methyl mercaptoacetate | 7337-23-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl mercaptoacetate
• 英文别名: Mercaptomethyl acetate；sulfanylmethyl acetate
• CAS: 7337-23-7
• 化学式: C₃H₆O₂S
• 分子量: 106.145
• InChiKey: SIMUSDODLAXNBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯丙炔酸甲酯 、 methyl mercaptoacetate 在 哌啶 、 乙醇 作用下， 以55%的产率得到methyl (Z)-3-(methoxycarbonylmethylthio)cinnamate
  参考文献：
  名称：

  巯基乙酸甲酯碱催化加成到乙炔酮和酯的立体化学。活化基团和溶剂的影响

  摘要：

  哌啶催化巯基乙酸甲酯与乙醇中的苯甲酰基-和对-氯苯甲酰基-苯基乙炔的加成得到相应的(Z)-1-芳基-3-(甲氧羰基甲硫基)-3-苯基-2-丙烯-1-酮。然而，对苯异酰基苯基乙炔以 4:1 的比例得到 (Z)- 和 (E)-3-(甲氧基羰基甲硫基)-1-(对甲氧基苯基)-3-苯基-2-丙烯-1-酮的混合物. 当后者在无水苯中添加时，该比例完全颠倒。这些结果的合理化取决于活化基团和溶剂对加成立体化学的影响。哌啶催化巯基乙酸甲酯与乙醇中的苯丙酸甲酯的加成得到(Z)-3-(甲氧基羰基甲硫基)肉桂酸甲酯。水合肼将一些上述单加合物转化为一些吡唑衍生物。

  DOI：

  10.1246/bcsj.53.1739

文献信息

• N-Heterocyclic carbene-catalyzed stereoselective construction of olefinic carbon–sulfur bonds via cross-coupling reaction of gem-difluoroalkenes and thiols
  作者：Zi-Song Cong、Yang-Guo Li、Lei Chen、Fen Xing、Guang-Fen Du、Cheng-Zhi Gu、Lin He

  DOI：10.1039/c7ob00599g

  日期：——

  forming reaction was developed. Under the catalysis of 10 mol% stable N-heterocyclic carbene, thiols undergo direct nucleophilic substitution reaction with gem-difluoroalkenes to produce α-fluorovinyl thioethers in high yields with excellent Z-selectivity. In this process, bases are not necessary.

  开发了一种新型的有机催化烯烃碳硫键形成反应。在10摩尔％稳定的N杂环卡宾的催化下，硫醇与宝石-二氟烯烃进行直接亲核取代反应，以高收率和优异的Z-选择性生产α-氟乙烯基硫醚。在此过程中，不需要碱。
• COMPOUNDS FOR TREATING PROLIFERATIVE DISORDERS
  申请人：Wang Shudong

  公开号：US20130190325A1

  公开（公告）日：2013-07-25

  A compound of formula (I) or a pharmaceutically acceptable salt or solvate or physiologically hydrolysable, solubilising or immobilisable derivative thereof; wherein: any one or two of X., X2 and X3 is a N atom and the remaining two or one of X 1 , X 2 and X 3 are independently CR 13 ; Y is selected from SO 2 and SO; R 1 , R 2 , R 3 , and R 7 and the one or two R 13 groups are each independently selected from H and R 10 , R 10 is selected from R 8 , alkyl, aryl, heteroaryl and combinations of two or more thereof and combinations with one or more R 9 , or R 10 is one or more moieties R 11 Sinking one or more alkyl, alkoxy, aryl, heteroaryl or R 8 or R 9 groups or combinations thereof, directly or via a moiety selected from alkylene, arylene, heteroarylene or combinations thereof, wherein alkyl, aryl, heteroaryl groups or moieties thereof may be substituted with one or more groups R 12 , or R 10 is selected from a group R 12 ; R 11 is selected from 0-, N—, NH—, N═C, CO—, C00-, CON—, CONH—, S0 2 -, S0 2 N—, S0 2 NH—; R 12 is selected from halogen, NH 2 , N0 2 , CN, OH, COOH, CONH 2 , C(═NH)NH 2 , S0 3 H, S0 2 NH 2 , S0 2 CH 3 , OCH 3 , OCH 2 CH 3 , CF 3 ; R 8 and R 9 comprise one or more solubilising moieties independently chosen from i) neutral hydrophilic groups, ii) ionisable organic acids, iii) ionisable organic bases, iv} chemical functions or moieties providing covalent or non-covalent attachment or binding to a solid phase or an immobile receptor and combinations thereof; R 4 , R 5 and R 6 are each independently selected from H and R 10 , or two of R 4 to R 6 are linked to form a cyclic ether or amine containing one or more additional oxygen or nitrogen atoms. The compound may be used for treating a condition mediated by one or more enzymes selected from AKT, Aurora kinase, BCR-ABL, CDK, FLT, GSK3, IKK, JAK, MAPK, PDGF, PI3K, PKA, PKB, PKC, PLK, Src and VEGF family enzymes, or for treating cancer or other proliferative disorder, or for inhibiting growth of cancer cells, or for inducing apoptosis of cancer cells, in a human or animal subject.

