2-phenyl-4,5,6,7-tetrahydro-1H-1,3-diazepine | 76894-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮卓类
• 英文名称: 2-phenyl-4,5,6,7-tetrahydro-1H-1,3-diazepine
• 英文别名: 2-phenyl-1,3-diazacycloheptene；2-phenyl-2,7-diazacycloheptene；2-phenyl-4,5,6,7-tetrahydro-1H-[1,3]diazepine；2-Phenyl-4,5,6,7-tetrahydro-1H-[1,3]diazepin；4,5,6,7-Tetrahydro-2-phenyl-1H-1,3-diazepine
• CAS: 76894-37-6
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: YPSSKZYWAMIXNE-UHFFFAOYSA-N

物化性质

• 沸点：
  329.7±15.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-4,5,6,7-tetrahydro-1H-1,3-diazepine 以 乙醇 为溶剂， 反应 60.0h， 以95%的产率得到N-(4-氨基丁基)苯甲酰胺
  参考文献：
  名称：

  碱性，亲脂性，并且受体的缺乏相互作用Ñ -Aminoalkylbenzamides和Ñ -Aminoalkyl- ö -anisamides作为多巴胺拮抗剂的模型化合物

  摘要：

  Ñ -Aminoalkylbenzamides和Ñ -aminoalkyl- ö -methoxybenzamides已经制备并检测它们的p ķ一个，登录P和多巴胺受体的亲和性。p K a值的范围从ca。对于具有一个-C原子侧链的衍生物，为约7.5 。10.3为N-氨基丁基衍生物。链长的这些变化可以通过现场模型得到令人满意的解释。（log P）值的变化作为链长和N原子取代的函数，表明存在邻近和构象效应。化合物完全不能取代来自其特定的大鼠纹状体结合位点的3 H-哌啶酮和3 H-磺胺必隆证明了在位置4和5进行足够的芳族取代的关键作用。

  DOI：

  10.1002/hlca.19830660215
• 作为产物：
  描述：

  苯甲酸酐 在 bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt 作用下， 以 二氯甲烷 为溶剂， 反应 36.08h， 生成 2-phenyl-4,5,6,7-tetrahydro-1H-1,3-diazepine
  参考文献：
  名称：

  Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

  摘要：

  Methods for the cydodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.

  DOI：

  10.1021/jo401082q

文献信息

• Use of lanthanide(III) ions as catalysts for the reactions of amines with nitriles
  作者：John H. Forsberg、Vincent T. Spaziano、Trichey M. Balasubramanian、Gordon K. Liu、Steven A. Kinsley、Charles A. Duckworth、John J. Poteruca、Paul S. Brown、Judith L. Miller

  DOI：10.1021/jo00382a009

  日期：1987.3
• 96. Amidines. Part VI. Preparation of 2-substituted 4 : 5-dihydroglyoxalines and ring homologues from cyanides and alkylenediamines
  作者：P. Oxley、W. F. Short

  DOI：10.1039/jr9470000497

  日期：——
• Basicity, Lipophilicity, and Lack of Receptor Interaction ofN-Aminoalkylbenzamides andN-Aminoalkyl-o-anisamides as Model Compounds of Dopamine Antagonists
  作者：Lucien Anker、Bernard Testa、Han Van De Waterbeemd、Anne Bornand-Crausaz、Andreas Theodorou、Peter Jenner、C. David Marsden

  DOI：10.1002/hlca.19830660215

  日期：1983.3.16

  N-aminoalkyl-o-methoxybenzamides have been prepared and examined for their pKa, log P and dopamine receptor affinity. The pKa values range from ca. 7.5 for the derivatives having a one-C-atom side-chain, to ca. 10.3 for the N-aminobutyl derivatives. These variations with chain length are satisfactoryly explained by a field model. The variations in (log P)-values as a function of chain length and substitution

  Ñ -Aminoalkylbenzamides和Ñ -aminoalkyl- ö -methoxybenzamides已经制备并检测它们的p ķ一个，登录P和多巴胺受体的亲和性。p K a值的范围从ca。对于具有一个-C原子侧链的衍生物，为约7.5 。10.3为N-氨基丁基衍生物。链长的这些变化可以通过现场模型得到令人满意的解释。（log P）值的变化作为链长和N原子取代的函数，表明存在邻近和构象效应。化合物完全不能取代来自其特定的大鼠纹状体结合位点的3 H-哌啶酮和3 H-磺胺必隆证明了在位置4和5进行足够的芳族取代的关键作用。
• Cyclodehydration of <i>N</i>-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue
  作者：Wendy A. Loughlin、Ian D. Jenkins、Maria J. Petersson

  DOI：10.1021/jo401082q

  日期：2013.7.19

  Methods for the cydodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.