thioacetic acid S-(4-carboxybenzyl) ester | 132035-64-4

• 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: thioacetic acid S-(4-carboxybenzyl) ester
• 英文别名: 4-(acetylthiomethyl)benzoic acid；4-[(Acetylsulfanyl)methyl]benzoic acid；4-(acetylsulfanylmethyl)benzoic acid
• CAS: 132035-64-4
• 化学式: C₁₀H₁₀O₃S
• 分子量: 210.254
• InChiKey: QKTURUWIOATPBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-(4-carboxybenzyl) ester 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 methyl 4-(mercaptomethyl)benzoate
  参考文献：
  名称：

  Luminescent ‘On-Off’ CdSe/ZnS Quantum Dot Chemodosimeter for Hydroxide Based on Photoinduced Electron Transfer from a Carboxylate Moiety

  摘要：

  一个CdSe-ZnS量子点（QD）通过与三步合成的对巯基甲基苯甲酸酯进行位替换反应进行表面功能化。所得到的荧光团-连接体-受体QD结合物通过红外光谱、紫外-可见光谱和荧光光谱进行了表征。QD的发射特征显示在542 nm处有一个狭窄的发射峰。向含QD结合物的溶液中添加氢氧化物会导致原始荧光的淬灭，认为这是由于电子丰富的苯甲酸酯基团向QD价带的光诱导电子转移反应。这是首次报告的由芳基羧酸根基团导致CdSe-ZnS QD发光的荧光淬灭现象。

  DOI：

  10.1007/s10895-013-1212-z
• 作为产物：
  描述：

  对甲基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 甲醇 、 氯苯 为溶剂， 反应 49.0h， 生成 thioacetic acid S-(4-carboxybenzyl) ester
  参考文献：
  名称：

  Luminescent ‘On-Off’ CdSe/ZnS Quantum Dot Chemodosimeter for Hydroxide Based on Photoinduced Electron Transfer from a Carboxylate Moiety

  摘要：

  一个CdSe-ZnS量子点（QD）通过与三步合成的对巯基甲基苯甲酸酯进行位替换反应进行表面功能化。所得到的荧光团-连接体-受体QD结合物通过红外光谱、紫外-可见光谱和荧光光谱进行了表征。QD的发射特征显示在542 nm处有一个狭窄的发射峰。向含QD结合物的溶液中添加氢氧化物会导致原始荧光的淬灭，认为这是由于电子丰富的苯甲酸酯基团向QD价带的光诱导电子转移反应。这是首次报告的由芳基羧酸根基团导致CdSe-ZnS QD发光的荧光淬灭现象。

  DOI：

  10.1007/s10895-013-1212-z

文献信息

• Synthesis of tetranuclear iron–sulphur protein analogues with tetrathiol ligands attached to macrocycles which provide intramolecular hydrophobic domains
  作者：Hiroaki (Yohmei) Okuno、Kouichi Uoto、Takenori Tomohiro、Marie-Thérèse Youinou

  DOI：10.1039/dt9900003375

  日期：——

  iron-sulphur proteins is introduced, where the active site core is surrounded by an intramolecular hydrophobic domain formed by a 36-membered ring consisting of a methylene backbone. An efficient synthesis of the macrocyclic ligands 1,10,19,28-tetra(4-mercaptobenzoyl)-1,10,19,28-tetra-azacyclohexatriacontane, 1,10,19,28-[4-(mercaptomethyl)benzoyl]-1,10,19,28-tetra-azacyclohexatriacontane and 1,10,19

  一种新型的4Fe–4S铁硫蛋白的活性位点类似物被引入，其中活性位点的核心被分子内的疏水域包围，该分子域由由亚甲基骨架组成的36元环形成。大环配体1,10,19,28-四（4-巯基苯甲酰基）-1,10,19,28-四氮杂环六三aco烷，1,10,19,28- [4-（巯基甲基）苯甲酰基]的有效合成描述了-1,10,19,28-四氮杂环六三aco烷和1,10,19,28-四-（3-巯基-3-甲基丁酰基）-1,10,19,28-四氮杂环六cyclo烷。他们与[Fe 4 S 4（SBu t）4 ] 2–的反应以mp> 300°C的黑色粉末的形式提供了具有良好收率（70–90％）的新型簇。它们溶于二甲基甲酰胺，二甲基亚砜和碳酸亚丙酯。Fe 4 S 4团簇的络合物形成主要通过紫外可见和nmr研究证明，并对新团簇的性质进行了讨论。
• Geometric Control of a Pyridoxal-Catalyzed Aldol Condensation
  作者：John T. Koh、Lionel Delaude、Ronald Breslow

  DOI：10.1021/ja00104a004

  日期：1994.12

  A chiral cyclophane derivative of pyridoxal has been synthesized that has amino groups oriented specifically over one face of the cofactor. The compound catalyzes the formation of threonine and allo-threonine from glycine and acetaldehyde with enantioinductions that are a function of pH, reversing the optical selectivity between low pH and high pH. The stereochemical results are compared with those of structurally related pyridoxal cyclophanes that lack titratable catalytic groups. Explanations are advanced for this stereochemical reversal and for the otherwise surprising preference of most of these compounds to react on the more hindered face of the pyridoxal. Models indicate that the transamination intermediate is distorted by the transannular chain, and stereoelectronic arguments predict that this distortion should lead to reaction on the face that carries the chain, as observed. The stereochemical reversal with the attached (dimethylamino)alkyl group, as a function of pH, may reflect catalysis by the protonated form, but metal coordination by the basic form cannot be excluded.
• Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties
  作者：Boon-Saeng Park、William Widger、Harold Kohn

  DOI：10.1016/j.bmc.2005.07.075

  日期：2006.1

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.
• Cruciform π-Systems for Molecular Electronics Applications
  作者：Jennifer E. Klare、George S. Tulevski、Kenji Sugo、Anat de Picciotto、Kiley A. White、Colin Nuckolls

  DOI：10.1021/ja0350942

  日期：2003.5.1

  This study details a modular and general synthesis of a new class of molecules consisting of cruciform pi-systems. The key to synthesizing these molecules was an unprecedented double Staudinger cyclization. Once formed, these rigid compounds assemble into ordered monolayer films on metal and metal oxide surfaces to orient their conjugated, bis-phenyloxazole subunits upright. This surface orientation is enforced by the external phenyl substituents that are out of the ring plane, thus preventing the prone conformation.
• COMPOSES BI-AROMATIQUES ET LEUR UTILISATION EN MEDECINE HUMAINE ET VETERINAIRE ET EN COSMETIQUE
  申请人：CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES GALDERMA - CIRD GALDERMA

  公开号：EP0552282A1

  公开（公告）日：1993-07-28