2-Phenyl-tetrahydrobenzimidazol | 26663-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Phenyl-tetrahydrobenzimidazol
• 英文别名: 2-phenyl-4,5,6,7-tetrahydro-1H-benzimidazole
• CAS: 26663-56-9
• 化学式: C₁₃H₁₄N₂
• mdl: MFCD19315099
• 分子量: 198.268
• InChiKey: BACJJTXQMLXPKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Phenyl-tetrahydrobenzimidazol 、 对氟苯甲砜 在 aluminum oxide 、 potassium fluoride 、 18-冠醚-6 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以55%的产率得到1-(4-methylsulfonyl)-2-phenyl-4,5,6,7-tetrahydrobenzimidazole
  参考文献：
  名称：

  Synthesis of N‐Aryl‐2‐substituted Tetrahydrobenzimidazoles via Direct N‐Arylation

  摘要：

  A series of novel N-aryl-2-substituted tetrahydrobenzimidazoles has been synthesized via direct N-arylation of 2-substituted tetrahydrobenzimidazoles, which was accomplished by a medium aryl electrophile, 4-methylsulfonylfluorobenze, in the presence of 37% KF/Al2O3 and 18-crown-6 in fair yields under mild reaction conditions. Meanwhile, the hydrogenation of 2-phenylbenzimidazole was studied.

  DOI：

  10.1080/00397910601168249
• 作为产物：
  描述：

  1-(2-ethoxycarbonyl-2-iodo-1-phenylethyl)-5-phenyltetrazole 在 sodium ethanolate 、 甲基三苯基碘化膦 、 三丁基氧化锡 、 sodium iodide 作用下， 以 六甲基磷酰三胺 、 乙醇 、 Petroleum ether 为溶剂， 反应 196.75h， 生成 2-Phenyl-tetrahydrobenzimidazol
  参考文献：
  名称：

  Casey, Michael; Moody, Christopher J.; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1933 - 1941

  摘要：

  DOI：
• 作为试剂：
  描述：

  苄脒盐酸盐 、 2-羟基环己酮二聚物 在 2-Phenyl-tetrahydrobenzimidazol 作用下， 以 ammonium hydroxide 为溶剂， 反应 7.0h， 以yielded 3.0 g 2-phenyl-4,5,6,7,-tetrahydrobenzimidazole (Compound 136), m.p. 300-301° C.的产率得到2-Phenyl-tetrahydrobenzimidazol
  参考文献：
  名称：

  Certain 4-aminomethyl-2-substituted imidazole derivatives and

  摘要：

  本发明涉及以下化合物：##STR1##其中，R.sub.1代表可选取代的芳基，杂环芳基，芳基烷基或环烷基基团；X，Z和Y是可选取代的氮或碳原子；R.sub.3和R.sub.4是有机或无机取代基，可以共同形成环结构；m为零，一或二；R.sub.5和R.sub.6是有机或无机取代基；以及其药学上可接受的盐，这些化合物在大脑多巴胺受体亚型上是高度选择性的部分激动剂或拮抗剂，或其前药，可用于诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森症。

  公开号：

  US06069251A1

文献信息

• Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives: new classes of dopamine receptor subtype specific ligands
  申请人：Neurogen Corporation, Corporation of the State of Delaware

  公开号：US20030018025A1

  公开（公告）日：2003-01-23

  Disclosed are compounds of the formula: 1 wherein R 1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y are optionally substituted nitrogen or carbon atoms; R 3 and R 4 are organic or inorganic substitutents which may togther form ring structutes; m is zero, one or two; and R 5 and R 6 are are organic or inorganic substituents; and the pharmaceutically acceptable addition salts thereof, which compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism.

  揭示了以下式的化合物： 其中R1代表可选择地取代的芳基、杂环芳基、芳基烷基或环烷基基团；X、Z和Y为可选择地取代的氮或碳原子；R3和R4为有机或无机取代基，可能共同形成环结构；m为零、一或二；R5和R6为有机或无机取代基； 以及其药学上可接受的盐， 这些化合物是高度选择性的部分激动剂或拮抗剂，作用于脑多巴胺受体亚型或其前药，并可用于诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。
• A new synthesis of imidazoles
  作者：Michael Casey、Christopher J. Moody、Charles W. Rees

  DOI：10.1039/c39820000714

  日期：——

  Alkenes are converted into imidazoles through their epoxides by treatment with 2-tri-n-butylstannyltetrazoles (2), followed by dehydration with methyltriphenoxyphosphonium iodide in an improved procedure, and photolysis of the resulting vinyltetrazoles (4).

