2-phenyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-ol | 5719-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-phenyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-ol
• 英文别名: 2-phenyl-5,7-dihydro-3H-thieno[3,4-d]pyrimidin-4-one；2-Phenyl-5,7-dihydrothieno[3,4-D]pyrimidin-4-OL；2-phenyl-5,7-dihydro-3H-thieno[3,4-d]pyrimidin-4-one
• CAS: 5719-24-4
• 化学式: C₁₂H₁₀N₂OS
• 分子量: 230.29
• InChiKey: KZLGPDODLDYACG-UHFFFAOYSA-N

物化性质

• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-ol 在 三乙胺 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 4-chloro-2-phenyl-5,7-dihydrothieno<3,4-d>pyrimidine 6,6-dioxide
  参考文献：
  名称：

  嘧啶原喹啉二甲烷

  摘要：

  嘧啶砜10，R = Me; Nu = OMe，NEt 2，SPh，H和11，R = Ph；由二氢噻吩并嘧啶酮7（R = Me，Ph）转化为氯衍生物8，然后用mCPBA氧化并与适当的亲核试剂或氢和Pd反应，合成Nu = OMe 。在1,2,4-三氯苯中加热砜，得到嘧啶-邻-喹二甲烷，其在狄尔斯-阿尔德反应中截获，得到四氢喹唑啉。

  DOI：

  10.1016/0040-4020(95)01009-2
• 作为产物：
  描述：

  4-氧四氢噻酚-3-羧酸甲酯 、 苄脒盐酸盐 在 sodium ethanolate 作用下， 生成 2-phenyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-ol
  参考文献：
  名称：

  Diels-Alder和Michael加成中的5,6-二亚甲基嘧啶-4-酮的生成和捕获

  摘要：

  嘧啶酮稠合砜5 - 7从脒与3-甲氧羰基-4- oxotetrahydrothiophene反应制得，随后加入N-甲基化和氧化用mCPBA。对在150℃下将溶液加热，SO的挤出2发生，得到高反应性的，其被拦截5,6- dimethylenepyrimidin -4-酮在原位在狄尔斯-阿尔德反应，得到加合物24 - 28和在共轭加成反应与巯基亲核素一起生成硫醚29和30。

  DOI：

  10.1016/0040-4020(95)01008-4

文献信息

• Identification of the fused bicyclic 4-amino-2-phenylpyrimidine derivatives as novel and potent PDE4 inhibitors
  作者：Taiji Goto、Akiko Shiina、Toshiharu Yoshino、Kiyoshi Mizukami、Kazuki Hirahara、Osamu Suzuki、Yoshitaka Sogawa、Tomoko Takahashi、Tsuyoshi Mikkaichi、Naoki Nakao、Mizuki Takahashi、Masashi Hasegawa、Shigeki Sasaki

  DOI：10.1016/j.bmcl.2013.03.104

  日期：2013.6

  2-Phenyl-4-piperidinyl-6,7-dihydrothieno[3,4-d] pyrimidine derivative (2) was found to be a new PDE4 inhibitor with moderate PDE4B activity (IC50 = 150 nM). A number of derivatives with a variety of 4-amino substituents and fused bicyclic pyrimidines were synthesized. Among these, 5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivative (18) showed potent PDE4B inhibitory activity (IC50 = 25 nM). Finally, N-propylacetamide derivative (31b) was determined as a potent inhibitor for both PDE4B (IC50 = 7.5 nM) and TNF-alpha production in mouse splenocytes (IC50 = 9.8 nM) and showed good in vivo anti-inflammatory activity in the LPS-induced lung inflammation model in mice (ID50 = 18 mg/kg). The binding mode of the new inhibitor (31e) in the catalytic site of PDE4B is presented based on an X-ray crystal structure of the ligand-enzyme complex. (C) 2013 Elsevier Ltd. All rights reserved.
• Generation and trapping of 5,6-dimethylenepyrimidin-4-ones in Diels-Alder and Michael additions
  作者：Augusto C. Tomé、Cavaleiro José A.S、Richard C. Storr

  DOI：10.1016/0040-4020(95)01008-4

  日期：1996.1

  followed by N-methylation and oxidation with mCPBA. On heating in solution at 150°C, extrusion of SO2 occured to give the highly reactive 5,6-dimethylenepyrimidin-4-ones which were intercepted in situ in Diels-Alder reactions to give the adducts 24–28 and in conjugate addition reactions with thiol nucleophiles to give the thioethers 29 and 30.

  嘧啶酮稠合砜5 - 7从脒与3-甲氧羰基-4- oxotetrahydrothiophene反应制得，随后加入N-甲基化和氧化用mCPBA。对在150℃下将溶液加热，SO的挤出2发生，得到高反应性的，其被拦截5,6- dimethylenepyrimidin -4-酮在原位在狄尔斯-阿尔德反应，得到加合物24 - 28和在共轭加成反应与巯基亲核素一起生成硫醚29和30。
• Pyrimidine ortho-quinodimethanes
  作者：Augusto C. Tomé、José A.S. Cavaleiro、Richard C. Storr

  DOI：10.1016/0040-4020(95)01009-2

  日期：1996.1

  The pyrimidine sulfones 10, R = Me; Nu = OMe, NEt2, SPh, H and 11, R = Ph; Nu = OMe were synthesised from the dihydrothienopyrimidones 7, R = Me, Ph by conversion to the chloro derivatives 8 followed by oxidation with mCPBA and reaction with the appropriate nucleophile or hydrogen and Pd. Heating of the sulfones in 1,2,4-trichlorobenzene gave the pyrimidine o-quinodimethanes which were intercepted

  嘧啶砜10，R = Me; Nu = OMe，NEt 2，SPh，H和11，R = Ph；由二氢噻吩并嘧啶酮7（R = Me，Ph）转化为氯衍生物8，然后用mCPBA氧化并与适当的亲核试剂或氢和Pd反应，合成Nu = OMe 。在1,2,4-三氯苯中加热砜，得到嘧啶-邻-喹二甲烷，其在狄尔斯-阿尔德反应中截获，得到四氢喹唑啉。