N-formyl-1-N-pentyl-1,2,3,4-tetrahydroisoquinoline | 134253-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: N-formyl-1-N-pentyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-pentyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
• CAS: 134253-37-5
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: YJUHXNCNSFKLIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-formyl-1-N-pentyl-1,2,3,4-tetrahydroisoquinoline 在 乙醇 、 sodium hydroxide 作用下， 反应 3.0h， 以90%的产率得到1-pentyl-1,2,3,4-tetrahydroisoquinoline
  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：

  3-(1-Pentyl-3,4-dihydro-1H-isoquinolin-2-yl)-butan-2-ol 在 四丁基溴化铵 sodium hydroxide 作用下， 以 氯仿 为溶剂， 以60%的产率得到N-formyl-1-N-pentyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  碳α转化为仲胺氮的新烷基化方法

  摘要：

  提出了一种将碳α烷基化为仲胺1a，c-g的氮的方法，该方法基于从β-羟基叔胺N-氧化物2高效合成新的恶唑烷3的方法。

  DOI：

  10.1016/0040-4039(91)80353-8

文献信息

• A new alkylation method of the carbon α to the nitrogen of secondary amines
  作者：Georges Roussi、Jidong Zhang

  DOI：10.1016/0040-4039(91)80353-8

  日期：1991.3

  A route to the alkylation of the carbon α to the nitrogen of secondary amines 1a,c–g is proposed which is based upon a new and efficient synthesis of oxazolidines 3 from β- hydroxy tertiary amine N-oxides 2.

  提出了一种将碳α烷基化为仲胺1a，c-g的氮的方法，该方法基于从β-羟基叔胺N-氧化物2高效合成新的恶唑烷3的方法。
• Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline derivatives on PC12 cells
  作者：Michikazu Kitabatake、Junko Nagai、Kenji Abe、Yukihiro Tsuchiya、Keita Ogawa、Takashi Yokoyama、Kunihiko Mohri、Kyoji Taguchi、Yoshie Horiguchi

  DOI：10.1016/j.ejmech.2009.04.035

  日期：2009.10

  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.