  烯烃通过其环氧化物与2-三正丁基锡四氮唑（2）反应，随后采用改进的方法与三甲基苯氧基磷阳离子碘化物脱水，最后对所得的乙烯基四氮唑（4）进行光解，转化为咪唑。
• 4-piperidino- and piperazinomethyl-2-cyclohexyl imidazole derivatives;
  申请人：Neurogen Corporation

  公开号：US05633377A1

  公开（公告）日：1997-05-27

  Disclosed are compounds of the formula: ##STR1## wherein R.sub.1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y are optionally substituted nitrogen or carbon atoms; R.sub.3 and R.sub.4 are organic or inorganic substitutents which may together form ring structures; m is zero, one or two; and R.sub.5 and R.sub.6 are are organic or inorganic substituents; and the pharmaceutically acceptable addition salts thereof, which compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism.

  本发明涉及一种公式为：##STR1##的化合物，其中R.sub.1代表可选取代的芳基、杂环芳基、芳基烷基或环烷基基团；X、Z和Y是可选取代的氮或碳原子；R.sub.3和R.sub.4是有机或无机取代基，它们可以一起形成环结构；m为零、一或二；R.sub.5和R.sub.6是有机或无机取代基；以及其药学上可接受的盐。这些化合物是高度选择性的部分激动剂或拮抗剂，可作为脑多巴胺受体亚型或其前药在情感障碍，如精神分裂症和抑郁症以及某些运动障碍，如帕金森症的诊断和治疗中使用。
• Certain 4-piperidino- and piperazinomethyl-2-phenyl imidazole
  申请人：Neurogen Corporation

  公开号：US05646281A1

  公开（公告）日：1997-07-08

  Disclosed are compounds of the formula: ##STR1## wherein R.sub.1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y are optionally substituted nitrogen or carbon atoms; R.sub.3 and R.sub.4 are organic or inorganic substituents which may together form ring structures; m is zero, one or two; and R.sub.5 and R.sub.6 are are organic or inorganic substituents; and the pharmaceutically acceptable addition salts thereof, which compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism.

  本发明涉及以下化合物：##STR1## 其中R.sub.1代表可选取代的芳基，杂环芳基，芳基烷基或环烷基基团；X，Z和Y是可选取代的氮或碳原子；R.sub.3和R.sub.4是有机或无机取代基，可以共同形成环结构；m为零、一或二；R.sub.5和R.sub.6是有机或无机取代基；以及其药学上可接受的加合盐。这些化合物是高度选择性的部分激动剂或拮抗剂，可作为脑多巴胺受体亚型的诊断和治疗工具，用于情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。
• 4-piperidino-and piperazinomethyl-2-phenylimidazole derivatives,
  申请人：Neurogen Corporation

  公开号：US05656762A1

  公开（公告）日：1997-08-12

  Disclosed are compounds of the formula: ##STR1## wherein R.sub.1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y optionally substituted nitrogen or carbon atoms; R.sub.3 and R.sub.4 are organic or inorganic substitutents which may together form ring structures; m is zero, one or two; and R.sub.5 and R.sub.6 are are organic or inorganic substituents; and the pharmaceutically acceptable addition salts thereof, which compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism.

  本发明涉及以下式的化合物：##STR1## 其中，R.sub.1代表可选择取代的芳基，杂环芳基，芳基烷基或环烷基基团；X，Z和Y是可选择取代的氮或碳原子；R.sub.3和R.sub.4是有机或无机取代基，它们可以一起形成环状结构；m为零，一或二；而R.sub.5和R.sub.6是有机或无机取代基；以及其药学上可接受的加合盐，这些化合物是高度选择性的部分激动剂或拮抗剂，在脑多巴胺受体亚型或其前药中有用，可用于诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。