4-phenylthioisoquinoline | 20146-26-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-phenylthioisoquinoline
• 英文别名: 4-(phenylthio)quinoline；4-phenylsulfanyl-quinoline；4-Phenylmercapto-chinolin；4-Phenylthiochinolin；4-(Phenylsulfanyl)quinoline；4-phenylsulfanylquinoline
• CAS: 20146-26-3
• 化学式: C₁₅H₁₁NS
• 分子量: 237.325
• InChiKey: CACIVVUUNUBEIY-UHFFFAOYSA-N

物化性质

• 熔点：
  84.0-85.5 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  214-221 °C(Press: 8 Torr)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenylthioisoquinoline 生成 二苯二硫醚
  参考文献：
  名称：

  FRANCISCO, MANUEL A.;KURS, ARGO;KATRITZKY, ALAN R.;RASALA, DANUTA, J. ORG. CHEM., 53,(1988) N 20, C. 4821-4826

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(phenylthio)quinoline 1-oxide 在 三苯基膦 作用下， 反应 2.0h， 以69%的产率得到4-phenylthioisoquinoline
  参考文献：
  名称：

  Conformational effects in the alkali-metal reduction of diaryl sulfides. 2. Evidence for episulfide intermediates

  摘要：

  DOI：

  10.1021/jo00255a030

文献信息

• Nucleophile and aryl radical reactivity in SRN1 aromatic nucleophilic substitution reactions. Absolute and relative electrochemical determination
  作者：Christian Amatore、Mehmet A. Oturan、Jean Pinson、Jean Michel Saveant、Andre Thiebault

  DOI：10.1021/ja00298a009

  日期：1985.6

  Utilisation de 3 methodes electrochimiques pour determiner les reactivites d'une serie de 26 couples radical aryl-nucleophile

  利用 3 种方法电致化学反应倾析反应性 d'une serie de 26 对自由基芳基亲核试剂
• Efficient nucleophilic substitution reactions of quinolyl and isoquinolyl halides with nucleophiles under focused microwave irradiation
  作者：Yie-Jia Cherng

  DOI：10.1016/s0040-4020(01)01225-x

  日期：2002.2

  Nucleophilic substitution reactions of 2-chloroquinoline, 3-bromoquinoline and 4-bromoisoquinoline with thiolate, alkoxy ions and aniline were completed within several minutes under microwave irradiation. This method gives the desired products with yields up to 99% in a short reaction time, and is superior to the classical heating process.

  在微波辐射下，在几分钟内完成了2-氯喹啉，3-溴喹啉和4-溴异喹啉与硫醇盐，烷氧基离子和苯胺的亲核取代反应。该方法在较短的反应时间内可提供所需的产物，收率高达99％，并且优于传统的加热工艺。
• Studies in the Cyanine Dye Series. XI.¹ The Merocyanines
  作者：L. G. S. Brooker、G. H. Keyes、R. H. Sprague、R. H. VanDyke、E. VanLare、G. VanZandt、F. L. White

  DOI：10.1021/ja01155a095

  日期：1951.11
• Synthesis and reactivity of lithium tri(quinolinyl)magnesates
  作者：Sylvain Dumouchel、Florence Mongin、François Trécourt、Guy Quéguiner

  DOI：10.1016/j.tet.2003.06.001

  日期：2003.10

  2-, 3- and 4-Bromoquinolines, were converted to the corresponding lithium tri(quinolinyl)magnesates at -10degreesC when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines. (C) 2003 Elsevier Ltd. All rights reserved.
• Complex base-induced generation of 3,4-dehydroquinoline: a new access to quinoline derivatives
  作者：Stéphanie Blanchard、Gérald Guillaumet、Paul Caubère

  DOI：10.1016/s0040-4039(01)01339-9

  日期：2001.10

  3,4-Dehydroquinoline was easily generated from 3-bromoquinoline and a complex base NaNH2-tBuONa. Nucleophilic condensation of amines and thiolates were performed in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.