苯乙硫酸,S-乙基酯 | 14476-63-2

• 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: 苯乙硫酸,S-乙基酯
• 英文名称: ethyl phenylthioacetate
• 英文别名: S-ethyl 2-phenylethanethioate
• CAS: 14476-63-2
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: IMCBPLIREFBOKS-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  102-104 °C(Press: 3 Torr)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  苯乙硫酸,S-乙基酯 在 双(三-o-甲苯磷)钯(0) 作用下， 以 对二甲苯 为溶剂， 以50%的产率得到苄基乙基硫醚
  参考文献：
  名称：

  Palladium- and Nickel-Catalyzed Decarbonylative C–S Coupling to Convert Thioesters to Thioethers

  摘要：

  This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.

  DOI：

  10.1021/acs.orglett.7b03305
• 作为产物：
  描述：

  (1-Ethylsulfanyl-2-phenyl-ethyl)-phosphonic acid diethyl ester 在 正丁基锂 、 氧气 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到苯乙硫酸,S-乙基酯
  参考文献：
  名称：

  基于膦酸碳负离子的氧化合成单和1,4-二羰基化合物。二氢茉莉酮，烯丙酮和甲基新霉素b的合成

  摘要：

  发现α-烷硫基取代的膦酸酯碳负离子的氧化得到相应的羰基化合物。描述了涉及膦酸碳负离子的氧化作为关键步骤的1,4-二羰基系统的新合成。报道了二氢茉莉酮和烯丙酮的全合成和甲基新霉素B的正式合成。

  DOI：

  10.1016/s0040-4039(01)81212-0

文献信息

• Synthetic Strategies for the Synthesis and Transformation of Substituted Pyrrolinones as Advanced Intermediates for Rhazinilam Analogues
  作者：Inga Kholod、Olivier Vallat、Ana-Maria Buciumas、Antonia Neels、Reinhard Neier

  DOI：10.1002/ejoc.201402903

  日期：2014.12

  The biaryl core structure of rhazinilam with its fixed dihedral angle is a pivotal element for its unique in vitro cytotoxic activity. Most of the related natural products are oxidized versions of rhazinilam. Replacing the sensitive pyrrole ring by a pyrrolinone ring is the basis of our initial strategy towards rhazinilam analogues. With this goal, variants of the sequence crossed Mukaiyama aldol reaction

  具有固定二面角的 rhazinilam 的联芳核心结构是其独特的体外细胞毒活性的关键因素。大多数相关的天然产物是氧化形式的 rhazinilam。用吡咯啉酮环代替敏感的吡咯环是我们对罗嗪类似物的初步策略的基础。为了这个目标，研究了与向山羟醛反应和施陶丁格反应交叉的序列变体。将适当取代的苯乙酮与 O-甲基 O-三甲基甲硅烷基乙烯酮缩醛反应以良好至极好的产率得到吡咯啉酮 8a 和 8b。这些中间体可以通过四个高产率步骤转化为吡咯前体 7a-c，其中包含构建 rhazinilam 环 A、B 和 C 所需的所有原子。我们的研究表明这些中间体缺乏稳定性。描述了针对该中心联芳基核结构的替代合成方法。
• Heterocyclic compounds as P2X7 ion channel blockers
  申请人：Shum Patrick

  公开号：US20050026916A1

  公开（公告）日：2005-02-03

  The present invention relates to a novel series of 4,5-diphenyl-2-amino-4,5-dihydro-imidazole derivatives of the formula II: wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , X and Y are as defined herein. This invention also relates to methods of making these compounds. The compounds of this invention are P2X7 ion channel blockers and are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases having an inflammatory component, including inflammatory bowel disease, rheumatoid arthritis and disease conditions associated with the central nervous system, such as stroke, Alzheimer's disease, etc.

