methyl 3-(benzoylthio)propanoate | 29651-85-2

• 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 3-(benzoylthio)propanoate
• 英文别名: methyl 3-benzoylsulfanylpropanoate
• CAS: 29651-85-2
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: RZDRJMFQHKAREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3'-二硫代二丙酸二甲酯 、 苯甲酸 在 四(三苯基膦)钯 、 二碳酸二叔丁酯 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 为溶剂， 以84 %的产率得到methyl 3-(benzoylthio)propanoate
  参考文献：
  名称：

  钯催化羧酸和二硫化物便捷合成硫酯

  摘要：

  开发了一种新型的钯催化的由各种羧酸和二硫化物便捷合成硫酯的方法。芳基和烷基羧酸都能够与二芳基或二烷基二硫化物偶联，以中等至良好的产率提供所需的硫酯。该方法的特点是起始原料易于获取且底物范围广泛，为硫酯合成提供了一条实用的路线，无需有毒硫醇或CO气体。

  DOI：

  10.1039/d3nj02972g

文献信息

• Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis
  作者：Maojie Xuan、Chunlei Lu、Meina Liu、Bo-Lin Lin

  DOI：10.1021/acs.joc.9b00500

  日期：2019.6.21

  thioesterification of carboxylic acids with thiols using nontoxic activation agents is highly desirable. Herein, an efficient and practical protocol using safe and inexpensive industrial waste polymethylhydrosiloxane as the activation agent and K3PO4 with 18-crown-6 as a catalyst is described. Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters

  非常需要使用无毒的活化剂将羧酸与硫醇直接硫酯化。在此，描述了一种有效且实用的方案，该方案使用安全且廉价的工业废聚甲基氢硅氧烷作为活化剂，并以18-crown-6作为催化剂的K 3 PO 4。本系统可以耐受羧酸和硫醇取代基上的各种官能团，从而以19-100％的收率提供硫酯。
• Harnessing the catalytic behaviour of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP): An expeditious synthesis of thioesters
  作者：Pallavi Singh、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2017.04.004

  日期：2017.5

  promoting the thiocarbonylation of acyl halides and thiols is disclosed. HFIP was recovered with ease and reused for further reactions without any loss of reactivity. Both aryl and alkyl thiols bearing electron-donating and electron-withdrawing groups as well as aryl- and alkyl acyl halides worked well in this reaction. Inexpensive precursors, short reaction time, obviating workup, high atom economy, and

  已经开发出一种新颖，有效，无金属，无碱和无酸的简单方法来构建有用的硫酯。公开了HFIP促进酰基卤和硫醇的硫羰基化的巨大催化潜力。可以轻松回收HFIP，并重新用于进一步反应，而不会损失任何反应性。带有给电子基团和吸电子基团的芳基和烷基硫醇以及芳基和烷基酰基卤在该反应中均表现良好。廉价的前体，短的反应时间，避免后处理，高原子经济性和克级制备是发达的硫醇S-羰基化生态友好路线的重要特征。
• Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols
  作者：Pallavi Singh、Rama Krishna Peddinti

  DOI：10.1007/s12039-020-01871-5

  日期：2021.3

  Abstract An unprecedented metal-, halogen- and solvent-free, MSAA-promoted S-carbonylation of thiols with feedstock acids has been developed. This new transformation provides an efficient and atom-economic strategy for the synthesis of thioesters in a single operation from readily available and inexpensive starting materials. The reaction avoids the use of expensive and hazardous coupling reagents

  摘要 已经开发了前所未有的无金属，无卤素和无溶剂，MSAA促进的硫醇与原料酸的S-羰基化反应。这种新的转变为从容易获得和廉价的起始原料一次合成硫酯提供了有效且原子经济的策略。该反应避免了使用昂贵且危险的偶联剂，碱，并且仅将水作为副产物生成，因此使该化学合成过程更加可行，对环境友好，并有助于实现可持续的化学反应。 图形摘要
• Synthesis of S-functionalized thioesters using thioaroylate ions derived from carboxylic acids and tetrathiomolybdate via acyloxyphosphonium intermediates
  作者：Purushothaman Gopinath、Chanda Debasree、Ravindran Sasitha Vidyarini、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2010.06.028

  日期：2010.8

  Thioaroylate ions generated in situ from acyloxyphosphonium salts and tetrathiomolybdate upon Michael addition or ring opening of three membered systems led to a facile synthesis of S-functionalized thioesters. While the ring opening of aziridines gave very good yield of the products, Michael addition and epoxide ring opening gave moderate yields.

  在三元体系的迈克尔加成或开环后，由酰氧基phosph盐和四硫代钼酸盐原位产生的硫代芳族酸酯离子导致了S-官能化硫酯的简便合成。尽管氮丙啶的开环给出了非常好的产物收率，但是迈克尔加成和环氧化物的开环给出了中等收率。
• Thioesterifications Free of Activating Agent and Thiol: A Three-Component Reaction of Carboxylic Acids, Thioureas, and Michael Acceptors
  作者：Sharada Prasanna Swain、Yen-Lin Chou、Duen-Ren Hou

  DOI：10.1002/adsc.201500426

  日期：2015.8.24

  from carboxylic acids, thioureas, and Michael acceptors is described. This process was further improved by use of 1‐[2‐(methylamino)ethyl]‐3‐phenylthiourea (4) as the catalyst. Aromatic and aliphatic carboxylic acids with functional groups are compatible with this process, and both α,β‐unsaturated esters and ketones can be the Michael acceptors for this reaction. The progress of this reaction was monitored

  描述了直接从羧酸，硫脲和迈克尔受体进行胺催化的一锅法合成硫酯的方法。通过使用1- [2-（甲基氨基）乙基] -3-苯基硫脲（4）作为催化剂，可进一步改善此过程。具有官能团的芳族和脂肪族羧酸与该过程兼容，并且α，β-不饱和酯和酮均可为该反应的迈克尔受体。通过1 H NMR监测该反应的进行，并提出了反应机理。