β-p-tolylsulfanyl-isobutyric acid methyl ester | 30039-20-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: β-p-tolylsulfanyl-isobutyric acid methyl ester
• 英文别名: β-p-Tolylmercapto-isobuttersaeure-methylester；Methyl 2-methyl-3-(4-methylphenyl)sulfanylpropanoate
• CAS: 30039-20-4
• 化学式: C₁₂H₁₆O₂S
• mdl: MFCD12193659
• 分子量: 224.324
• InChiKey: YRNJZWNYAJQLTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲苯二硫醚 、 甲基丙烯酸甲酯 在 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以96%的产率得到β-p-tolylsulfanyl-isobutyric acid methyl ester
  参考文献：
  名称：

  Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds

  摘要：

  A highly practical method to access beta-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. beta-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite (R), as a promoter for the cleavage of disuffides generating thiolate anions that then undergo facile thia-Michael addition to alpha,beta-unsaturated ketones and esters is proposed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.001

文献信息

• Hydroxysulfenylation of Electron-Deficient Alkenes through an Aerobic Copper Catalysis
  作者：Hui Xi、Bicheng Deng、Zhenzhen Zong、Shenglin Lu、Zhiping Li

  DOI：10.1021/acs.orglett.5b00112

  日期：2015.3.6

  A copper-catalyzed hydroxysulfenylation of α,β-unsaturated esters/amides is reported. The method presents a selective and efficient synthesis of β-hydroxysulfides bearing electron-withdrawing groups. The synthetic utility of this method is demonstrated by the concise synthesis of the anticancer drug bicalutamide.

  据报道，铜催化的α，β-不饱和酯/酰胺的羟基亚磺酰基化。该方法提出了具有吸电子基团的β-羟基硫化物的选择性和有效的合成。该方法的合成效用通过抗癌药物比卡鲁胺的简明合成得到证明。
• RYANODINE CHANNEL BINDERS AND USES THEREOF
  申请人：Corey Elias James

  公开号：US20110263569A1

  公开（公告）日：2011-10-27

  Increasing the affinity of calstabin-2 for the cardiac calcium channel RyR2 and thereby stabilizing the channel in the closed state has recently been identified as novel mechanism for treating heart failure, particularly ventricular arrhythmias. JTV-519, a 1,4-benzothiazepine derivative, has been shown to stabilize the calstabin2/RyR2 complex. Novel derivatives of JTV-519 that may be useful in treatment or prevention of heart failure, atrial fibrillation, or exercise-induced cardiac arrhythmias are provided. Synthetic methodology and intermediates in the synthesis of the inventive JTV-519 derivatives are also described.

  增加calstabin-2与心脏钙通道RyR2之间的亲和力，从而稳定通道处于关闭状态，最近被确认为治疗心力衰竭、特别是心室心律失常的新机制。已经证明，1,4-苯并噻唑衍生物JTV-519可以稳定calstabin2/RyR2复合物。提供了JTV-519的新衍生物，这些衍生物可能在治疗或预防心力衰竭、心房颤动或运动引起的心律失常中有用。还描述了创新JTV-519衍生物的合成方法和中间体。
• A Novel Synthesis of β-Arylthio Propanoic Esters Promoted by Low-Valent Titanium
  作者：Daqing Shi、Zaisheng Lu、Lailong Mu、Guiyuan Dai

  DOI：10.1080/00397919808003075

  日期：1998.3.1

  Promoted by low-valent titanium, aryl sulfonyl chlorides react with alpha,beta-unsaturated esters in THF to give beta-arylthio propanoic esters in moderate to good yields.
• US2199799
  申请人：——

  公开号：——

  公开（公告）日：——
• Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds
  作者：Wenxue Guo、Guangshu Lv、Jiuxi Chen、Wenxia Gao、Jinchang Ding、Huayue Wu

  DOI：10.1016/j.tet.2010.02.001

  日期：2010.3

  A highly practical method to access beta-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. beta-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite (R), as a promoter for the cleavage of disuffides generating thiolate anions that then undergo facile thia-Michael addition to alpha,beta-unsaturated ketones and esters is proposed. (C) 2010 Elsevier Ltd. All rights reserved.