N-(2-(methylthio)ethyl)aniline | 80865-94-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-(methylthio)ethyl)aniline
• 英文别名: [beta-(Methylthio)ethyl]aniline；N-(2-methylsulfanylethyl)aniline
• CAS: 80865-94-7
• 化学式: C₉H₁₃NS
• 分子量: 167.275
• InChiKey: RJJIVFLXJQOMCG-UHFFFAOYSA-N

物化性质

• 沸点：
  60-61 °C(Press: 0.001 Torr)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-(methylthio)ethyl)aniline 在 间氯过氧苯甲酸 作用下， 生成 N-(2-methylsulfonylethyl)aniline
  参考文献：
  名称：

  Cardioselective Antiischemic ATP-Sensitive Potassium Channel (K_ATP) Openers. 5. Identification of 4-(N-Aryl)-Substituted Benzopyran Derivatives with High Selectivity

  摘要：

  This paper describes our studies aimed at the discovery of structurally distinct analogs of the cardioprotective K-ATP Opener BMS-180448 (2) with improved selectivity for the ischemic myocardium. The starting compound 6, derived from the indole analog 4, showed good cardioprotective potency and excellent selectivity compared to 2 and the first-generation K-ATP opener cromakalim (1). The structure-activity studies indicate that increasing the size of the alkyl ester leads to diminished potency as does its replacement with a variety of other groups (nitrile, methyl sulfone). Replacement of the ethyl ester of 6 with an imidazole gave the best compound 3 (BMS-191095) of this series which maintains the potency and selectivity of its predecessor 6. The results described in this publication further support that there is no correlation between vasorelaxant and cardioprotective potencies of K-ATP openers. Compound 3 is over 20- and 4000-fold more selective far the ischemic myocardium than 2 and cromakalim (1), respectively. The selectivity for the ischemic myocardium is achieved by reduction of vasorelaxant potency rather than enhancement in antiischemic potency. As for cromakalim (1) and 2, the cardioprotective effects of compound 3 are inhibited by cotreatment with the K-ATP blocker glyburide, indicating that the K-ATP Opening is involved in its mechanism of cardioprotection With its good oral bioavailability (47%) and plasma elimination half life (3 h) in rats, compound 3 offers an excellent candidate to investigate the role of residual vasorelaxant potency of 2 toward its cardioprotective activity in vivo.

  DOI：

  10.1021/jm9605905
• 作为产物：
  描述：

  2-甲硫基乙醇 、 苯胺 在 bis(triphenylphosphine)carbonylmonohydrate ruthenium dichloride 作用下， 反应 5.0h， 以50%的产率得到N-(2-(methylthio)ethyl)aniline
  参考文献：
  名称：

  含硫胺的直接 N-烷基化

  摘要：

  已经开发了一种高效的钌催化方法，用于通过逐步经济和环境友好的氢借用策略直接将含硫胺与醇进行N-烷基化。本方法的特点是无碱条件和广泛的底物范围，水是唯一的副产品。此外，该协议已应用于药物喹硫平的合成。

  DOI：

  10.1039/d1ob00368b

文献信息

• Quinoline-3-carbothioamides and related compounds as novel immunomodulating agents
  作者：Takashi Tojo、Glen W Spears、Kiyoshi Tsuji、Hiroaki Nishimura、Takashi Ogino、Nobuo Seki、Aiko Sugiyama、Masaaki Matsuo

  DOI：10.1016/s0960-894x(02)00377-3

  日期：2002.9

  A series of quinoline-3-carbothioamides and their analogues was prepared via four synthetic routes and evaluated for their antinephritic and immunomodulating activities. The optimal compound 9g strongly inhibited the T-cell independent antibody production in mice immunized with TNP-LPS and was highly effective in two nephritis models, namely chronic graft-versus-host disease and autoimmune MRL/l mice

