4,4-dimethyl-1,2,3,4-tetrahydro-1-quinazolinone | 28721-19-9

• 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: 4,4-dimethyl-1,2,3,4-tetrahydro-1-quinazolinone
• 英文别名: 4,4-dimethyl-3,4-dihydro-1H-quinazolin-2-one；4,4-Dimethyl-3,4-dihydroquinazolin-2(1H)-one；4,4-dimethyl-1,3-dihydroquinazolin-2-one
• CAS: 28721-19-9
• 化学式: C₁₀H₁₂N₂O
• mdl: MFCD02661417
• 分子量: 176.218
• InChiKey: QAENFGLSHOAYSC-UHFFFAOYSA-N

物化性质

• 沸点：
  262.5±33.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-1,2,3,4-tetrahydro-1-quinazolinone 在 三氯化铝 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 5-(4,4-Dimethyl-2-oxo-1,3-dihydroquinazolin-6-yl)-6-methyl-3,6-dihydro-1,3,4-thiadiazin-2-one
  参考文献：
  名称：

  一类新型的强心剂：具有环AMP磷酸二酯酶抑制作用和肌原纤维钙敏化特性的5取代3,6-二氢噻二嗪-2-酮的合成和生物学评估。

  摘要：

  作为寻找新的强心剂的重要组成部分，新的强心剂使心肌收缩蛋白对钙显着敏感，同时具有对心脏环AMP-PDE的抑制活性，我们发现新颖的5位取代的3,6-二氢噻二嗪-2-酮可能同时具有这两种特性。通过空间和电子需求来确定收缩蛋白对钙的敏化作用，该作用通过犬心肌肌原纤维镁依赖性ATP酶对钙敏感性的变化来评估。磷酸二酯酶抑制的要求，特别是苯基和噻二嗪-2-一环的近平面排列的要求，与已经描述的类似哒嗪酮的要求是一致的。讨论了合成和构效关系。

  DOI：

  10.1021/jm00079a022
• 作为产物：
  描述：

  ethyl N-(2-(1-benzyloxycarbonylamino-1-methylethyl)phenyl)carbamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4,4-dimethyl-1,2,3,4-tetrahydro-1-quinazolinone
  参考文献：
  名称：

  Study of biscarbamates derived from 2-aminobenzylamines as models for alcohol prodrugs

  摘要：

  Unsubstituted N-arylcarbamate of title compound does not cyclize to the corresponding cyclic urea: with ROH liberation, under mild conditions (40 degrees C). Substitution of the benzylic position by two methyl groups promotes slow cyclisation while N-methylation of the N-aryl carbamate has a more important effect. Relative cyclisation rates are in agreement with barrier heights obtained from ab initio calculations. The calculations also suggest that the highest cyclisation rate of the latter is a consequence of the steric hindrance caused by the N-methyl substituent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00139-8

文献信息

• Iridium(III)-Catalyzed Benzylic Amine Directed CH Sulfonamidation of Arenes with Sulfonyl Azides
  作者：Heng Chen、Malcolm P. Huestis

  DOI：10.1002/cctc.201402944

  日期：2015.3

  The development of a benzylic amine directed ortho‐sulfonamidation of aryl CH bonds with sulfonyl azides was investigated. The combination of a commercially available iridium(III) complex with a silver salt gave rise to an active manifold capable of promoting efficient CN bond formation for a variety of substrates.

  研究了苄基胺指导的磺酰叠氮化物对芳基CH键的邻位磺酰胺化的研究。商业上可获得的铱（III）配合物与银盐的结合产生了一种活性歧管，该活性歧管能够促进各种底物的有效CN键形成。
• New Spirotricyclic Derivatives and Their Use as Phosphodiesterase-7 Inhibitors
  申请人：Bernardelli Patrick

  公开号：US20070049558A1

  公开（公告）日：2007-03-01

  The invention provides compounds which are PDE7 inhibitors, having the following formula (I), (II) and (III) in which X 1 , X 2 , X 3 , X 4 , X, Y, Z, A and Z 1 are as defined in the description, methods for preparing them and their use for the treatment of disorders for which therapy by a PDE7 inhibitor is relevant.

  本发明提供了以下式子(I)、(II)和(III)的PDE7抑制剂化合物，其中X1、X2、X3、X4、X、Y、Z、A和Z1的定义如说明书中所述，以及制备它们的方法和它们用于治疗需要PDE7抑制剂治疗的疾病的用途。
• US7214676B2
  申请人：——

  公开号：US7214676B2

  公开（公告）日：2007-05-08
• A novel class of cardiotonic agents: synthesis and biological evaluation of 5-substituted 3,6-dihydrothiadiazin-2-ones with cyclic AMP phosphodiesterase inhibiting and myofibrillar calcium sensitizing properties
  作者：Marie Claire Forest、Philippe Lahouratate、Michel Martin、Guy Nadler、Marie Josee Quiniou、Richard G. Zimmermann

  DOI：10.1021/jm00079a022

  日期：1992.1

  As part of a search for new cardiotonic agents significantly sensitising the myocardial contractile proteins to calcium, together with cardiac cyclic AMP-PDE inhibitory activity, we have discovered that novel 5-substituted 3,6-dihydrothiadiazin-2-ones may fulfill both properties. The sensitising effect of the contractile proteins to calcium, assessed by the shift in the calcium sensitivity of canine

  作为寻找新的强心剂的重要组成部分，新的强心剂使心肌收缩蛋白对钙显着敏感，同时具有对心脏环AMP-PDE的抑制活性，我们发现新颖的5位取代的3,6-二氢噻二嗪-2-酮可能同时具有这两种特性。通过空间和电子需求来确定收缩蛋白对钙的敏化作用，该作用通过犬心肌肌原纤维镁依赖性ATP酶对钙敏感性的变化来评估。磷酸二酯酶抑制的要求，特别是苯基和噻二嗪-2-一环的近平面排列的要求，与已经描述的类似哒嗪酮的要求是一致的。讨论了合成和构效关系。
• Study of biscarbamates derived from 2-aminobenzylamines as models for alcohol prodrugs
  作者：Sébastien Papot、Christian Bachmann、Damien Combaud、Jean-Pierre Gesson

  DOI：10.1016/s0040-4020(99)00139-8

  日期：1999.4

  Unsubstituted N-arylcarbamate of title compound does not cyclize to the corresponding cyclic urea: with ROH liberation, under mild conditions (40 degrees C). Substitution of the benzylic position by two methyl groups promotes slow cyclisation while N-methylation of the N-aryl carbamate has a more important effect. Relative cyclisation rates are in agreement with barrier heights obtained from ab initio calculations. The calculations also suggest that the highest cyclisation rate of the latter is a consequence of the steric hindrance caused by the N-methyl substituent. (C) 1999 Elsevier Science Ltd. All rights reserved.