methyl bromobenzenethiocarboxylate | 4906-32-5

• 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: methyl bromobenzenethiocarboxylate
• 英文别名: S-methyl 4-bromobenzothioate；S-methyl p-bromobenzothioate；S-methyl-4-bromobenzothioate；4-Brom-thiobenzoesaeure-S-methylester；4-Brom-thiobenzoesaeure-methylester；S-methyl p-bromobenzothioat；S-methyl 4-bromobenzenecarbothioate
• CAS: 4906-32-5
• 化学式: C₈H₇BrOS
• 分子量: 231.113
• InChiKey: REIWMZNDMAMYSD-UHFFFAOYSA-N

物化性质

• 熔点：
  34 °C
• 沸点：
  102-104 °C(Press: 3 Torr)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl bromobenzenethiocarboxylate 在 sodium hydroxide 作用下， 反应 1.0h， 以59%的产率得到4-溴苯甲酸
  参考文献：
  名称：

  Aromatic substitution. 46. Methyl (ethyl) thio(dithio)carboxylation of aromatics with S-methyl(5-ethyl)thiocarboxonium and -dithiocarboxonium fluoroantimonates

  摘要：

  DOI：

  10.1021/jo00315a040
• 作为产物：
  描述：

  硫氰酸甲酯 、 4-溴苯甲酸 在 三氟乙酸 作用下， 反应 2.0h， 以67%的产率得到methyl bromobenzenethiocarboxylate
  参考文献：
  名称：

  Reaction of para-substituted aromatic acids with methyl thiocyanate in trifluoroacetic acid

  摘要：

  We have investigated the reactions of aromatic carboxylic acids (p-XC6H4COOH, in which X = F, Cl, Br, I, NO2, CH3, H, OCH3) with methyl thiocyanate in trifluoroacetic acid. It was shown that the starting acids are converted to S-methyl benzothioates [p-XC6H4COSCH3 (40-70%)] and the nitrile of the acid [p-XC6H4CN (20-50%)]. In addition to starting acid, in the reaction mixtures products of the reaction of CF3COOH with methyl thiocyanate were identified.

  DOI：

  10.1007/bf00869524

文献信息

• Synthesis of β-Amino-α,β-unsaturated Ketone Derivatives via Sequential Rhodium-Catalyzed Sulfur Ylide Formation/Rearrangement
  作者：Jun He、Zengming Man、Yinping Shi、Chuan-Ying Li

  DOI：10.1021/acs.joc.5b00521

  日期：2015.5.1

  a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.

  在Rh（II）催化剂和β-（甲硫基）-α，β-不饱和酮的存在下，可以将1-磺酰基-1,2,3-三唑转化为官能化的β-氨基-α，β-不饱和酮通过形成α-亚氨基铑卡宾/叶立德和随后的重排。该产物可方便地以高产率分解为有用的2-甲基硫代吡咯衍生物。
• [EN] FLUOROISOQUINOLINE SUBSTITUTED THIAZOLE COMPOUNDS AND METHODS OF USE<br/>[FR] THIAZOLES SUBSTITUÉS PAR FLUOROISOQUINOLÉINE ET LEURS MÉTHODES D'APPLICATION
  申请人：AMGEN INC

  公开号：WO2010083246A1

  公开（公告）日：2010-07-22

  The invention relates to thiazole compounds of Formula (I) and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such thiazole compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.

  该发明涉及式(I)的噻唑化合物及其组合物，用于治疗由蛋白激酶B（PKB）介导的疾病，其中变量具有此处提供的定义。该发明还涉及在治疗与异常细胞生长、癌症、炎症和代谢紊乱相关的疾病状态中使用这种噻唑化合物和其组合物的治疗用途。
• Palladium Catalyzed Direct Carbonylative Thiomethylation of Aryldiazonium Salts and Amines with 4-(Methylthio)-2-Butanone as (Methylthio) Transfer Agent
  作者：Qingqiang Tian、Shasha Xu、Chiying Zhang、Xinyi Liu、Xiangwei Wu、Yahui Li

  DOI：10.1021/acs.joc.1c00665

  日期：2021.7.2

  Herein, an interesting palladium-catalyzed procedure for the direct carbonylative thiomethylation of aromatic amine derivatives with 4-methylthio-2-butanone is developed. Using 4-methylthio-2-butanone as (methylthio) transfer agent, a variety of corresponding thioesters are obtained with moderate to good yields under base-free condition. In addition, good functional group tolerance can be observed

  在此，开发了一种有趣的钯催化方法，用于芳胺衍生物与 4-甲硫基-2-丁酮的直接羰基化硫甲基化。使用4-甲硫基-2-丁酮作为（甲硫基）转移剂，在无碱条件下以中等至良好的收率获得了多种相应的硫酯。此外，可以观察到良好的官能团耐受性。
• Olah,G.A.; Schilling,P., Justus Liebigs Annalen der Chemie, 1972, vol. 761, p. 77 - 94
  作者：Olah,G.A.、Schilling,P.

  DOI：——

  日期：——
• OLAH G. A.; BRUCE M. R.; CLOUET F. L., J. ORG. CHEM., 1981, 46, NO 2, 438-442
  作者：OLAH G. A.、 BRUCE M. R.、 CLOUET F. L.

  DOI：——

  日期：——