenylsulfonamido)acetate
• 英文别名: ethyl (+/-)-(4-chlorophenyl)(tosylamino)acetate；N-tosyl-2-(4-chlorophenyl)glycine ethyl ester；Ethyl 2-(4-chlorophenyl)-2-[(4-methylphenyl)sulfonylamino]acetate
• CAS: 1108736-40-8；1384465-80-8
• 化学式: C₁₇H₁₈ClNO₄S
• 分子量: 367.853
• InChiKey: YJKBHTKATUGIMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  ethyl 2-(4-chlorophenyl)-2-(4-methylphenylsulfonamido)acetate 、 (2-溴乙基)二苯基锍三氟甲烷磺酸盐 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到ethyl (+/-)-2-(4-chlorophenyl)-1-tosylazetidine-2-carboxylate
  参考文献：
  名称：

  （2-溴乙基）三氟甲磺酸late高效合成氮杂环丁烷

  摘要：

  摘要 通过使用市售的（2-溴乙基）三氟甲磺酸in，以简单且温和的步骤将容易获得的芳基甘氨酸衍生物环化为氮杂环丁烷。高产率反应具有相对广泛的范围，并扩展到氧杂环丁烷的合成。 通过使用市售的（2-溴乙基）三氟甲磺酸in，以简单且温和的步骤将容易获得的芳基甘氨酸衍生物环化为氮杂环丁烷。高产率反应具有相对广泛的范围，并扩展到氧杂环丁烷的合成。

  DOI：

  10.1055/s-0031-1290951
• 作为产物：
  描述：

  对甲苯磺酰胺 在 二氟化氢钾 、 [Rh(OH)(cod)]2 、 三氟化硼乙醚 、 (+)-N-苄基-(3R,4R)-双(二苯基膦)吡咯烷 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 48.0h， 生成 ethyl 2-(4-chlorophenyl)-2-(4-methylphenylsulfonamido)acetate
  参考文献：
  名称：

  Ethyl 2,2-bis(4-methylphenylsulfonamido)acetate to aromatic α-amino acids: stable substrates for catalytic arylation reactions

  摘要：

  This paper reports the development of a novel methodology for the catalytic synthesis of aromatic alpha-amino acids, which involves the addition of aryl-organoboron reagents to alpha,alpha-ditosylamino esters derived from ethyl glyoxylate, using transition metal catalysts, like Rh and Pd. A library of alpha-amino esters (12 with Pd and 8 with Rh), was synthesized with moderate to excellent yields. A highest enantioselectivity of 30% ee was obtained using Hayashi's ligand. This method was applied to the synthesis of phenylglycine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.053

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。
• Palladium(II)-Catalyzed One-Pot Enantioselective Synthesis of Arylglycine Derivatives from Ethyl Glyoxylate,p-Toluenesulfonyl Isocyanate and Arylboronic Acids
  作者：Huixiong Dai、Miao Yang、Xiyan Lu

  DOI：10.1002/adsc.200700362

  日期：2008.1.25

  A palladium(II)-catalyzed, one-pot enantioselective synthesis of arylglycine derivatives from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids giving moderate to good yields and enantioselectivity has been developed. This reaction provides a convenient and efficient method for the synthesis of arylglycines.

  已经开发了钯（II）催化的由乙醛酸乙酯，对甲苯磺酰基异氰酸酯和芳基硼酸一锅对映选择性合成芳基甘氨酸衍生物，产生中等至良好的产率和对映选择性。该反应为合成芳基甘氨酸提供了方便而有效的方法。
• Ethyl 2,2-bis(4-methylphenylsulfonamido)acetate to aromatic α-amino acids: stable substrates for catalytic arylation reactions
  作者：Carolina S. Marques、Anthony J. Burke

  DOI：10.1016/j.tet.2013.09.053

  日期：2013.11

  This paper reports the development of a novel methodology for the catalytic synthesis of aromatic alpha-amino acids, which involves the addition of aryl-organoboron reagents to alpha,alpha-ditosylamino esters derived from ethyl glyoxylate, using transition metal catalysts, like Rh and Pd. A library of alpha-amino esters (12 with Pd and 8 with Rh), was synthesized with moderate to excellent yields. A highest enantioselectivity of 30% ee was obtained using Hayashi's ligand. This method was applied to the synthesis of phenylglycine. (C) 2013 Elsevier Ltd. All rights reserved.
• An Efficient Synthesis of Azetidines with (2-Bromoethyl)sulfonium Triflate
  作者：Eoghan McGarrigle、Varinder Aggarwal、Sven Fritz、Juan Moya、Matthew Unthank

  DOI：10.1055/s-0031-1290951

  日期：2012.5

  commercially available (2-bromoethyl)sulfonium triflate in a simple and mild procedure. The high-yielding reaction has a relatively broad scope and was extended to the synthesis of an oxetane. Easily accessible arylglycine derivatives were cyclized to azetidines by using commercially available (2-bromoethyl)sulfonium triflate in a simple and mild procedure. The high-yielding reaction has a relatively broad scope

  摘要 通过使用市售的（2-溴乙基）三氟甲磺酸in，以简单且温和的步骤将容易获得的芳基甘氨酸衍生物环化为氮杂环丁烷。高产率反应具有相对广泛的范围，并扩展到氧杂环丁烷的合成。 通过使用市售的（2-溴乙基）三氟甲磺酸in，以简单且温和的步骤将容易获得的芳基甘氨酸衍生物环化为氮杂环丁烷。高产率反应具有相对广泛的范围，并扩展到氧杂环丁烷的合成。