  通过四种合成途径制备了一系列喹啉-3-碳硫代酰胺及其类似物，并评估了它们的抗肾炎和免疫调节活性。最佳化合物9g在用TNP-LPS免疫的小鼠中强烈抑制了T细胞独立抗体的产生，并且在两种肾炎模型（即慢性移植物抗宿主病和自身免疫MRL / 1小鼠）中非常有效。
• USE OF PHYSIOLOGICAL COOLING ACTIVE INGREDIENTS, AND COMPOSITIONS COMPRISING SUCH ACTIVE INGREDIENTS
  申请人：BASF SE

  公开号：US20200190052A1

  公开（公告）日：2020-06-18

  The invention relates primarily to a method of modulation, preferably of in vitro and/or in vivo modulation, of the cold menthol receptor TRPM8, wherein the receptor is contacted with at least one modulator selected from the group consisting of the compounds of the structure type 1 described herein. The present invention further relates to corresponding uses and compositions comprising such compounds.

  该发明主要涉及一种调制方法，优选是体外和/或体内调制寒冷薄荷醇受体TRPM8的方法，其中受体与本文描述的结构类型1的化合物群中至少一种调制剂接触。本发明还涉及相关用途和包含这些化合物的组合物。
• P-phenylenediamines, process for preparation thereof, dyeing
  申请人：L'Oreal

  公开号：US05032137A1

  公开（公告）日：1991-07-16

  The invention relates to p-phenylenediamines of formula: ##STR1## in which R.sub.1 denotes an alkyl, hydroxyalkyl or polyhydroxyalkyl radical and R.sub.2 denotes a hydrogen atom or an alkyl radical, as well as the corresponding salts with acids, and to the compositions and the process for dyeing keratinous fibres, and especially hair, employing them.

  本发明涉及以下式子的p-苯二胺：##STR1## 其中R.sub.1代表烷基，羟基烷基或多羟基烷基基团，R.sub.2代表氢原子或烷基基团，以及与酸对应的相应盐，以及使用它们染色角质蛋白纤维，特别是头发的组合物和过程。
• THIOALKYLAMINE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：EP1216988A1

  公开（公告）日：2002-06-26

  The present invention relates to a thioalkylamine derivative represented by general formula (I); and a process for production thereof: wherein each of R1 and R2 is H, (C1-C4)alkyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl (C1-C4) alkyl, (substituted) phenyl, (substituted) phenyl(C1-C4) alkyl, or the like; each of R3 and R4 is H or a (C1-C4)alkyl group; each of R5 and R6 is H, (C1-C4)alkyl, a (substituted) phenyl group or a (substituted) phenyl(C1-C4)alkyl group; alternatively each of R1 and R2, R1 and R3 or R5, R3 and R4, R3 and R5, or R5 and R6 may together form lower alkylene; and R is (C1-C12)alkyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl (C1-C4) alkyl, (substituted) phenyl, (substituted) phenyl (C1-C4)alkyl, a naphthyl group, a (substituted) aromatic heterocyclic, or the like.

  本发明涉及通式（I）所代表的硫代烷基胺衍生物及其生产工艺： 其中R1和R2各自为H、(C1-C4)烷基、(C3-C8)环烷基、(C3-C8)环烷基(C1-C4)烷基、(取代)苯基、(取代)苯基(C1-C4)烷基或类似物；R3和R4各自为H或(C1-C4)烷基；R5和R6各自为H、(C1-C4)烷基、(取代)苯基或(取代)苯基(C1-C4)烷基；或者，R1 和 R2、R1 和 R3 或 R5、R3 和 R4、R3 和 R5 或 R5 和 R6 可共同形成低级亚烷基；R 是 (C1-C12)烷基、(C3-C8)环烷基、(C3-C8)环烷基 (C1-C4) 烷基、（取代的）苯基、（取代的）苯基 (C1-C4)烷基、萘基、（取代的）芳香杂环基或类似基团。
• N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1021/jo00090a044

  日期：1994.6

  The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 degrees C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents [H2O, D2O, Me(2)S(2), Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(5)CO, (EtO)(2)CO, CH2=CHCO(2)Me, PhCON(CH2)(4), PhCH=NPh, MeI, and CH2=CHCH2Br] to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5. When the reductive opening and the reaction with electrophiles [H2O, D2O, CH2=CHCH2Br, Me(2)CO, (c-C3H5)(2)CO] were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.