N-Phenyliden-β-phenaethylamin | 97408-38-3

• 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: N-Phenyliden-β-phenaethylamin
• 英文别名: N-pentylidene-2-phenylethanamine
• CAS: 97408-38-3
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: YOWANQWDOLDXTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-Phenyliden-β-phenaethylamin 、 甲乙酐 生成
  参考文献：
  名称：

  Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline derivatives on PC12 cells

  摘要：

  The synthesis of several 1-alkyl-1,2,3,4-tetrahydroisoquinolines, which may play an important role in Parkinson's disease, has been achieved by modified Pictet-Spengler cyclization of the formyliminium ion. The direct cytotoxicity and preventative effects towards MPP+-mediated death of PC12 cells were estimated. The cytotoxicities of 1-alkyl-TIQs were apoptotic and depended on their lipophilic properties. Conversely, introducing the N-propargyl substituent reduced cytotoxicity. 1-Methyl-, 1-methyl-N-propargyl- and 1-cyclopropyl-TIQ partially inhibited MPP+-induced cell death, whereas relatively large alkyl substituents at the first position did not enhance the viability of PC12 cells. In summary, our findings suggest a crucial role for the N-propargyl functional group for the effective reduction of cytotoxicity, and show the importance of size and lipophilicity of substituents at the 1-position of 1-alkyl TIQs. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.035
• 作为产物：
  描述：

  正戊醛 、 2-苯乙胺 在 titanium(IV) isopropylate 作用下， 反应 1.0h， 生成 N-Phenyliden-β-phenaethylamin
  参考文献：
  名称：

  Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline derivatives on PC12 cells

  摘要：

  The synthesis of several 1-alkyl-1,2,3,4-tetrahydroisoquinolines, which may play an important role in Parkinson's disease, has been achieved by modified Pictet-Spengler cyclization of the formyliminium ion. The direct cytotoxicity and preventative effects towards MPP+-mediated death of PC12 cells were estimated. The cytotoxicities of 1-alkyl-TIQs were apoptotic and depended on their lipophilic properties. Conversely, introducing the N-propargyl substituent reduced cytotoxicity. 1-Methyl-, 1-methyl-N-propargyl- and 1-cyclopropyl-TIQ partially inhibited MPP+-induced cell death, whereas relatively large alkyl substituents at the first position did not enhance the viability of PC12 cells. In summary, our findings suggest a crucial role for the N-propargyl functional group for the effective reduction of cytotoxicity, and show the importance of size and lipophilicity of substituents at the 1-position of 1-alkyl TIQs. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.035

文献信息

• Direct Synthesis of Imines from Alcohols and Amines with Liberation of H2
  作者：Boopathy Gnanaprakasam、Jing Zhang、David Milstein

  DOI：10.1002/anie.200907018

  日期：2010.2.15

  A clean sweep: Aryl and aliphatic imines can be synthesized directly and efficiently from alcohols and amines under mild, neutral conditions with the liberation of only molecular hydrogen and water (see scheme; R=isopropyl, tert‐butyl). This general, environmentally benign reaction is catalyzed by a de‐aromatized ruthenium PNP pincer complex (0.2 mol %), and can proceed in toluene under an inert atmosphere

  一目了然：在温和的中性条件下，醇和胺可仅由分子氢和水释放（见方案； R =异丙基，叔丁基），可直接有效地由醇和胺合成芳基和脂族亚胺。这种一般的，对环境无害的反应是由脱芳香化的钌PNP钳形配合物（0.2摩尔％）催化的，可以在甲苯中于惰性气氛或空气中进行。