苯乙酸,a-[(4-甲基苯基)磺酰]-,乙基酯 | 104368-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯乙酸,a-[(4-甲基苯基)磺酰]-,乙基酯
• 英文名称: ethyl 2-phenyl-2-tosylacetate
• 英文别名: Ethyl 2-(4-methylphenyl)sulfonyl-2-phenylacetate
• CAS: 104368-08-3
• 化学式: C₁₇H₁₈O₄S
• 分子量: 318.394
• InChiKey: MLJOHNCUVSHPSA-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  489.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯乙酸,a-[(4-甲基苯基)磺酰]-,乙基酯 在 sodium hydroxide 作用下， 生成 1-methyl-4-(benzylsulfonyl)benzene
  参考文献：
  名称：

  Central and peripheral glucocorticoid receptor function in abdominal obesity

  摘要：

  Abdominal obesity seems to be associated with a moderately deranged feedback regulation of the hypothalamic-pituitary-ad renal (HPA) axis where central glucocorticoid receptors (GR) are involved. Therefore, functions of central and peripheral GR were compared in this study. Furthermore, since trinucleotide repeats in early exons of steroid hormone receptor genes influence transcription, and therefore may influence receptor density, this was also studied. Ten middle-aged men, 5 with abdominal obesity and 5 controls, were studied. The suppression of dexamethasone (dex) on serum cortisol was used in dose-response tests to assess the function of central GR. Abdominal adipose tissue biopsies were incubated and exposed to cortisol in different concentrations, and the function of the peripheral GR assayed as induction of lipoprotein lipase (LPL) activity. Aberrant expansion of exonic trinucleotide repeats in the first coding exon of the GR gene was studied by sequencing of genomic DNA. Results showed that men with abdominal obesity showed less inhibition of serum cortisol by dex, particularly at lower concentrations, while in the controls cortisol secretion was inhibited in an apparent dose-response manner. LPL activity in adipose tissue was lower in abdominal obese men than in controls. However, the sensitivity to cortisol was not different between the groups. There was no evidence for expansion of trinucleotide repeats. These results suggest that the central GR and the peripheral GR in adipose tissue exhibit functional differences in abdominal obesity.

  DOI：

  10.1007/bf03343995
• 作为产物：
  描述：

  2-重氮基-2-苯基乙酸乙酯 在 dirhodium tetraacetate 、 lithium aluminium tetrahydride 、 1,3-双(二苯基膦)丙烷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 苯乙酸,a-[(4-甲基苯基)磺酰]-,乙基酯
  参考文献：
  名称：

  通过同时构建两个不同的C–S键， Rh（ii）/膦催化重氮化合物从重氮化合物合成二硫代缩酮衍生物†

  摘要：

  铑（Ⅱ）/膦用硫代磺酸盐作为亚磺酰化剂对α-重氮羰基化合物的双硫化双硫化，通过同时形成分子间和分子内CS键而形成，提供了两个含硫部分。该新方案为原子经济过程中中等至良好的产率提供了快速合成二硫代缩酮衍生物的途径。有人建议通过膦叶立德的形成，然后进行S（O 2）-S键的裂解和重排来进行转化。

  DOI：

  10.1039/c8cc01656a

文献信息

• Revisiting Nucleophilic Substitution Reactions:  Microwave-Assisted Synthesis of Azides, Thiocyanates, and Sulfones in an Aqueous Medium
  作者：Yuhong Ju、Dalip Kumar、Rajender S. Varma

  DOI：10.1021/jo061114h

  日期：2006.8.1

  practical, rapid, and efficient microwave (MW) promoted synthesis of various azides, thiocyanates, and sulfones is described in an aqueous medium. This general and expeditious MW-enhanced nucleophilic substitution approach uses easily accessible starting materials such as halides or tosylates in reaction with alkali azides, thiocyanates, or sulfinates in the absence of any phase-transfer catalyst, and

  在水性介质中描述了实用，快速且有效的微波（MW）促进的各种叠氮化物，硫氰酸盐和砜的合成。这种通用且快速的增强MW的亲核取代方法在不存在任何相转移催化剂的情况下，使用易于获得的起始原料（例如卤化物或甲苯磺酸盐）与碱金属叠氮化物，硫氰酸盐或亚磺酸盐进行反应，并且可以耐受多种反应性官能团。
• Unexpected Role of <i>p</i>-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds
  作者：Jiajia Chen、Wei Guo、Zhenrong Wang、Lin Hu、Fan Chen、Yuanzhi Xia

  DOI：10.1021/acs.joc.6b00844

  日期：2016.7.1

  The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration

  的反应p -toluenesulfonylmethyl胩（TOSMIC）用α-溴代化合物有效地导致α-磺化酮，酯和酰胺的报道，其中TOSMIC作为磺酰化剂的显式的新角色被揭露首次。通过对照实验和DFT计算进行的机理研究表明，该反应是由Cu（OTf）2催化的TosMIC水合引发的，形成了甲酰胺中间体，该中间体在Cs 2 CO 3添加剂的介导下易于进行C-S键裂解。
• Easy access to α-carbonyl sulfones using cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides
  作者：Anup Kumar Sharma、Shiv Chand、Anand Kumar Pandey、Krishna Nand Singh

  DOI：10.1039/d2ob02219b

  日期：——

  Cu-catalyzed cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides is explored to access α-carbonyl sulfones via migratory insertion of Cu-carbene species.

  探索了Cu催化的α-芳基-α-重氮酯与磺酰肼的交叉偶联反应，通过Cu-卡宾物种的迁移插入来访问α-羰基磺酰。
• Adickes, Journal fur praktische Chemie (Leipzig 1954), 1938, vol. <2> 150, p. 81,92
  作者：Adickes

  DOI：——

  日期：——
• <i>N</i>-Sulfonylbenzotriazoles as Advantageous Reagents for <i>C</i>-Sulfonylation
  作者：Alan R. Katritzky、Ashraf A. A. Abdel-Fattah、Anatoliy V. Vakulenko、Hui Tao

  DOI：10.1021/jo051157i

  日期：2005.11.1

  Reactions of readily available N-(alkyl-, aryl-, and heteroarylsulfonyl)benzotriazoles 3a-h with diverse nitriles, reactive heteroaromatics, alkylheteroaromatics, sulfones, and esters produced alpha-cyanoalkyl sulfones 5a-i, sulfonylheteroaromatics 7a-e, alpha-(sulfonylalkyl)heterocycles 9a-f, alpha-sulfonylalkyl sulfones 11a-g, and esters of alpha-sulfonyl acids 14a-c, respectively, in synthetically useful to excellent yields. The results represent the first examples of the successful application of sulfonylazoles for C-sulfonylation.