ethyl 2-(4-methylphenylsulfonamido)-2-(naphthalen-1-yl)acetate

• 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-methylphenylsulfonamido)-2-(naphthalen-1-yl)acetate
• 英文别名: Ethyl 2-[(4-methylphenyl)sulfonylamino]-2-naphthalen-1-ylacetate
• 化学式: C₂₁H₂₁NO₄S
• 分子量: 383.468
• InChiKey: AEVXHJMDGQOMML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 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-methylphenylsulfonamido)-2-(naphthalen-1-yl)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(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.