methyl 4-(ethylthio)benzoate | 99186-27-3

• 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 4-(ethylthio)benzoate
• 英文别名: Methyl 4-(ethylsulfanyl)benzoate；methyl 4-ethylsulfanylbenzoate
• CAS: 99186-27-3
• 化学式: C₁₀H₁₂O₂S
• mdl: MFCD06204272
• 分子量: 196.27
• InChiKey: QQNNYYJRKJMQRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 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：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(ethylthio)benzoate 在 五氧化二钒 、 双氧水 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以80%的产率得到methyl 4-(ethylsulfinyl)benzoate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of potent, selective and orally active anthranilamide-based factor Xa inhibitors: Application of weakly basic sulfoximine group as novel S4 binding element

  摘要：

  A novel series of potent and efficacious factor Xa inhibitors which possesses sulfoximine moiety as novel S4 binding element in anthranilamide chemotype has been identified. Lead optimization at this novel P4 group led to many potent factor Xa inhibitors with excellent anticoagulant activity in human plasma. Selected compounds were dosed orally in rats and checked for their ex vivo prothrombin time prolonging activity, which resulted in identification of compound 5-chloro-N-(5-chloropyridin-2-yl)-2-(4-(N-(2(diethylamino)acetyl)-S-methylsulfonimidoyl)benzamido)benzamide (18f). The detailed pharmacokinetic evaluation and subsequent metabolism study of 181 suggested the presence of an active metabolite. The compound 18f and its active metabolite 18b demonstrated excellent in vivo efficacy in both arterial and venous thrombosis model in rats and were found to be highly selective against related serine proteases. Based on this promising profile, compound 18f was selected for further evaluation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.005
• 作为产物：
  描述：

  methyl 4-((3-methoxy-3-oxopropyl)thio)benzoate 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 13.0h， 生成 methyl 4-(ethylthio)benzoate
  参考文献：
  名称：

  [EN] TGONOVEL HDAC INHIBITORS AND THERAPEUTIC USE THEREOF
  [FR] NOUVEAUX INHIBITEURS DE HDAC ET LEUR UTILISATION THÉRAPEUTIQUE

  摘要：

  Described herein are novel compounds, compositions and methods for treatment of diseases including cancer using such compounds, compositions, and methods. The compounds include those of Formula (I):

  公开号：

  WO2023102162A1

文献信息

• The metalation of thioanisole and thiophenetole with n-butyllithium
  作者：David A. Shirley、Billy J. Reeves

  DOI：10.1016/s0022-328x(00)81629-0

  日期：1969.1

  The metalation of thioanisole and thiophenetole with n-butyllithium in ether has been reinvestigated with careful product analysis. Thioanisole metalates initially in the ring with shift of lithium to the methyl group, probably by transmetalation, although the possibility of concurrent initial attack of the methyl group by n-butyllithium was not excluded by the data.

  用仔细的产物分析重新研究了硫代苯甲醚和噻吩并噻吩与正丁基锂在乙醚中的金属化作用。硫代苯甲醚最初会在环中金属化，可能是通过金属转移而使锂转变为甲基，尽管该数据并未排除甲基同时被正丁基锂初始攻击的可能性。
• A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
  作者：M. L. Czyz、G. K. Weragoda、R. Monaghan、T. U. Connell、M. Brzozowski、A. D. Scully、J. Burton、D. W. Lupton、A. Polyzos

  DOI：10.1039/c8ob00238j

  日期：——

  The general catalytic synthesis of aryl and vinyl thioethers from readily available halides remains a challenge. Herein we report a unified method for the thiolation of aryl and vinyl iodides with dialkyl disulfides using visible light photoredox catalysis. A range of thioether products bearing diverse functional groups can be accessed in high yield and with excellent chemoselectivity. We demonstrate

  由容易获得的卤化物进行的芳基和乙烯基硫醚的一般催化合成仍然是一个挑战。本文中，我们报告了使用可见光光氧化还原催化用二烷基二硫化物对芳基和乙烯基碘进行硫醇化的统一方法。可以以高收率和优异的化学选择性获得一系列带有不同官能团的硫醚产品。我们通过一系列富含硫醚的天然产物的便捷合成证明了该方法的多功能性。从稳态和时间分辨的发光猝灭以及瞬态吸收光谱实验，对光催化机理进行了详细的研究。
• 5-(M-CYANOBENZYLAMINO)PYRAZOLE DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP1304325A1

  公开（公告）日：2003-04-23

  Provided is a 5-(m-cyanobenzylamino)pyrazole derivative represented by the following formula:    wherein: R1 represents a C1-6 alkyl group, a C3-7 cycloalkyl group or a phenyl group; R2 represents a hydrogen atom or a C1-6 alkyl group; R3 represents a C1-6 alkyl, etc., R4 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, etc., Y represents a C1-6 alkyl group, etc.; and n is an integer of 0 to 4; or a salt thereof.

  本发明提供了由下式表示的 5-(间氰基苄基氨基)吡唑衍生物： 其中 R1代表C1-6烷基、C3-7环烷基或苯基； R2代表氢原子或C1-6烷基 R3 代表 C1-6 烷基等、 R4 代表氢原子、卤素原子、C1-6 烷基等、 Y 代表 C1-6 烷基等；以及 n 是 0 至 4 的整数； 或其盐。
• Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates
  作者：Jun-Chen Kang、Zi-Hao Li、Chao Chen、Li-Kun Dong、Shu-Yu Zhang

  DOI：10.1021/acs.joc.1c01891

  日期：2021.11.5
• Synthesis and structure–activity relationship of potent, selective and orally active anthranilamide-based factor Xa inhibitors: Application of weakly basic sulfoximine group as novel S4 binding element
  作者：Vrajesh Pandya、Mukul Jain、Ganes Chakrabarti、Hitesh Soni、Bhavesh Parmar、Balaji Chaugule、Jigar Patel、Tushar Jarag、Jignesh Joshi、Nirav Joshi、Akshyaya Rath、Vishal Unadkat、Bhavesh Sharma、Haresh Ajani、Jeevan Kumar、Kalapatapu V.V.M. Sairam、Harilal Patel、Pankaj Patel

  DOI：10.1016/j.ejmech.2012.10.005

  日期：2012.12

  A novel series of potent and efficacious factor Xa inhibitors which possesses sulfoximine moiety as novel S4 binding element in anthranilamide chemotype has been identified. Lead optimization at this novel P4 group led to many potent factor Xa inhibitors with excellent anticoagulant activity in human plasma. Selected compounds were dosed orally in rats and checked for their ex vivo prothrombin time prolonging activity, which resulted in identification of compound 5-chloro-N-(5-chloropyridin-2-yl)-2-(4-(N-(2(diethylamino)acetyl)-S-methylsulfonimidoyl)benzamido)benzamide (18f). The detailed pharmacokinetic evaluation and subsequent metabolism study of 181 suggested the presence of an active metabolite. The compound 18f and its active metabolite 18b demonstrated excellent in vivo efficacy in both arterial and venous thrombosis model in rats and were found to be highly selective against related serine proteases. Based on this promising profile, compound 18f was selected for further evaluation. (C) 2012 Elsevier Masson SAS. All rights reserved.