4-(2-methoxyphenyl)-7,7-dimethyl-2-thioxo-1,2,3,4,7,8-hexahydroquinazolin-5(6H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(2-methoxyphenyl)-7,7-dimethyl-2-thioxo-1,2,3,4,7,8-hexahydroquinazolin-5(6H)-one
• 英文别名: 4-(2-methoxyphenyl)-7,7-dimethyl-2-sulfanylidene-3,4,6,8-tetrahydro-1H-quinazolin-5-one
• 化学式: C₁₇H₂₀N₂O₂S
• 分子量: 316.424
• InChiKey: RHKOURQYSNZCGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-methoxyphenyl)-7,7-dimethyl-2-thioxo-1,2,3,4,7,8-hexahydroquinazolin-5(6H)-one 在 sodium azide 、 mercury(II) diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以70%的产率得到9-(2-methoxyphenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one
  参考文献：
  名称：

  One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide

  摘要：

  An novel, versatile and cost-effective approach for tetrazolo[1,5-a]pyrimidines and tetrazolo[1,5-a]quinazolines from cyclization reaction of dihydropyrimidinethiones with sodium azide in the presence of mercuric acetate is described. To compare this procedure with the conventional method, we carried out the cyclization reactions through direct functionalization of the pyrimidinethione core, which obtained from Biginelli 3,4-dihydropyrimidine-2-thiones or 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones.

  DOI：

  10.3987/com-11-12351
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 硫脲 、 邻甲氧基苯甲醛 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-(2-methoxyphenyl)-7,7-dimethyl-2-thioxo-1,2,3,4,7,8-hexahydroquinazolin-5(6H)-one
  参考文献：
  名称：

  KF/Al₂O₃ Promoted Aza-Michael Addition of 4-Aryl-7,7-Dimethyloctahydro-Quinazolinones to α, β-Ethylenic Compounds

  摘要：

  在 KF/Al2O3 的存在下，4-芳基-7,7-二甲基-1,2,3,4,5,6,7,8-八氢喹唑啉-2-酮/硫酮-5-酮与α,β-乙烯基化合物发生偶氮-迈克尔加成反应，生成 N3 取代的喹唑啉酮衍生物。喹唑啉酮苯环 o 位上的那些立体阻碍较大的基团（NO2、MeO）对化学选择性有明显的影响，从而产生 N1 取代的产物。

  DOI：

  10.3184/174751911x13129294387591

文献信息

• Synthesis of novel thiazolo[2,3-<i>b</i>]quinazolines by cyclization reaction of octahydroquinazoline-2-thiones with <i>α-</i>bromoketones
  作者：Zheng-Jun Quan、Ying Wei、Xi-Cun Wang

  DOI：10.1515/hc.2011.041

  日期：2011.12.1

  Abstract Novel thiazolo[2,3-b]quinazolines were prepared by the cyclization reaction between octahydroquinazoline-2-thiones with α-bromoketones, which provides a readily accessible multifunctionalized quinazoline template for diversity-oriented synthesis.

  摘要 通过八氢喹唑啉-2-硫酮与α-溴酮之间的环化反应制备了新型噻唑并[2,3-b]喹唑啉，为面向多样性的合成提供了一种易于获得的多功能喹唑啉模板。
• Yarim, Mine; Sarac, Selma; Ertan, Mevluet, Arzneimittel-Forschung/Drug Research, 2002, vol. 52, # 1, p. 27 - 33
  作者：Yarim, Mine、Sarac, Selma、Ertan, Mevluet、Kilic, F. Sultan、Erol, Kevser

  DOI：——

  日期：——
• One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide
  作者：Xi-Cun Wang、Ying Wei、Yu-Xia Da、Zhang Zhang、Zheng-Jun Quan

  DOI：10.3987/com-11-12351

  日期：——

  An novel, versatile and cost-effective approach for tetrazolo[1,5-a]pyrimidines and tetrazolo[1,5-a]quinazolines from cyclization reaction of dihydropyrimidinethiones with sodium azide in the presence of mercuric acetate is described. To compare this procedure with the conventional method, we carried out the cyclization reactions through direct functionalization of the pyrimidinethione core, which obtained from Biginelli 3,4-dihydropyrimidine-2-thiones or 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones.
• KF/Al₂O₃ Promoted Aza-Michael Addition of 4-Aryl-7,7-Dimethyloctahydro-Quinazolinones to α, β-Ethylenic Compounds
  作者：Xi-Cun Wang、Zhong-Jie Wang、Zhang Zhang、Zheng-Jun Quan

  DOI：10.3184/174751911x13129294387591

  日期：2011.8

  The aza-Michael addition reaction of 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-one/thione-5-ones to α,β-ethylenic compounds in the presence of KF/Al₂O₃ furnishes N3-substituted quinazolinone derivatives. Those groups (NO₂, MeO) with larger steric hindrance at the o-position of the phenyl ring of quinazolinone have an apparent affect on the chemical selectivity thus giving the N1-subsituted products.

  在 KF/Al2O3 的存在下，4-芳基-7,7-二甲基-1,2,3,4,5,6,7,8-八氢喹唑啉-2-酮/硫酮-5-酮与α,β-乙烯基化合物发生偶氮-迈克尔加成反应，生成 N3 取代的喹唑啉酮衍生物。喹唑啉酮苯环 o 位上的那些立体阻碍较大的基团（NO2、MeO）对化学选择性有明显的影响，从而产生 N1 取代的产物。