  公式（I）的化合物，或其药学上可接受的盐或溶剂或生理水解、溶解或固定化衍生物；其中：X、X2和X3中的任意一个或两个是N原子，其余两个或一个是独立的CR13；Y从SO2和SO中选择；R1、R2、R3和R7以及一个或两个R13基团各自独立地选择自H和R10，R10从R8、烷基、芳基、杂环芳基和两种或两种以上的组合以及与一个或多个R9的组合中选择，或者R10是一个或多个基团R11，其中每个基团R11包含一个或多个烷基、烷氧基、芳基、杂环芳基或R8或R9基团或其组合，直接或通过选择自烷基、芳基、杂环芳基或其组合的基团连接，其中烷基、芳基、杂环芳基基团或其基团可以被一个或多个基团R12取代，或者R10从一个基团R12的群中选择；R11从0-、N-、NH-、N═C、CO-、C00-、CON-、CONH-、S02-、S02N-、S02NH-中选择；R12从卤素、NH2、N02、CN、OH、COOH、CONH2、C（═NH）NH2、S03H、S02NH2、S02CH3、OCH3、OCH2CH3、CF3中选择；R8和R9各自包括一个或多个溶解化基团，独立地选择自i）中性亲水基团、ii）可离子化有机酸、iii）可离子化有机碱、iv）化学功能或基团，提供共价或非共价的固定或结合到固定相或不动的受体上，以及它们的组合；R4、R5和R6各自独立地选择自H和R10，或者R4到R6中的两个被连接形成含有一个或多个额外氧或氮原子的环醚或胺。该化合物可用于治疗由AKT、Aurora激酶、BCR-ABL、CDK、FLT、GSK3、IKK、JAK、MAPK、PDGF、PI3K、PKA、PKB、PKC、PLK、Src和VEGF家族酶中的一个或多个酶介导的疾病，或用于治疗癌症或其他增生性疾病，或用于抑制癌细胞的生长，或用于诱导癌细胞凋亡，在人类或动物主体中。
• Compounds for treating proliferative disorders
  申请人：Wang Shudong

  公开号：US08829003B2

  公开（公告）日：2014-09-09

  A compound of formula (I) or a pharmaceutically acceptable salt or solvate or physiologically hydrolysable, solubilizing or immobilizable derivative thereof; wherein: any one or two of X., X2 and X3 is a N atom and the remaining two or one of X1, X2 and X3 are independently CR13; Y is selected from SO2 and SO; R1, R2, R3, and R7 and the one or two R13 groups are each independently selected from H and R10, R10 is selected from R8, alkyl, aryl, heteroaryl and combinations of two or more thereof and combinations with one or more R9, or R10 is one or more moieties R11 Sinking one or more alkyl, alkoxy, aryl, heteroaryl or R8 or R9 groups or combinations thereof, directly or via a moiety selected from alkylene, arylene, heteroarylene or combinations thereof, wherein alkyl, aryl, heteroaryl groups or moieties thereof may be substituted with one or more groups R12, or R10 is selected from a group R12; R11 is selected from 0-, N—, NH—, N═C, CO—, C00-, CON—, CONH—, S02-, S02N—, S02NH—; R12 is selected from halogen, NH2, N02, CN, OH, COOH, CONH2, C(═NH)NH2, S03H, S02NH2, S02CH3, OCH3, OCH2CH3, CF3; R8 and R9 comprise one or more solubilizing moieties independently chosen from i) neutral hydrophilic groups, ii) ionisable organic acids, iii) ionisable organic bases, iv} chemical functions or moieties providing covalent or non-covalent attachment or binding to a solid phase or an immobile receptor and combinations thereof; R4, R5 and R6 are each independently selected from H and R10, or two of R4 to R6 are linked to form a cyclic ether or amine containing one or more additional oxygen or nitrogen atoms. The compound may be used for treating a condition mediated by one or more enzymes selected from AKT, Aurora kinase, BCR-ABL, CDK, FLT, GSK3, IKK, JAK, MAPK, PDGF, PI3K, PKA, PKB, PKC, PLK, Src and VEGF family enzymes, or for treating cancer or other proliferative disorder, or for inhibiting growth of cancer cells, or for inducing apoptosis of cancer cells, in a human or animal subject.

