1-n-butyl-1,2,3,4-tetrahydroisoquinoline | 78702-75-7

• 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: 1-n-butyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-butyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 78702-75-7
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: NEMBFAJWTUSZDU-UHFFFAOYSA-N

物化性质

• 沸点：
  85 °C(Press: 1.5 Torr)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• 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

反应信息

• 作为反应物：
  描述：

  1-n-butyl-1,2,3,4-tetrahydroisoquinoline 、 3-溴丙炔 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以59%的产率得到1-n-butyl-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：

  2-(4,5-dihydro-thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline 在 一水合肼 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 1-n-butyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  4,5-二氢噻唑啉——生成仲胺α-氨基碳负离子的新型保护和活化基团

  摘要：

  摘要 4,5-二氢噻唑啉已成功用作保护和活化基团，通过锂化-亲电取代反应序列合成各种1-取代的1,2,3,4-四氢异喹啉。

  DOI：

  10.1080/00397910600941331

文献信息

• 2-Bis (dimethylamino)phosphinoyl-1-lithio-1, 2, 3, 4-tetrahydroisoquinoline. A highly nucleophilic d1-reagent for the preparation of 1-substituted tetrahydroisoquinolines
  作者：Dieter Seebach、Masaaki Yoshifuji

  DOI：10.1002/hlca.19810640305

  日期：1981.4.29

  reactions with electrophiles furnish the products 6–22, 26, 27, see Table 1 and the Scheme. A second alkylation is also possible, see 23–25. The cleavage to tetrahydroisoquinolines is accomplished in refluxing aqueous-methanolic hydrochloric acid, see Table 2. Phosphinoylation, lithiation, reaction with electrophiles and cleavage constitute an efficient sequence for 1-alkylation of the isoquinoline nucleus

  标题化合物4由磷酸酰胺5在四氢呋喃中与丁基锂生成。锂试剂4在室温下稳定。其与亲电反应提供产品6-22，26，27，参见表1和方案。第二次烷基化也是可能的，请参阅23–25。在回流的含水甲醇盐酸中完成四氢异喹啉的裂解，参见表2。膦酰基化，锂化，与亲电试剂反应和裂解构成异喹啉核1烷基化的有效序列。
• Carbon dioxide: A reagent for the protection of nucleophilic centres and the simultaneous activation of electrophilic attack
  作者：Alan R. Katritzky、Kunihiko Akutagawa

  DOI：10.1016/0040-4020(86)80024-2

  日期：1986.1

  Tetrahydroisoquinoline was converted into several 1-substituted derivatives by using carbon dioxide both for N-protection and to give an intermediate carbanion stabilizing group. t-Butyllithium was used as a lithating agent at the alphacarbon atom of the secondary amino group. The resulting 1-substituted 1,2,3,4-tetrahydroisoquinoline-2-carboxylic acids underwent smooth acid-catalysed decarboxylation

  通过使用二氧化碳进行N-保护和提供中间碳负离子稳定基团，将四氢异喹啉转化为几种1-取代的衍生物。在仲氨基的α碳原子处，叔丁基锂被用作锂化剂。在温和的条件下，将所得的1-取代的1,2,3,4-四氢异喹啉-2-羧酸进行平滑的酸催化脱羧。
• Alkylation of the isoquinoline skeleton in the 1-position
  作者：Dieter Seebach、Jean-Jacques Lohmann、Max A. Syfrig、Masaaki Yoshifuji

  DOI：10.1016/s0040-4020(01)91914-3

  日期：1983.1
• Scully, Frank E.; Schlager, John J., Heterocycles, 1982, vol. 19, # 4, p. 653 - 656
  作者：Scully, Frank E.、Schlager, John J.

  DOI：——

  日期：——
• SCULLY, F. E. ,, JR;SCHLAGER, J. J., HETEROCYCLES, 1982, 19, N 4, 653-656
  作者：SCULLY, F. E. ,, JR、SCHLAGER, J. J.

  DOI：——

  日期：——