ethyl 2-(4-methylphenylsulfonamido)-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: ethyl 2-(4-methylphenylsulfonamido)-2-phenylacetate
• 英文别名: N-tosyl(phenylglycine) ethyl ester；N-tosyl DL-phenylglycine ethyl ester；Ethyl 2-((4-methylphenyl)sulfonamido)-2-phenylacetate；ethyl 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetate
• 化学式: C₁₇H₁₉NO₄S
• 分子量: 333.408
• InChiKey: VJXHDZRODBOXNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 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-methylphenylsulfonamido)-2-phenylacetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以90%的产率得到2-氨基-2-苯基乙酸
  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
• 作为产物：
  描述：

  2-重氮基-2-苯基乙酸乙酯 在 potassium carbonate 、 苯硫酚 作用下， 以 氯仿 、 乙腈 为溶剂， 生成 ethyl 2-(4-methylphenylsulfonamido)-2-phenylacetate
  参考文献：
  名称：

  重氮羰基化合物的胺化：无金属条件下的NH插入

  摘要：

  据报道，无过渡金属的α-重氮羰基化合物的分子间NH插入。在所检查的一系列氮源中，发现二苯磺酰亚胺是产率和反应时间的选择。初步的机械实验表明，涉及质子化和亲核取代序列的途径是优选的。

  DOI：

  10.1021/acs.joc.6b00233

文献信息

• Ruthenium-Catalyzed One-Pot Carbenoid N−H Insertion Reactions and Diastereoselective Synthesis of Prolines
  作者：Qing-Hai Deng、Hai-Wei Xu、Angella Wing-Hoi Yuen、Zhen-Jiang Xu、Chi-Ming Che

  DOI：10.1021/ol800087p

  日期：2008.4.1

  3-hydroxyprolines and various other amino esters are conveniently prepared by [RuCl2(p-cymene)]2-catalyzed one-pot intramolecular and intermolecular carbenoid N-H insertion reactions, respectively, and the prolines are formed with high diastereoselectivities. The catalytic reactions are tolerant toward air/moisture, and the product yields are insensitive to the organic solvents used.

  芳基和脂族取代的3-羟基脯氨酸和各种其他氨基酸酯分别通过[RuCl2（p-cymene）] 2-催化的一锅分子内和分子间类胡萝卜素NH插入反应可方便地制备，且脯氨酸具有高非对映选择性。催化反应对空气/水分具有耐受性，并且产物收率对所用有机溶剂不敏感。
• 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。
• 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。
• Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
  作者：Fabio Juliá、Jiyao Yan、Fritz Paulus、Tobias Ritter

  DOI：10.1021/jacs.1c06632

  日期：2021.8.25

  The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry

  乙烯基亲电子试剂在合成中的使用受到了阻碍，因为无法获得实用且具有适当反应性的合适试剂。在这项工作中，我们引入了乙烯基铪盐作为有效的乙烯基化试剂。这种实验室稳定的结晶试剂可以很容易地在大气压下一步由乙烯气体制备，并且广泛用于（杂）环的环化化学、杂环化合物的 N-乙烯基化和钯催化的交叉偶联反应。噻蒽核心的结构特征实现了独特的合成和反应特性，这是其他乙烯基锍衍生物前所未有的。
• Rhodium-catalyzed addition of arylstannanes to carbon–heteroatom double bond
  作者：Shuichi Oi、Mitsutoshi Moro、Hiroe Fukuhara、Takanori Kawanishi、Yoshio Inoue

  DOI：10.1016/s0040-4020(03)00586-6

  日期：2003.6

  The addition of arylstannanes to the carbon–heteroatom double bond in the presence of a catalytic amount of a cationic rhodium complex ([Rh(cod)(MeCN)2]BF4) was examined. The reactions of aldehydes, α-dicarbonyl compounds, and N-substituted aldimines with the arylstannanes gave corresponding alcohols, α-hydroxy carbonyl compounds, and amines, respectively. An arylrhodium complex generated by the transmetalation

  研究了在催化量的阳离子铑配合物（[Rh（cod）（MeCN）2 ] BF 4）存在下，向碳-杂原子双键中添加了芳基锡烷。醛，α-二羰基化合物和N-取代的亚胺与芳基锡烷的反应分别得到相应的醇，α-羟基羰基化合物和胺。通过芳基锡烷的重金属化反应生成的芳基铑络合物可能是活性催化物质。