5-Bromo-1-methyl-1,3-dihydro-indole-2-thione | 110994-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-Bromo-1-methyl-1,3-dihydro-indole-2-thione
• 英文别名: 5-bromo-1-methyl-3H-indole-2-thione
• CAS: 110994-26-8
• 化学式: C₉H₈BrNS
• 分子量: 242.139
• InChiKey: JNXVOHHCCLSGRL-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  320.9±52.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Bromo-1-methyl-1,3-dihydro-indole-2-thione 在 air 、 sodium hydride 作用下， 以 甲醇 为溶剂， 生成 2,2'-dithiobis [N-phenyl-5-bromo-1-methylindolyl-3-carboxamide]
  参考文献：
  名称：

  Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

  摘要：

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.

  DOI：

  10.1021/jm00039a016
• 作为产物：
  描述：

  5-溴-1-甲基-2-氧吲哚烷 在 tetraphosphorus decasulfide 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 5-Bromo-1-methyl-1,3-dihydro-indole-2-thione
  参考文献：
  名称：

  AlCl3介导的二氢吲哚-2-硫酮与酰基环丙烷、双环丙烷和螺环环丙烷的开环反应

  摘要：

  研究了AlCl 3介导的二氢吲哚-2-硫酮与各种酰基环丙烷、双环丙烷和螺环环丙烷的亲核开环反应。合成了一系列用吲哚硫基官能化的酮，产率从中等到良好。此外，将4-吲哚硫基丁-1-酮化学转化为二氢-2H-噻吩并[2,3- b ]吲哚和砜，以进一步扩大合成实用性和结构复杂性。

  DOI：

  10.1039/d3ob00909b

文献信息

• Enantioselective synthesis of indolo[2,3-b]-dihydrothiopyranones via [3+3] cycloaddition of chiral α,β-unsaturated acylammonium salts
  作者：Jing-Hai Jin、Xiang-Yu Li、Xiaoyan Luo、Wei-Ping Deng

  DOI：10.1016/j.tet.2018.09.024

  日期：2018.11

  nucleophile-catalyzed Michael addition/proton transfer/lactonization (NCMPL) organocascade process of chiral α,β-unsaturated acylammonium salts and indoline-2-thiones is described, which delivers the indolo[2,3-b]dihydrothiopyranone motifs in high yields (up to 97%) with good to excellent enantioselectivities (up to 98% ee).

  描述了亲核催化剂催化的手性α，β-不饱和酰基铵盐和二氢吲哚-2-硫酮的迈克尔加成/质子转移/内酯化（NCMPL）有机级联反应，该反应可高产率地产生吲哚[2,3- b ]二氢噻喃酮基序（高达97％）具有良好至优异的对映选择性（高达98％ee）。
• Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides
  作者：Shiping Zhou、Genhua Xiao、Yun Liang

  DOI：10.1016/j.tetlet.2016.12.028

  日期：2017.1

  A novel and efficient method for synthesis of 2-sulfenylindole via copper-catalyzed coupling reaction of indoline-2-thiones with aryl iodides has been developed. A series of N-substituted and N-free 2-sulfenylindole were obtained in high yields. Furthermore, the method was employed to synthesis of benzothieno[2,3-b]indoles from indoline-2-thiones with 1,2-diiodobenzene in the presence of CuI and Pd(OAc)2

  通过铜催化的吲哚-2-硫酮与芳基碘的偶联反应合成2-亚磺酰基吲哚的新方法已经得到了发展。以高收率获得了一系列的N-取代的和不含N的2-亚磺酰基吲哚。此外，该方法用于在CuI和Pd（OAc）2作为催化剂存在下，由吲哚啉-2-硫酮与1,2-二碘代苯合成苯并噻吩并[2,3- b ]吲哚。
• Organocatalyzed enantioselective [3 + 3] annulation for the direct synthesis of conformationally constrained cyclic tryptophan derivatives
  作者：L.-L. Wu、Y. Zheng、Y.-M. Wang、Z.-H. Zhou

  DOI：10.1039/c5ra24288f

  日期：——

  + 3] annulation of 1-methylindoline-2-thiones and 4-arylmethylideneoxazolin-5(4H)-ones has been developed by the use of an L-tert-leucine-derived bifunctional tertiary amine-squaramide catalyst, which furnished a series of optically active conformationally strained β-branched cyclic tryptophan derivatives in acceptable yields with good to excellent diastereo- and enantioselectivities.

  对映体选择性正式[3 + 3]的1-甲基吲哚啉-2-硫酮环和4- arylmethylideneoxazolin-5（4 ħ） -酮已经开发通过使用的大号-叔-亮氨酸衍生的双官能叔胺催化剂squaramide ，以可接受的收率提供了一系列旋光性构象应变的β-支化环状色氨酸衍生物，具有良好至优异的非对映选择性和对映选择性。
• 一种手性吲哚并噻喃化合物的合成方法
  申请人：苏州大学

  公开号：CN104497007B

  公开（公告）日：2017-01-18

  本发明公开了一种手性吲哚并噻喃类化合物的合成方法，具体为以硫代吲哚酮与苯甲醛丙二腈为反应物，在手性多功能1R,2R‑二苯基乙二胺硫脲催化剂催化下，在溶剂中合成得到产物。本发明公开的方法原料简单易得，反应条件温和，后处理简单方便，适用的底物范围广，收率高，对映选择性高；由此合成得到的产物可用以合成药物和杀虫剂的中间体。
• Access to Substituted Dihydrothiopyrano[2,3-<i>b</i>]indoles via Sequential Rearrangements During <i>S</i>-Alkylation and Au-Catalyzed Hydroarylation on Indoline-2-thiones
  作者：Mukund Jha、Ganesh M. Shelke、T. Stanley Cameron、Anil Kumar

  DOI：10.1021/jo5025943

  日期：2015.5.15

  the synthesis of indole-fused dihydrothiopyrans has been developed from indoline-2-thiones. The protocol involves the synthesis of conjugated ene-yne-substituted indole-sulfides, a gold(III)-catalyzed rearrangement of the ene-yne side chain followed by intramolecular hydroarylation via C3–H functionalization of the indole core. This new synthesis of functionalized tricyclic indole derivatives through

  从二氢吲哚-2-硫酮开发了一种有效的合成吲哚稠合的二氢硫吡喃的方法。该协议涉及共轭烯-炔取代的吲哚硫化物的合成，金（III）催化的烯-炔侧链的重排，然后通过吲哚核的C3-H官能化进行分子内氢化。通过顺序重排的功能化三环吲哚衍生物的这种新合成本质上是相当普遍的