1-环丁基-1,2,3,4-四氢异喹啉 | 886759-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 1-环丁基-1,2,3,4-四氢异喹啉
• 英文名称: 1-Cyclobutyl-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 1-Cyclobutyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 886759-47-3
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: BZKHQILNYWQRIO-UHFFFAOYSA-N

物化性质

• 沸点：
  303.7±11.0 °C(Predicted)
• 密度：
  1.058

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1-环丁基-1,2,3,4-四氢异喹啉 、 3-溴丙炔 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以67%的产率得到1-cyclobutyl-2-propargyl-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：

  环丁基苯(基甲)酮 在 titanium(IV) isopropylate 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 三氟化硼乙醚 、 三氟乙酸酐 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 苯 为溶剂， 反应 30.0h， 生成 1-环丁基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  1,2,3,4-四氢异喹啉衍生物的合成及体外细胞毒性。

  摘要：

  几种可能在帕金森氏病中起作用的1-烷基-1,2,3,4-四氢异喹啉（TIQ）衍生物是通过Pummerer型环化由N-甲酰基亚砜就地形成的sulf离子合成的。使用体外锥虫蓝排斥试验，发现高浓度的TIQ衍生物在C-1位具有显着的烷基取代基，例如1-环丁基-，1-环己基-，1-苯基-或1-苄基-影响PC12细胞的生存能力。此外，中度或强烈诱导凋亡的TIQ衍生物（例如分别为1-苯基-TIQ和1-环己基-TIQ）与使用锥虫蓝排除试验获得的结果相平行。这些结果表明，官能团的大小和给电子性质可能会影响TIQ衍生物的细胞毒性。

  DOI：

  10.1016/j.ejmech.2005.11.003

文献信息

• Synthesis and in vitro cytotoxicity of 1,2,3,4-tetrahydroisoquinoline derivatives
  作者：Toshiaki Saitoh、Kenji Abe、Masami Ishikawa、Masanao Nakatani、Seiichiro Shimazu、Noriyuki Satoh、Fumio Yoneda、Kyoji Taguchi、Yoshie Horiguchi

  DOI：10.1016/j.ejmech.2005.11.003

  日期：2006.2

  Several 1-alkyl-1,2,3,4-tetrahydroisoquinoline (TIQ) derivatives, which may play a role in Parkinson's disease, have been synthesized via Pummerer-type cyclization of the sulfonium ion formed in situ from N-formyl sulfoxide. Using an in vitro trypan blue exclusion assay, high concentrations of TIQ derivatives possessing bulky alkyl group substituents such as 1-cyclobutyl-, 1-cyclohexyl-, 1-phenyl-

  几种可能在帕金森氏病中起作用的1-烷基-1,2,3,4-四氢异喹啉（TIQ）衍生物是通过Pummerer型环化由N-甲酰基亚砜就地形成的sulf离子合成的。使用体外锥虫蓝排斥试验，发现高浓度的TIQ衍生物在C-1位具有显着的烷基取代基，例如1-环丁基-，1-环己基-，1-苯基-或1-苄基-影响PC12细胞的生存能力。此外，中度或强烈诱导凋亡的TIQ衍生物（例如分别为1-苯基-TIQ和1-环己基-TIQ）与使用锥虫蓝排除试验获得的结果相平行。这些结果表明，官能团的大小和给电子性质可能会影响TIQ衍生物的细胞毒性。
• 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.