2-<(4-chloromethyl)-2-phenyl-1,3-dioxolan-2-yl>-α-<(dimethylamino)methylene>-β-oxobenzenepropanenitrile | 76988-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-<(4-chloromethyl)-2-phenyl-1,3-dioxolan-2-yl>-α-<(dimethylamino)methylene>-β-oxobenzenepropanenitrile
• 英文别名: 2-[4-(Chloromethyl)-2-phenyl-1,3-dioxolan-2-yl]-alpha-[(dimethylamino)methylene]-beta-oxo-benzenepropanenitrile；2-[2-[4-(chloromethyl)-2-phenyl-1,3-dioxolan-2-yl]benzoyl]-3-(dimethylamino)prop-2-enenitrile
• CAS: 76988-35-7
• 化学式: C₂₂H₂₁ClN₂O₃
• 分子量: 396.873
• InChiKey: FJDQLQOPHGGOKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<(4-chloromethyl)-2-phenyl-1,3-dioxolan-2-yl>-α-<(dimethylamino)methylene>-β-oxobenzenepropanenitrile 在 镍 盐酸 、 manganese(IV) oxide 、 氢气 作用下， 反应 14.0h， 生成 7-phenyl-5H-pyrimido<5,4-d><2>benzazepin-2-amine
  参考文献：
  名称：

  2-苯并ze庚因。7.嘧啶并[5,4- d ] [2]苯并ze庚因的合成†

  摘要：

  描述了嘧啶并[5,4- d ] [2]苯并ze庚因的两种新颖合成方法。第一次合成以3-苯基邻苯二甲酸酯开始，其在三个步骤中被转化为官能化的嘧啶，其被环化以生成2-苯并ze庚因环系统。第二种方法使用邻苯甲酰基苯甲酸甲酯作为起始原料，在四个步骤中将其转化为官能化的嘧啶，将其环化以生成2-苯并ze庚因。嘧啶[5,4- d ] [2]苯并tests庚因在标准中枢神经系统（CNS）药理试验中具有活性。

  DOI：

  10.1002/jhet.5570200512
• 作为产物：
  描述：

  邻苯甲酰苯甲酸甲酯 在 四氯化锡 、 sodium amide 作用下， 以 四氯化碳 为溶剂， 反应 3.5h， 生成 2-<(4-chloromethyl)-2-phenyl-1,3-dioxolan-2-yl>-α-<(dimethylamino)methylene>-β-oxobenzenepropanenitrile
  参考文献：
  名称：

  2-苯并ze庚因。7.嘧啶并[5,4- d ] [2]苯并ze庚因的合成†

  摘要：

  描述了嘧啶并[5,4- d ] [2]苯并ze庚因的两种新颖合成方法。第一次合成以3-苯基邻苯二甲酸酯开始，其在三个步骤中被转化为官能化的嘧啶，其被环化以生成2-苯并ze庚因环系统。第二种方法使用邻苯甲酰基苯甲酸甲酯作为起始原料，在四个步骤中将其转化为官能化的嘧啶，将其环化以生成2-苯并ze庚因。嘧啶[5,4- d ] [2]苯并tests庚因在标准中枢神经系统（CNS）药理试验中具有活性。

  DOI：

  10.1002/jhet.5570200512

文献信息

• Pyrimido-2-benzazepines
  申请人：Hoffmann-La Roche Inc.

  公开号：US04481142A1

  公开（公告）日：1984-11-06

  There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group--NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and dilower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.9 are hydrogen or lower alkyl; n is 0 or 1 and m is 1 to 7 with the limitations that (1) at least one of R.sub.1 and R.sub.2 are hydrogen, (2) when R.sub.3 is lower acyloxy or hydroxy, A is the group (a), X is hydrogen, halogen, trifluoromethyl, ethyl or acetyl and R.sub.1 is the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, then R.sub.8 and R.sub.9 are lower alkyl, (3) when A is group (d) and R.sub.1 is the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9 then R.sub.8 and R.sub.9 are lower alkyl and (4) when n is 1, R.sub.1 is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine or the group --CH.sub.2 --CO-- R.sub.7 with R.sub.7 as above then A is the group (a) or (b) and the pharmaceutically acceptable salts thereof. The compounds exhibit pharmacological activity as anxiolytics and sedatives. Also presented Are various novel intermediates and processes to produce the above end products.

