5-[(Z)-(2-methyl-1H-indol-3-yl)methylidene]-3-(4-methylphenyl)-2-thioxoimidazolidin-4-one | 317384-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-[(Z)-(2-methyl-1H-indol-3-yl)methylidene]-3-(4-methylphenyl)-2-thioxoimidazolidin-4-one
• 英文别名: (Z)-3'-deimino-2',4'-bis(demethyl)-4'-(4-methylphenyl)-2-methyl-3'-thioxoaplysinopsin；5-[(2-methylindol-3-yl)methylidene]-3-(4-methylphenyl)-2-thioxoimidazolidin-4-one；(Z)-5-[(2-methyl-1H-indol-3-yl)methylidene]-3-(4-methylphenyl)-2-thioxoimidazolidin-4-one；(5Z)-5-[(2-methyl-1H-indol-3-yl)methylidene]-3-(4-methylphenyl)-2-sulfanylideneimidazolidin-4-one
• CAS: 317384-13-7
• 化学式: C₂₀H₁₇N₃OS
• 分子量: 347.44
• InChiKey: REIKQCFBXKMDAC-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.13
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-[(Z)-(2-methyl-1H-indol-3-yl)methylidene]-3-(4-methylphenyl)-2-thioxoimidazolidin-4-one 、 苯甲酰氯 4-氯苯基腙 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以85%的产率得到2-(4-chlorophenyl)-8-[(Z)-1-(2-methyl-1H-indol-3-yl)methylidene]-4-phenyl-6-(4-methylphenyl)-1-thia-3,4,6,9-tetraaza-spiro[4.4]non-2-en-7-one
  参考文献：
  名称：

  Synthesis of Thioaplysinopsin Analogs Derived from 5-Dimethylaminomethylidene-2-thioxo-1,3-thiazol-4-ones

  摘要：

  DOI：

  10.3987/com-07-s(u)55
• 作为产物：
  描述：

  methyl 2-{[2,2-bis(acetyl)ethenyl]amino}-3-(2-methyl-1H-indol-3-yl)prop-2-enoate 在 一水合肼 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 3.83h， 生成 5-[(Z)-(2-methyl-1H-indol-3-yl)methylidene]-3-(4-methylphenyl)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  摘要：

  Simple and stereoselective syntheses of aplysinopsins and their analogs from either methyl 2-[(2,2 disubstituted ethenyl)amino]-3-(dimethylamino)prop-2-enoates or 5-[(dimethylamino)methylidene]imidazolidine-2,4-diones 20 are described. The structures of products are established by H-1 and C-13-NMR. and NOESY spectroscopy, and X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(20001004)83:10<2802::aid-hlca2802>3.0.co;2-9

文献信息

• A simple synthesis of aplysinopsin analogues by dimethylamine substitution in N,N-(dimethylamino)methylidene derivatives of five-membered heterocycles
  作者：Renata Jakše、Simon Rečnik、Jurij Svete、Amalija Golobič、Ljubo Golič、Branko Stanovnik

  DOI：10.1016/s0040-4020(01)00838-9

  日期：2001.9

  Some new aplysinopsin analogues were prepared by a simple coupling of N,N-(dimethylamino)methylidene substituted hydantoin, thiohydantoin, and thiazolone derivatives, with indole derivatives. Configuration around the exocyclic CC double bond was determined on the basis of long-range heteronuclear coupling constants using 2D HMBC correlation technique.

  通过将N，N-（二甲基氨基）亚甲基取代的乙内酰脲，硫代乙内酰脲和噻唑酮衍生物与吲哚衍生物简单偶联，制备了一些新的皂素类似物。基于远距离异核偶联常数，使用2D HMBC相关技术确定了环外CC双键周围的构型。
• ——
  作者：Lovro Selič、Renata Jakše、Kristina Lampič、Ljubo Golič、Simona Golič-Grdadolnik、Branko Stanovnik

  DOI：10.1002/1522-2675(20001004)83:10<2802::aid-hlca2802>3.0.co;2-9

  日期：2000.10.4

  Simple and stereoselective syntheses of aplysinopsins and their analogs from either methyl 2-[(2,2 disubstituted ethenyl)amino]-3-(dimethylamino)prop-2-enoates or 5-[(dimethylamino)methylidene]imidazolidine-2,4-diones 20 are described. The structures of products are established by H-1 and C-13-NMR. and NOESY spectroscopy, and X-ray crystal-structure analysis.
• Synthesis of Thioaplysinopsin Analogs Derived from 5-Dimethylaminomethylidene-2-thioxo-1,3-thiazol-4-ones
  作者：Branko Stanovnik、Renata Jakse、Uros Groselj、Gorazd Sorsak、Jurij Svete

  DOI：10.3987/com-07-s(u)55

  日期：——