  本发明涉及一种新的4,5-二苯基-2-氨基-4,5-二氢咪唑衍生物系列，其化学式为II： 其中R、R1、R2、R3、R4、R5、X和Y如本文所定义。本发明还涉及制备这些化合物的方法。本发明的化合物是P2X7离子通道阻断剂，因此在作为药用剂方面具有用途，特别是在治疗和/或预防具有炎症成分的各种疾病方面，包括炎症性肠病、类风湿关节炎以及与中枢神经系统相关的疾病状况，如中风、阿尔茨海默病等。
• [EN] PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE DERIVATIVES AS PDE9 INHIBITORS<br/>[FR] UTILISATION DE DÉRIVÉS DE PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE COMME INHIBITEURS DE PDE9
  申请人：CELON PHARMA SA

  公开号：WO2014016789A1

  公开（公告）日：2014-01-30

  A compound of the general formula (I) wherein R1 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, CN, -O-C1-C3-alkyl, fluorinated -O-C1-C3-alkyl, -(CH2)mOH and 5-membered heterocyclic group with 1 or 2 heteroatoms selected from N, O and S; and 6- or 10-membered heteroaryl with 1 to 3 heteroatoms selected from O, N and S; R2 and R3 independently of each other represent H atom or straight or branched C1-C3 alkyl; R4 is selected from the group consisting of 4- to 6- membered cycloalkyl, wherein one of carbon atoms can be replaced by O atom, and which is unsubstituted or substituted with one or two halogen atoms,and straight or branched C1-C4 alkyl; Q represents a bond or C1-C3-alkylene, which can be optionally substituted by one to three C1-C3-alkyls; X is selected from the group consisting of O, NR5, and S(O)p; R5 represents H atom or C1-C3alkyl; m is 1, 2 or 3; p is 0, 1 or 2; and salts thereof, for use as a medicament, in particular for treating cognitive function disorders and neurodegenerative diseases.

  通用式（I）的化合物，其中R1选自苯基未取代或取代的基团，所取代基团可为1至3个取自F、Cl、Br、I、CN、-O-C1-C3-烷基、氟代-O-C1-C3-烷基、-(CH2)mOH和含有1或2个取自N、O和S的杂原子的5元杂环基；以及含有1至3个取自O、N和S的杂原子的6-或10-元杂芳基；R2和R3彼此独立地代表H原子或直链或支链的C1-C3烷基；R4选自4-至6-环脂肪族基团，其中一个碳原子可被氧原子取代，未取代或取代有一或两个卤素原子，以及直链或支链的C1-C4烷基；Q代表键或C1-C3-亚烷基，可选择性地被1至3个C1-C3-烷基取代；X选自O、NR5和S(O)p的基团；R5代表H原子或C1-C3烷基；m为1、2或3；p为0、1或2；以及其盐，用作药物，特别用于治疗认知功能障碍和神经退行性疾病。
• Phosphodiesterase inhibitors
  申请人：LES LABORATOIRES BEECHAM S.A.

  公开号：EP0381374A1

  公开（公告）日：1990-08-08

  A compound of formula (I), or a pharmaceutically acceptable salt thereof: in which, R₁ is hydrogen, C₁₋₆ alkyl or CH₂OR₆; R₂ is hydrogen or C₁₋₆ alkyl; R₃ is hydrogen or C₁₋₆ alkyl; each of W and Z, which are different, represents -CR₄R₅- or -(CRxRy)n-, in which, R₄ is hydrogen, C₁₋₃ alkyl, C₁₋₃ alkylthio, C₁₋₃ alkoxy or C₁₋₆ alkyl phenyl; R₅ is C₁₋₃ alkyl, C₁₋₃ alkylthio, C₁₋₃ alkoxy, phenyl, substituted phenyl, C₃₋₆ cycloalkyl, phenylthio, C₁₋₆ alkyl phenyl, halo-substituted benzyl, or heteroaryl; or together R₄ and R₅ form a 3 to 6 membered carbocyclic ring, or a heterocyclic ring containing one or two ring oxygen, nitrogen or sulphur atoms, or R₄ and R₅ together form an oxo or methylene group; each of Rx and Ry is hydrogen or C₁₋₃ alkyl; n is zero or 1; R₆ is phenyl substituted aminocarbonyl, C₁₋₆ alkoxy carbonyl-C₁₋₆ alkyl, phenyl-C₁₋₆ alkyl, phenyl, C₃₋₆ cycloalkylcarbonyl, C₃₋₆ cycloalkylcarbonyl-C₁₋₆ alkyl, C₃₋₆ cycloalkyl C₁₋₆ alkyl; C₁₋₆ alkylthiocarbonyl; halo-substituted C₁₋₆ alkoxycarbonyl; C₁₋₆ alkoxy C₁₋₆ alkyleneoxycarbonyl; C₁₋₆ alkylthio C₁₋₆ alkyleneoxycarbonyl; C₁₋₆ alkoxythiocarbonyl; C₃₋₆ cycloalkyloxycarbonyl; cyano substituted C₁₋₆ alkoxycarbonyl; di-C₁₋₆ alkylphosphonate; C₁₋₆ alkenyloxycarbonyl; or R₆ is hydrogen when R₅ is phenyl, C₃₋₆ cycloalkyl, phenylthio, C₁₋₆ alkylphenyl or halo-substituted benzyl; R₆ is benzoyl or aminobenzoyl when R₄ and R₅ form a C₃₋₆ cycloalkyl ring; R₇ is hydrogen, C₁₋₆ alkyl or halogen; X is oxygen or sulphur; and A is sulphur, oxygen or -NH-, is useful for the treatment of heart disease.

