8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione | 65331-29-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione
• 英文别名: 8-(4-methylbenzylidene)-4-(4-methylphenyl)-3,4,5,6,7,8-hexahydro-1H-quinazolin-2-thione；4-(4-Methylphenyl)-8-[(4-methylphenyl)methylidene]-1,3,4,5,6,7-hexahydroquinazoline-2-thione
• CAS: 65331-29-5
• 化学式: C₂₃H₂₄N₂S
• 分子量: 360.523
• InChiKey: IJILAXXAWSYFLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229 °C(Solv: ethanol (64-17-5); ethyl acetate (141-78-6))
• 沸点：
  541.7±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到4a,8a-trans-8-(4-methylbenzylidene)-4-(4-methylphenyl)octahydroquinazoline-2(1H)-thione
  参考文献：
  名称：

  trans-Stereoselective Reduction of Hexahydroquinazoline-2(1H)-thione Derivatives

  摘要：

  Reduction of substituted 4-arylhexahydroquinazoline-2(1H)-thiones using NaBH4/CF3CO2H in chloroform gave the corresponding trans-fused octahydroquinazoline-2(1H)-thiones. The use of two reducing systems, NaBH4/CH3CO2H or NaBH4/CF3CO2H, permitted the consecutive trans-selective reduction of the endo- and exocyclic double bond in the case of 8-dithiomethylidene derivatives of hexahydroquinazoline-2(1H)-thiones.

  DOI：

  10.1007/s10593-013-1247-8
• 作为产物：
  描述：

  环己酮 、 对甲基苯甲醛 、 硫脲 在 bis(tetrabutylammonium) hexatungstate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.2h， 以86%的产率得到8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione
  参考文献：
  名称：

  一种使用四丁基六钨酸铵作为可重复使用的多相化合物合成一些新型 8-亚苄基-4-苯基-3,4,5,6,7,8-六氢-1H-喹唑啉-2-酮/硫酮的高效且环保的方法无溶剂条件下的催化剂

  摘要：

  芳香醛与环己酮与脲或硫脲反应制备8-亚苄基-4-苯基-3,4,5,6,7,8-六氢-1H-喹唑啉-2酮/硫酮的有效方法已经开发出在热和无溶剂条件下存在四丁基六钨酸铵 [TBA]2[W6O19] 作为一种高效、廉价的催化剂。产率高、反应时间短、后处理简单、催化剂的可重复使用性和绿色条件是该过程最明显的优势。

  DOI：

  10.5012/bkcs.2013.34.11.3289

文献信息

• Direct Synthesis of Trichloro-thiazolo[3,2-<i>a</i>]pyrimidine and Thiazolo[2,3-<i>b</i>]quinazoline Derivatives
  作者：Ali Darehkordi、Seyed Mahdi Fazli-Zafarani、Mansoureh Kamali

  DOI：10.1002/jhet.2816

  日期：2017.7

  An efficient one‐pot method for synthesis of new biologically active thiazolo[3,2‐a]pyrimidine and thiazolo[2,3‐b]quinazoline derivatives is described via reaction of pentachloropyridine with fused pyrimidine‐2(5H)‐thiones or quinazoline‐2(1H)‐thiones. These reactions were carried out in the presence of potassium carbonate as a base in acetonitrile as a solvent to produce products 3a–n in good‐to‐excellent

  通过五氯吡啶与稠合的嘧啶-2（5 H）-硫酮的反应，描述了一种有效的一锅法合成新的生物活性噻唑并[3,2- a ]嘧啶和噻唑并[2,3- b ]喹唑啉衍生物。喹唑啉-2（1 H）-硫酮。这些反应是在乙腈作为溶剂的碳酸钾作为碱存在下进行的，从而以良好至优异的产率生产出3a - n产物。五氯吡啶是形成环环状噻唑并[3,2- a ]嘧啶和噻唑并[2,3- b ]喹唑啉产物的双重亲电基石。
• An Efficient and Environmentally Friendly Procedure for the Synthesis of Some Novel 8-Benzylidene-4-phenyl-3,4,5,6,7,8-hexahydro-1H-quinazolin-2-ones/thiones using Tetrabutylammonium Hexatungstate as a Reusable Heterogeneous Catalyst under Solvent-Free Conditions
  作者：Majid Ghashang、Syed Sheik Mansoor、Krishnamoorthy Aswin

  DOI：10.5012/bkcs.2013.34.11.3289

  日期：2013.11.20

  An efficient method for the preparation of 8-benzylidene-4-phenyl-3,4,5,6,7,8-hexahydro-1H-quinazolin-2ones/thiones from the reaction of aromatic aldehydes with cyclohexanone and urea or thiourea in the presence of Tetrabutylammonium hexatungstate, [TBA]2[W6O19], as an efficient, inexpensive catalyst under thermal and solvent-free conditions has been developed. Good yields, short reaction times, straightforward

  芳香醛与环己酮与脲或硫脲反应制备8-亚苄基-4-苯基-3,4,5,6,7,8-六氢-1H-喹唑啉-2酮/硫酮的有效方法已经开发出在热和无溶剂条件下存在四丁基六钨酸铵 [TBA]2[W6O19] 作为一种高效、廉价的催化剂。产率高、反应时间短、后处理简单、催化剂的可重复使用性和绿色条件是该过程最明显的优势。
• trans-Stereoselective Reduction of Hexahydroquinazoline-2(1H)-thione Derivatives
  作者：I. M. Gella、O. D. Bui、A. V. Mirnyi、S. V. Shishkina、O. V. Shishkin、V. D. Orlov

  DOI：10.1007/s10593-013-1247-8

  日期：2013.5

  Reduction of substituted 4-arylhexahydroquinazoline-2(1H)-thiones using NaBH4/CF3CO2H in chloroform gave the corresponding trans-fused octahydroquinazoline-2(1H)-thiones. The use of two reducing systems, NaBH4/CH3CO2H or NaBH4/CF3CO2H, permitted the consecutive trans-selective reduction of the endo- and exocyclic double bond in the case of 8-dithiomethylidene derivatives of hexahydroquinazoline-2(1H)-thiones.