2,3-dihydro-N,N-dimethyltryptamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3-dihydro-N,N-dimethyltryptamine
• 英文别名: 2-(indolin-3-yl)-N,N-dimethylethanamine；2-(dihydroindol-3-yl)-N,N-dimethylethylamine；[2-(2,3-dihydro-indol-3-yl)-ethyl]-dimethyl-amine；2-(2,3-dihydro-1H-indol-3-yl)-N,N-dimethylethanamine
• 化学式: C₁₂H₁₈N₂
• 分子量: 190.288
• InChiKey: QJONJVMVPXLFKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-N,N-dimethyltryptamine 在 硫酸 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.0h， 生成 利扎曲坦
  参考文献：
  名称：

  一种制备苯甲酸利扎曲坦的方法

  摘要：

  本发明公开了一种新的苯甲酸利扎曲坦的制备方法。该制备方法以色胺为起始原料，经过N，N甲基化，还原，上保护、三氮唑甲基化、脱保护、脱氢，成盐七步反应，得到高纯度的苯甲酸利扎曲坦。该方法的创新之处在于采用了一种全新的方法构建吲哚环，避免了现有路线中使用的fisher吲哚合成法而带来的产品杂质含量高，难于纯化的缺点。该方法的优点为：操作简便，反应条件温和，无昂贵试剂，不需要柱层析纯化，产品纯度高。

  公开号：

  CN103664900B
• 作为产物：
  描述：

  N,N-二甲基色胺 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 2.0h， 以93%的产率得到2,3-dihydro-N,N-dimethyltryptamine
  参考文献：
  名称：

  The Chemistry of Indoles. CIII. Simple Syntheses of Serotonin, N-Methylserotonin, Bufotenine, 5-Methoxy-N-methyltryptamine, Bufobutanoic Acid, N-(Indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and Lespedamine Based on 1-Hydroxyindole Chemistry.

  摘要：

  本文描述了利用1-羟色胺的选择性亲核取代反应，合成新型简单物质的方法，这些物质包括：血清素（1a）、N-甲基血清素（1b）、蟾毒色胺（1c）、5-甲氧基-N-甲基色胺（2a）、蟾毒色酸（3a）、N-(吲哚-3-基)甲基-5-甲氧基-N-甲基色胺（4）和莱斯佩达明（5）。此外，还报道了有效的5-苄氧基色胺和1-甲氧基-2-氧吲哚合成方法。

  DOI：

  10.1248/cpb.49.87

文献信息

• Asymmetric<i>N</i>-Allylation of Indoles Through the Iridium-Catalyzed Allylic Alkylation/Oxidation of Indolines
  作者：Wen-Bo Liu、Xiao Zhang、Li-Xin Dai、Shu-Li You

  DOI：10.1002/anie.201200649

  日期：2012.5.21

  N‐allylindoles by a one‐pot Ir‐catalyzed asymmetric allylic alkylation/oxidation reaction of indolines has been realized. The current method features high regioselectivity and enantioselectivity together with a broad range of indoles with varying electronic properties. The utility of this method was demonstrated by the synthesis of dihydropyrrolo[1,2‐a]indole derivatives.

  有两个步骤可能比一个步骤更好：通过一锅Ir催化的二氢吲哚的不对称烯丙基烷基化/氧化反应，可以有效地合成对映体富集的N-烯丙基。目前的方法具有很高的区域选择性和对映选择性，以及范围广泛的具有不同电子特性的吲哚。通过合成二氢吡咯并[1,2- a ]吲哚衍生物证明了该方法的实用性。
• A novel and convenient route for the construction of 5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indoles and its application in the synthesis of Rizatriptan
  作者：Yi He、Xiaolong Li、Jue Li、Xiaocen Li、Li Guo、Li Hai、Yong Wu

  DOI：10.1016/j.tetlet.2014.05.063

  日期：2014.7

  In this study, a novel and convenient route for the construction of 5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indoles (8) is presented starting from (1H-1,2,4-triazol-1-yl)methanol (5) and indolines (6) under 98% H2SO4 at room temperature for 4-24 h, followed by deacetylation and dehydrogenation. Based on this finding, a novel route to synthesize Rizatriptan starting from tryptamine was designed and accomplished with 48.5% overall yield in 6 steps. Compared with operational art, the new route afforded higher yield and more pure products requiring no chromatographic purification, which may further be applied in industrialization. (C) 2014 Elsevier Ltd. All rights reserved.
• Somei, Masanori; Yamada, Fumio; Morikawa, Harunobu, Heterocycles, 1997, vol. 46, p. 91 - 94
  作者：Somei, Masanori、Yamada, Fumio、Morikawa, Harunobu

  DOI：——

  日期：——
• Simple Syntheses of Lespedamine and 5-Bromo-N,N-dimethyltryptamine Based on 1-Hydroxyindole Chemistry
  作者：Masanori Somei、Kensuke Kobayashi、Keiko Tanii、Toshihiko Mochizuki、Yumiko Kawada、Yashikazu Fukui

  DOI：10.3987/com-94-s26

  日期：——

  Various types of 1-hydroxyindoles were prepared for the first time. Through methylation or acid catalyzed nucleophilic bromination of N,N-dimethyl-1-hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.
• 2,3-Dihydro and carbocyclic analogs of tryptamines: interaction with serotonin receptors
  作者：Richard A. Glennon、John M. Jacyno、John J. Salley

  DOI：10.1021/jm00343a013

  日期：1982.1

  Several dihydro and carbocyclic analogues of tryptamine were evaluated in order to determine the role of the heterocyclic portion of the indole nucleus on the interaction of indolealkylamines with the serotonin receptors of the rat fundus. Reduction of the C2--C3 double bond or replacement of the indole nitrogen with an sp3-hybridized carbon atom results in a 50% decrease in receptor affinity. Complete removal of the five-membered ring of N,N-dimethyltryptamine reduces affinity by an order of magnitude. It appears that an intact indole nucleus, though not entirely necessary, results in an optimal receptor interaction for the indolealkylamines examined.