  式（I）的化合物，或其药学上可接受的盐、溶剂或生理水解、溶解或固定衍生物；其中：X、X2和X3中的任意一个或两个是N原子，剩下的两个或一个是独立的CR13；Y选自SO2和SO；R1、R2、R3、R7和一个或两个R13基团各自独立地选自H和R10，R10选自R8、烷基、芳香族、杂环芳香族和两种或以上的组合物以及与一个或多个R9的组合物，并且R10是一个或多个基团R11，其中每个基团R11包括一个或多个烷基、烷氧基、芳香族、杂环芳香族或R8或R9基团或其组合物，直接或通过选自烷基、芳基、杂环芳基或其组合物的基团与之相连，其中烷基、芳香族、杂环芳香族基团或其基团可以被一个或多个基团R12取代，或R10选自一个基团R12；R11选自0-、N-、NH-、N═C、CO-、C00-、CON-、CONH-、S02-、S02N-、S02NH-；R12选自卤素、NH2、N02、CN、OH、COOH、CONH2、C(═NH)NH2、S03H、S02NH2、S02CH3、OCH3、OCH2CH3、CF3；R8和R9包括一个或多个独立选择的增溶基团，包括i）中性亲水基团，ii）离子性有机酸，iii）离子性有机碱，iv）提供共价或非共价固定或结合到固相或不动的受体的化学功能或基团以及其组合物；R4、R5和R6各自独立地选自H和R10，或其中的两个被连接成含有一个或多个额外氧原子或氮原子的环醚或胺。该化合物可用于治疗由AKT、Aurora激酶、BCR-ABL、CDK、FLT、GSK3、IKK、JAK、MAPK、PDGF、PI3K、PKA、PKB、PKC、PLK、Src和VEGF家族酶中的一个或多个酶介导的疾病，或用于治疗癌症或其他增殖性疾病，或用于抑制癌细胞的生长，或用于诱导人或动物主体中癌细胞的凋亡。
• Stereochemistry of Base-catalysed Addition of Methyl Mercaptoacetate to Acetylenic Ketones and Esters. Effects of Activating Groups and Solvents
  作者：Mohamed Nabih Basyouni、Mohamed Tawfik Omar、Edwar Amin Ghali

  DOI：10.1246/bcsj.53.1739

  日期：1980.6

  inverted when the latter addition was carried out in dry benzene. Rationalisation of these results is presented which depends on the effect of activating groups and solvents on the stereochemistry of addition. Piperidine-catalysed addition of methyl mercaptoacetate to methyl phenylpropiolate in ethanol gave methyl (Z)-3-(methoxycarbonylmethylthio)cinnamate. Hydrazine hydrate converted some of the above mono-adducts

  哌啶催化巯基乙酸甲酯与乙醇中的苯甲酰基-和对-氯苯甲酰基-苯基乙炔的加成得到相应的(Z)-1-芳基-3-(甲氧羰基甲硫基)-3-苯基-2-丙烯-1-酮。然而，对苯异酰基苯基乙炔以 4:1 的比例得到 (Z)- 和 (E)-3-(甲氧基羰基甲硫基)-1-(对甲氧基苯基)-3-苯基-2-丙烯-1-酮的混合物. 当后者在无水苯中添加时，该比例完全颠倒。这些结果的合理化取决于活化基团和溶剂对加成立体化学的影响。哌啶催化巯基乙酸甲酯与乙醇中的苯丙酸甲酯的加成得到(Z)-3-(甲氧基羰基甲硫基)肉桂酸甲酯。水合肼将一些上述单加合物转化为一些吡唑衍生物。