1-allyl-2-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline | 132921-87-0

• 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-allyl-2-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: methyl 1-allyl-3,4-dihydroisoquinoline-2(1H)-carboxylate；methyl 1-prop-2-enyl-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 132921-87-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: GTNNVVBUOQWUDM-UHFFFAOYSA-N

物化性质

• 沸点：
  336.5±31.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(methoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline 在 tris(triphenylphosphine)ruthenium(II) chloride 四氯化钛 作用下， 以 苯 为溶剂， 反应 4.08h， 生成 1-allyl-2-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Novel method for α-substitution of amines via N-Methoxycarbonyl-α-t-butyldioxyamines

  摘要：

  alpha-Substitution of amines can be performed by ruthenium-catalyzed oxidation of N-methoxycarbonylamines with t-butyl hydroperoxide followed by treatment with nucleophiles in the presence of titanium tetrachloride.

  DOI：

  10.1016/s0040-4039(00)88520-2

文献信息

• Zinc Triflate as Lewis Acid in Nucleophilic Addition to Cyclic<i>N</i>-Acyliminium Ions
  作者：Ronaldo Aloise Pilli、Luís Gustavo Robello

  DOI：10.1055/s-2005-872659

  日期：——

  Zinc triflate-mediated nucleophilic addition of allytrimethylsilane, silyl enol ethers and terminal acetylenes to cyclic N-acyliminium ions at room temperature in CH 2 Cl 2 is described. The corresponding α-substituted heterocycles were obtained in moderate to good yields. The versatility of this reagent was demonstrated in the one-pot generation of the N-acyliminium ion and the zinc alkynylide species

  描述了在室温下在 CH 2 Cl 2 中，三氟甲磺酸锌介导的烯丙基三甲基硅烷、甲硅烷基烯醇醚和末端乙炔与环状 N-酰基胺离子的亲核加成。以中等至良好的产率获得了相应的 α-取代杂环。该试剂的多功能性在 N-acyliminium 离子和炔基锌物质的一锅生成中得到证明，然后通过它们的偶联反应以中等产率提供炔丙基加合物。
• Direct C–H Allylation of <i>N</i>-Acyl/Sulfonyl Tetrahydroisoquinolines and Analogues
  作者：Changcun Yan、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.5b03042

  日期：2015.11.20

  A highly efficient direct C–H allylation reaction at the α position of N-acyl/sulfonyl tetrahydroisoquinolines under mild conditions was developed. The reaction was also suitable for allylation of other protected nitrogen-containing heterocycles. Several interesting transformations of the products into valuable synthetic intermediates are featured with the successful total synthesis of (±)-crispine

  在温和条件下，开发了在N-酰基/磺酰基四氢异喹啉的α位上高效的直接CH烯丙基化反应。该反应也适合于其他保护的含氮杂环的烯丙基化。（±）-crispine A的成功全合成成功地将产品有趣地转化为有价值的合成中间体。
• “Cation Flow” Method:  A New Approach to Conventional and Combinatorial Organic Syntheses Using Electrochemical Microflow Systems
  作者：Seiji Suga、Masayuki Okajima、Kazuyuki Fujiwara、Jun-ichi Yoshida

  DOI：10.1021/ja015823i

  日期：2001.8.1
• Addition of activated olefins to cyclic N-acyliminium ions in ionic liquids
  作者：Ronaldo Aloise Pilli、Luís Gustavo Robello、Nilton Soares Camilo、Jairton Dupont、Alexandre Augusto Moreira Lapis、Brenno A. da Silveira Neto

  DOI：10.1016/j.tetlet.2005.12.102

  日期：2006.3

  Organoindate(III) ionic liquid ((BMIInCl4)-In-.) was successfully employed in the nucleophilic addition of allyltrimethylsilane, silyl enol ethers and ketene silyl acetals to in situ generated cyclic N-acyliminium ions at room temperature without the need of an external Lewis acid. The corresponding alpha-substituted heterocycles were obtained in good yields and the recovered ionic liquid phase could be reused at least three times. (c) 2006 Elsevier Ltd. All rights reserved.
• NAOTA, TAKESHI;NAKATO, TAKESHI;MURAHASHI, SHUN-ICHI, TETRAHEDROM LETT., 31,(1990) N1, C. 7475-7478
  作者：NAOTA, TAKESHI、NAKATO, TAKESHI、MURAHASHI, SHUN-ICHI

  DOI：——

  日期：——