  该文中介绍了一些化合物，其化学式为##STR1## 其中A从以下组中选择：##STR2## R1从以下组中选择：氢、氯、溴、低碳基、基团NR4R5、基团--CH2--CO--R7、基团--NH(CH2)mNR8R9、羟基、低烷氧基、巯基和低烷基巯基；R2从以下组中选择：氢、氨基和二低烷基氨基；R3从以下组中选择：氢、低酰氧基和羟基；X从以下组中选择：氢、卤素、三氟甲基、乙基、α-羟基乙基和乙酰基；Y为氢或卤素；R4和R5为氢或低烷基，或与它们共键合的氮原子形成五元至七元杂环基团；R7从以下组中选择：羟基低烷氧基和NR8R9；R8和R9为氢或低烷基；n为0或1，m为1至7，限制为：(1)R1和R2中至少有一个为氢；(2)当R3为低酰氧基或羟基时，A为(a)组，X为氢、卤素、三氟甲基、乙基或乙酰基，R1为基团--NH(CH2)mNR8R9，则R8和R9为低烷基；(3)当A为(d)组，R1为基团--NH(CH2)mNR8R9时，则R8和R9为低烷基；(4)当n为1，R1为氢、低烷基、低烷氧基、氯、溴或基团--CH2--CO--R7，其中R7如上所述，则A为(a)或(b)组及其药学上可接受的盐。这些化合物表现出抗焦虑和镇静的药理活性。此外，还介绍了各种新型中间体和生产上述终产品的工艺。
• Pyrimido-2-benzazepines and intermediates in their preparation
  申请人：Hoffmann-La Roche Inc.

  公开号：US04547581A1

  公开（公告）日：1985-10-15

  There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and di-lower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.9 are hydrogen or lower alkyl; n is 0 or 1 and m is 1 to 7 with the limitations that (1) at least one of R.sub.1 and R.sub.2 are hydrogen, (2) when R.sub.3 is lower acyloxy or hydroxy, A is the group (a), X is hydrogen, halogen, trifluoromethyl, ethyl or acetyl and R.sub.1 is the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, then R.sub.8 and R.sub.9 are lower alkyl, (3) when A is group (d) and R.sub.1 is the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9 then R.sub.8 and R.sub.9 are lower alkyl and (4) when n is 1, R.sub.1 is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine or the group --CH.sub.2 --CO--R.sub.7 with R.sub.7 as above then A is the group (a) or (b) and the pharmaceutically acceptable salts thereof. The compounds exhibit pharmacological activity as anxiolytics and sedatives. Also presented are various novel intermediates and processes to produce the above end products.

  该文献介绍了公式为##STR1##的化合物，其中A选自以下组中的一种：##STR2## R.sub.1选自以下组中的一种：氢、氯、溴、低烷基、基团NR.sub.4 R.sub.5、基团--CH.sub.2 --CO--R.sub.7、基团--NH(CH.sub.2).sub.m NR.sub.8 R.sub.9、羟基、低烷氧基、巯基和低烷基巯基；R.sub.2选自以下组中的一种：氢、氨基和二低烷基氨基；R.sub.3选自以下组中的一种：氢、低酰氧基和羟基；X选自以下组中的一种：氢、卤素、三氟甲基、乙基、α-羟乙基和乙酰基；Y为氢或卤素；R.sub.4和R.sub.5为氢或低烷基，或与它们的共键氮原子形成五元至七元杂环基团；R.sub.7选自以下组中的一种：羟基低烷氧基和NR.sub.8 R.sub.9；R.sub.8和R.sub.9为氢或低烷基；n为0或1，m为1至7，限制条件为（1）R.sub.1和R.sub.2中至少有一个为氢，（2）当R.sub.3为低酰氧基或羟基时，A为组（a），X为氢、卤素、三氟甲基、乙基或乙酰基，R.sub.1为基团--NH(CH.sub.2).sub.m NR.sub.8 R.sub.9，则R.sub.8和R.sub.9为低烷基，（3）当A为组（d）且R.sub.1为基团--NH(CH.sub.2).sub.m NR.sub.8 R.sub.9时，则R.sub.8和R.sub.9为低烷基，（4）当n为1，R.sub.1为氢、低烷基、低烷氧基、氯、溴或基团--CH.sub.2 --CO--R.sub.7（其中R.sub.7如上所述）时，A为组（a）或（b），以及其药学上可接受的盐。这些化合物表现出抗焦虑和镇静的药理活性。此外，还提供了各种新颖的中间体和生产上述终产品的过程。
• 2-Benzazepines. 7. Synthesis of pyrimido[5,4-<i>d</i>][2]benzazepines
  作者：James V. Earley、R. Ian Fryer、Norman W. Gilman

  DOI：10.1002/jhet.5570200512

  日期：1983.9

  pyrimido[5,4-d][2]benzazepines are described. The first synthesis started with 3-phenylphthalide which in three steps was converted to a functionalized pyrimidine which was cyclized to give the 2-benzazepine ring system. The second approach used o-benzoylbenzoic acid methyl ester as the starting material, which in four steps was converted to a functionalized pyrimidine which was cyclized to give a 2-benzazepine

  描述了嘧啶并[5,4- d ] [2]苯并ze庚因的两种新颖合成方法。第一次合成以3-苯基邻苯二甲酸酯开始，其在三个步骤中被转化为官能化的嘧啶，其被环化以生成2-苯并ze庚因环系统。第二种方法使用邻苯甲酰基苯甲酸甲酯作为起始原料，在四个步骤中将其转化为官能化的嘧啶，将其环化以生成2-苯并ze庚因。嘧啶[5,4- d ] [2]苯并tests庚因在标准中枢神经系统（CNS）药理试验中具有活性。