benzenesulfonyl-(4-methoxy-phenyl)-acetic acid ethyl ester | 190672-11-8

• 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: benzenesulfonyl-(4-methoxy-phenyl)-acetic acid ethyl ester
• 英文别名: α-benzenesulfonyl-(p-methoxyphenyl)acetate；ethyl 4-methoxyphenyl(phenylsulfonyl)acetate；ethyl 2-(benzenesulfonyl)-2-(4-methoxyphenyl)acetate
• CAS: 190672-11-8
• 化学式: C₁₇H₁₈O₅S
• 分子量: 334.393
• InChiKey: QQVSOKCOHXIICX-UHFFFAOYSA-N

物化性质

• 沸点：
  518.4±50.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzenesulfonyl-(4-methoxy-phenyl)-acetic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以62%的产率得到α-benzenesulfonyl-(p-methoxyphenyl)acetic acid
  参考文献：
  名称：

  一些苯磺酸芳基乙酸的新脱羧磺酰化

  摘要：

  摘要 讨论了一些 α-苯磺酰基芳基乙酸与 NaH 在 DMSO 和二甲基二硫醚中反应生成 α-磺酰基化苄基苯砜。

  DOI：

  10.1080/10426500008042091
• 作为产物：
  描述：

  4-溴苯甲醚 、 苯砜乙酸乙酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex sodium hydride 、 三苯基膦 作用下， 以 乙二醇二甲醚 为溶剂， 反应 20.0h， 以41%的产率得到benzenesulfonyl-(4-methoxy-phenyl)-acetic acid ethyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Arylation of Sulfones

  摘要：

  A procedure was developed for monoarylation of sulfones with aryl halides in the presence of palladium complexes. Optimal reaction conditions were found, and the scope of application of the proposed procedure was determined. The arylation occurs only with those sulfones which are relatively strong CH acids, the corresponding monoarylated sulfones are formed in moderate to high yields. The arylation of carbanions derived from the sulfones and some other CH acids requires the presence of an additional equivalent of base. The presence of the latter is also necessary in stoichiometric reactions of carbanions with the palladium complex CF3C6H4Pd(PPh3)(2)Br; no reaction occurs in the absence of a base. A new mechanism of arylation was proposed, where the key stage is deprotonation of palladium intermediate ArPdL2CHXY which activates the reductive elimination stage.

  DOI：

  10.1023/b:rujo.0000044542.70121.04

文献信息

• Formal Aromatic C−H Insertion for Stereoselective Isoquinolinone Synthesis and Studies on Mechanistic Insights into the C−C Bond Formation
  作者：Chan Pil Park、Advait Nagle、Cheol Hwan Yoon、Chiliu Chen、Kyung Woon Jung

  DOI：10.1021/jo9011255

  日期：2009.8.21

  Formal aromatic C−H insertion of rhodium(II) carbenoid was intensively investigated to develop a new methodology and probe its mechanism. Contrasting with the previously proposed direct C−H insertion, the mechanism was revealed to be electrophilic aromatic substitution, which was supported by substituent effects on the aromatic ring and a secondary deuterium kinetic isotope effect. Various isoquinolinones

  深入研究了铑（II）类胡萝卜素的正式芳族CH插入，以开发一种新方法并探讨其机理。与先前提出的直接CH插入相反，该机理被揭示为亲电芳族取代，这是由对芳环的取代基效应和次级氘动力学同位素效应所支持的。通过六元环形成具有高区域和非对映选择性的分子内合成了各种异喹啉酮，同时避免了常见的布氏反应。在分子间，也实现了ho催化富电子芳族化合物上的正式芳族CH插入。
• A New Methodology for Obtaining α-Oxo Ester Equivalents: Sulfanylation of α-Sulfonyl Carboxylic Esters in a Solid/Liquid Phase Transfer Catalytic System
  作者：Blanka Wladislaw、Liliana Marzorati、Nelson Ferreira Claro Junior、Claudio Di Vitta

  DOI：10.1055/s-1997-1212

  日期：1997.4

  A new, convenient procedure for the synthesis of a wide range of α-methylsulfanyl-α-phenylsulfonyl carboxylic esters has been developed and their facile conversion to the corresponding α-oxo esters demonstrated.

  开发了一种新的、方便的合成各种α-甲硫基-α-苯磺酰基羧酸酯的方法，并证明它们可以轻松转化为相应的α-氧代酯。
• Palladium-catalyzed arylation of sulfonyl CH-acids
  作者：Alexander N Kashin、Anton V Mitin、Irina P Beletskaya、Richard Wife

  DOI：10.1016/s0040-4039(02)00321-0

  日期：2002.4

  A method for the palladium-catalyzed monoarylation of a series of functionalized sulfones by aryl halides is described. The reaction proceeds in the presence of 2 mol%, of Pd(2)dba(3)(.)CHCl(3) (dba=dibenzylideneacetone), PPh3 and NaH as a base, only with relatively strong CH-acids and gives monoarylated products in moderate to high yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Arylation of Sulfones
  作者：A. V. Mitin、A. N. Kashin、I. P. Beletskaya

  DOI：10.1023/b:rujo.0000044542.70121.04

  日期：2004.6

  A procedure was developed for monoarylation of sulfones with aryl halides in the presence of palladium complexes. Optimal reaction conditions were found, and the scope of application of the proposed procedure was determined. The arylation occurs only with those sulfones which are relatively strong CH acids, the corresponding monoarylated sulfones are formed in moderate to high yields. The arylation of carbanions derived from the sulfones and some other CH acids requires the presence of an additional equivalent of base. The presence of the latter is also necessary in stoichiometric reactions of carbanions with the palladium complex CF3C6H4Pd(PPh3)(2)Br; no reaction occurs in the absence of a base. A new mechanism of arylation was proposed, where the key stage is deprotonation of palladium intermediate ArPdL2CHXY which activates the reductive elimination stage.
• NEW DECARBOXYLATIVE SULFANYLATION OF SOME PHENYLSULFONYL ARYLACETIC ACIDS
  作者：Blanka Wladislaw、Liliana Marzorati、Claudio Di Vitta、Nelson F. Claro

  DOI：10.1080/10426500008042091

  日期：2000.6.1

  Abstract The reaction of some α-phenylsulfonyl arylacetic acids with NaH in DMSO and dimethyl disulfide leading to α-sulfanylated benzyl phenyl sulfones is discussed.

  摘要 讨论了一些 α-苯磺酰基芳基乙酸与 NaH 在 DMSO 和二甲基二硫醚中反应生成 α-磺酰基化苄基苯砜。