4-(methylthio)isoquinoline | 38896-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-(methylthio)isoquinoline
• 英文别名: 4-methylthioisoquinoline；4-Methylthioisochinolin；4-methylsulfanylisoquinoline
• CAS: 38896-71-8
• 化学式: C₁₀H₉NS
• 分子量: 175.254
• InChiKey: LJJYUBRSIWDHPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  331.2±15.0 °C(Predicted)
• 密度：
  1.18±0.1 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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴异喹啉 、 sodium thiomethoxide 在 sodium amide 作用下， 以 氨 为溶剂， 反应 4.0h， 以80%的产率得到4-(methylthio)isoquinoline
  参考文献：
  名称：

  Nature of the reactions involving 4-haloisoquinolines and amide ion in ammonia. Remarkable competition between SRN1 substitution and .sigma. complex formation

  摘要：

  4-Bromo- (1) or 4-chloroisoquinoline (3) in refluxing liquid ammonia containing amide and thiomethoxide ions reacts preferentially with the thiolate ion to give 4-(methylthio)isoquinoline (2) in high yield. The bromo substrate was shown to require amide ion in order to react with thiomethoxide ion, no reaction taking place in its absence. Substitution product is believed to form from both halides by an S(RN)1 mechanism. By contrast, 3-chloroisoquinoline under the same conditions of mixed anions gives 3-aminoisoquinoline. The role of amide ion and its addition to give sigma complexes in these and other reactions of 4-halogenated isoquinolines in ammonia is discussed.

  DOI：

  10.1021/jo00008a042

文献信息

• Functionalization of pyridine via direct metallation
  作者：Jacob Verbeek、Albert V. E. George、Robertus L. P. de Jong、Lambert Brandsma

  DOI：10.1039/c39840000257

  日期：——

  The isolation of mixtures of 2-, 3-, and 4-deuteriopyridine, 2-, 3-, and 4-trimethylsilylpyridine, or 2-, 3-, and 4-methylthiopyridine indicates successful metallation of pyridine with a 1 : 1 mixture of BuLi-ButOK in tetrahydrofuran–hexane at ––100 °C.

  2-，3-和4-氘代吡啶，2-，3-和4-三甲基甲硅烷基吡啶或2-，3-和4-甲硫基吡啶的混合物的分离表明，吡啶与1：1的混合物成功地金属化在––100°C下于四氢呋喃–己烷中的BuLi-Bu t OK。
• [EN] FUSED RING COMPOUNDS<br/>[FR] COMPOSÉS CYCLIQUES CONDENSÉS
  申请人：GENENTECH INC

  公开号：WO2020035031A1

  公开（公告）日：2020-02-20

  Provided are fused ring compounds of Formula (I), Formula (II), or Formula (III), as further detailed herein, which are used for the inhibition of Ras proteins, as well as compositions comprising these compounds and methods treatment by their administration.

  提供的是公式(I)、公式(II)或公式(III)的融合环化合物，具体细节如下，这些化合物用于抑制Ras蛋白，以及包含这些化合物的组合物和通过其给药的治疗方法。
• Cesium carbonate-promoted synthesis of aryl methyl sulfides using <i>S</i>-methylisothiourea sulfate under transition-metal-free conditions
  作者：Caiyang Zhang、You Zhou、Jintao Huang、Canhui Tu、Xiaoai Zhou、Guodong Yin

  DOI：10.1039/c8ob01758a

  日期：——

  cyclopropylmethylthio groups can be easily introduced into the aromatic rings from the corresponding S-[2-(dimethylamino)ethyl]isothiourea dihydrochloride and S-cyclopropylmethylisothiourea hydrobromide. The possible reaction mechanism is proposed. It is believed that this route to aryl alkyl sulfides is well competitive with currently known methods due to its wide substrate scope, excellent yields, easy

  在碳酸铯的存在下，开发了通过芳基卤化物与可商购的S-甲基异硫脲硫酸盐反应的有效合成芳基甲基硫醚的方法。这种无味且高度结晶的固体可用作恶臭甲硫醇的替代品。在不使用柱色谱分离的情况下，克级反应也可以顺利进行。类似地，2-（二甲基氨基）乙硫基和环丙基甲硫基可容易地从相应的S- [2-（二甲氨基）乙基]异硫脲二盐酸盐和S中引入芳环。-环丙基甲基异硫脲氢溴酸盐。提出了可能的反应机理。据信，由于其广泛的底物范围，优异的收率，易于操作和无过渡金属的条件，该制备芳基烷基硫化物的方法与目前已知的方法具有很好的竞争性。
• PHOSPHATIDYLINOSITOL 3-KINASE INHIBITORS
  申请人：Gilead Sciences, Inc.

  公开号：US20180086719A1

  公开（公告）日：2018-03-29

  The present application provides the compounds of formula I or pharmaceutically acceptable salts, isomers, tautomer, or a mixture thereof, wherein t, R 1 , R 2 , R 3 , R 4 , and R 6 are as described herein.

  本申请提供了式I的化合物或其药学上可接受的盐、异构体、互变异构体或其混合物，其中t、R1、R2、R3、R4和R6如此处所述。
• Effective Formation of New C(sp ² )−S Bonds via Photoactivation of Alkylamine‐based Electron Donor‐Acceptor Complexes
  作者：Jorge C. Herrera‐Luna、María Carmen Pérez‐Aguilar、Leon Gerken、Olga García Mancheño、M. Consuelo Jiménez、Raúl Pérez‐Ruiz

  DOI：10.1002/chem.202203353

  日期：2023.1.27

  An effective approach for the direct thiolation of five-membered heteroarenes involving visible-light-absorbing EDA complexes is reported. The reaction takes place from an EDA complex between an alkylamine and the heteroarene halide. Selective photolysis to the EDA complex has allowed to generate the heteroarene radical that is suitably trapped by disulfide derivatives, providing a potent synthetic

  报道了一种涉及可见光吸收 EDA 配合物的五元杂芳烃直接硫醇化的有效方法。该反应发生在烷基胺和杂芳烃卤化物之间的 EDA 络合物中。对 EDA 复合物的选择性光解可以产生被二硫化物衍生物适当捕获的杂芳烃自由基，提供强大的合成多功能性。