  式（I）的化合物，或其药学上可接受的盐：其中，R₁为氢，C₁₋₆烷基或CH₂OR₆；R₂为氢或C₁₋₆烷基；R₃为氢或C₁₋₆烷基；W和Z中的每一个，它们不同，代表-CR₄R₅-或-(CRxRy)n-，其中，R₄为氢，C₁₋₃烷基，C₁₋₃烷基硫，C₁₋₃烷氧基或C₁₋₆烷基苯基；R₅为C₁₋₃烷基，C₁₋₃烷基硫，C₁₋₃烷氧基，苯基，取代苯基，C₃₋₆环烷基，苯硫基，C₁₋₆烷基苯基，卤代苄基或杂环烷基；或者R₄和R₅一起形成3到6成员的碳环，或者含有一个或两个环氧原子、氮原子或硫原子的杂环；或者R₄和R₅一起形成氧或亚甲基基团；Rx和Ry中的每一个为氢或C₁₋₃烷基；n为零或1；R₆为苯基取代氨基甲酰基，C₁₋₆烷氧基甲酰基-C₁₋₆烷基，苯基-C₁₋₆烷基，苯基，C₃₋₆环烷基甲酰基，C₃₋₆环烷基甲酰基-C₁₋₆烷基，C₃₋₆环烷基C₁₋₆烷基；C₁₋₆烷基硫代甲酰基；卤代C₁₋₆烷氧基甲酰基；C₁₋₆烷氧基-C₁₋₆烷基氧基甲酰基；C₁₋₆烷基硫基-C₁₋₆烷基氧基甲酰基；C₁₋₆烷氧基硫代甲酰基；C₃₋₆环烷氧基甲酰基；氰基取代C₁₋₆烷氧基甲酰基；二C₁₋₆烷基膦酸酯；C₁₋₆烯氧基甲酰基；或者当R₅为苯基，C₃₋₆环烷基，苯硫基，C₁₋₆烷基苯基或卤代苄基时，R₆为氢；当R₄和R₅形成C₃₋₆环烷基环时，R₆为苯甲酰基或氨基苯甲酰基；R₇为氢，C₁₋₆烷基或卤素；X为氧或硫；A为硫，氧或-NH-，用于治疗心脏病。
• Highly Efficient Iron(II) Chloride/N-Bromosuccinimide-Mediated Synthesis of Imides and Acylsulfonamides
  作者：Feng Wang、Hongxia Liu、Hua Fu、Yuyang Jiang、Yufen Zhao

  DOI：10.1002/adsc.200800668

  日期：2009.1

  We have developed a general and highly efficient iron(II) chloride/N-bromosuccinimide (NBS)-mediated method for the synthesis of imides and acylsulfonamides via couplings of thioesters with carboxamides/sulfonamides, and the method is simple, economical and shows practical advantages.

  我们已经开发了一种通用且高效的氯化铁（II）/ N-溴琥珀酰亚胺（NBS）介导的方法，该方法通过硫代酯与羧酰胺/磺酰胺的偶联来合成酰亚胺和酰磺酰胺，该方法简单，经济且具有实际优势。