2-cinnamyl-1,2,3,4-tetrahydroisoquinoline | 145474-49-3

• 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: 2-cinnamyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-trans-cinnamyl-1,2,3,4-tetrahydro-isoquinoline；2-trans-Cinnamyl-1,2,3,4-tetrahydro-isochinolin；2-[(E)-3-phenylprop-2-enyl]-3,4-dihydro-1H-isoquinoline
• CAS: 145474-49-3
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: NGTBVPMVXAYHJZ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-cinnamyl-1,2,3,4-tetrahydroisoquinoline 在 silver carbonate 作用下， 以 xylene 为溶剂， 反应 18.0h， 以57%的产率得到1-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline
  参考文献：
  名称：

  XYZH systems as potential 1,3-dipoles. Part 36. 1,5-Electrocyclisation processes via oxidation of tertiary amines. Pyrrolo-dihydroisoquinolines and -dihydro-β-carbolines.

  摘要：

  A range of tertiary N-allylamines derived from 1,2,3,4-tetrahydroisoquinoline undergo oxidative cyclisation, induced by Ag2CO3, to pyrrolo-dihydroisoquinolines in moderate to good yield. Analogous oxidative cyclisations are reported for N-allyl-tetrahydro-beta-carbolines and a pyrrolidine. The reactions proceed via formation of a 1,5-dipole followed by an electrocyclisation and subsequent aromatisation.

  DOI：

  10.1016/s0040-4020(01)81190-x
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溶剂黄146 、 锌 作用下， 生成 2-cinnamyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  DE726008

  摘要：

  公开号：

文献信息

• Deammoniative Condensation of Primary Allylic Amines with Nonallylic Amines
  作者：Yong Wang、Manbo Li、Xiantao Ma、Congrong Liu、Yonghong Gu、Shi-Kai Tian

  DOI：10.1002/cjoc.201400406

  日期：2014.8

  through CN bond cleavage. In the presence of 5 mol% palladium diacetate, 10 mol% 1,4‐bis(diphenylphosphino)butane (dppb), and 5 mol% p‐toluenesulfonic acid (TsOH), a range of α‐unbranched primary allylic amines smoothly underwent deammoniative condensation with nonallylic amines in an α‐selective fashion to give structurally diverse secondary and tertiary amines in good to excellent yields and E selectivity

  与nonallylic胺伯烯丙基胺类空前deammoniative缩合反应已经通过C语言开发 N键裂解。在存在5 mol％的二乙酸钯，10 mol％的1,4-双（二苯基膦基）丁烷（dppb）和5 mol％的对甲苯磺酸（TsOH）的情况下，一系列α支链的伯烯丙基胺顺利进行了脱氨反应与非烯丙基胺以α选择性方式缩合，得到结构多样的仲胺和叔胺，并具有优异的产率和E选择性。用外消旋的2,2'-双（二苯基膦基）-1,1'-联萘（BINAP）代替dppb可以使对映体富集的α脱氨缩合手性伯烯丙基胺与非烯丙基胺，以完全保留构型。反应混合物的电喷雾电离（ESI）质谱分析可以鉴定一些π-烯丙基钯中间体，并且提出了可能的机理来解释脱氨缩合反应的区域选择性和立体选择性。
• Structure-Activity Relationship Studies of CNS Agents, Part 23[1]):N-(3-Phenylpropyl)- andN-[3(E)-Cinnamyl]-1,2,3,4-tetrahydroisoquinoline Mimic 1-Phenylpiperazine at 5-HT1A Receptors
  作者：Jerzy L. Mokrosz、Andrzej J. Bojarski、Sijka Charakchieva-Minol、Beata Duszynska、Maria J. Mokrosz、Maria H. Paluchowska

  DOI：10.1002/ardp.19953280707

  日期：——

  modelling studies it was also demonstrated that 6c, 6d and 8a mimicked very well the reference structures of 4a and its rigid analog 5. Another, more complex 1,2,3,4‐tetrahydroisoquinoline derivative 3, which served as a model compound to confirm the previously reported 5‐HT1A binding mode of derivatives 1a–d and 2, had the highest 5‐HT1A affinity (Ki = 6.7 ± 0.5 nM) of all the investigated compounds

  一组 1-芳基哌嗪 (4) 1,2,3,4-四氢异喹啉 (6) 和 - 喹啉 (7) 的 5-HT1A 受体亲和力和电离常数，含有 N-(ω-芳烷基) 或 N-( E) 确定了肉桂基取代基以及两种吗啉衍生物 (8a, 8b)。结果表明，一些四氢异喹啉 (6c, 6d) 和吗啉 (8a) 衍生物是 5-HT1A 配体等电位的 1-苯基哌嗪 (4a) 和 1,2,3,4,4a5-六氢吡嗪并 [1,2-a] 吲哚 ( 5）。在分子模型研究的基础上，还证明 6c、6d 和 8a 很好地模拟了 4a 及其刚性类似物 5 的参考结构。 另一种更复杂的 1,2,3,4-四氢异喹啉衍生物 3，用作用于确认先前报道的衍生物 1a-d 和 2 的 5-HT1A 结合模式的模型化合物具有最高的 5-HT1A 亲和力（Ki = 6.7 ± 0.
• A Novel Cleavage Technique To Generate Small Molecule Compounds and Libraries via a Two-Resin System
  作者：Xiaohu Ouyang、Robert W. Armstrong、Martin M. Murphy

  DOI：10.1021/jo971347w

  日期：1998.2.1

  Application of organic synthesis to solid supports has led to the successful implementation of combinatorial chemistry in the drug discovery process. This paper describes a novel use of the Hofmann elimination of tetrasubstituted amine salts on solid-phase resin to generate diverse combinatorial libraries of trisubstituted amines. Highly pure compounds were isolated without further purification by the addition of a second resin as the source reagent to promote the required elimination. The use of mixed resin systems to generate compounds is a novel application of bead-based technologies.
• Achieving Control over the Branched/Linear Selectivity in Palladium-Catalyzed Allylic Amination
  作者：Igor Dubovyk、Iain D. G. Watson、Andrei K. Yudin

  DOI：10.1021/jo3025253

  日期：2013.2.15

  Palladium-catalyzed reaction of unsymmetrical allylic electrophiles with amines gives rise to regioisomeric allylic amines. We have found that linear products result from the thermodynamically controlled isomerization of the initially formed branched products. The isomerization is promoted by protic acid and active palladium catalyst. The use of base shuts down the isomerization pathway and allows for the preparation and isolation of branched allylic amines. Solvent plays a key role in achieving high kinetic regioselectivity and in controlling the rate of isomerization. The isomerization can be combined with ring-closing metathesis to afford the synthesis of exocyclic allylic amines from their endocyclic precursors.
• DE725535
  申请人：——

  公开号：——

  公开（公告）日：——