N-nonanoyltryptamine | 21469-21-6

• 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: N-nonanoyltryptamine
• 英文别名: Nonanoyl tryptamine；N-[2-(1H-indol-3-yl)ethyl]nonanamide
• CAS: 21469-21-6
• 化学式: C₁₉H₂₈N₂O
• 分子量: 300.444
• InChiKey: JHKBQGYMCOBVJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-nonanoyltryptamine 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 0.5h， 以78%的产率得到2,3-dihydro-N(b)-nonanoyltryptamine
  参考文献：
  名称：

  Synthesis of Nb-Acyltryptamines and Their 1-Hydroxy-tryptamine Derivatives as New α2-Blockers

  摘要：

  N-b-Acyl- and N-b-acyl-1-hydroxytryptamines are found to be novel and structurally simple alpha(2)-blocker for the treatment of erectile dysfunction.

  DOI：

  10.3987/com-08-s(d)29
• 作为产物：
  描述：

  色胺 、 Methoxycarbonyl nonanoate 以 氯仿 为溶剂， 反应 0.5h， 以1.78 g的产率得到N-nonanoyltryptamine
  参考文献：
  名称：

  Synthesis of Nb-Acyltryptamines and Their 1-Hydroxy-tryptamine Derivatives as New α2-Blockers

  摘要：

  N-b-Acyl- and N-b-acyl-1-hydroxytryptamines are found to be novel and structurally simple alpha(2)-blocker for the treatment of erectile dysfunction.

  DOI：

  10.3987/com-08-s(d)29

文献信息

• Rh(I)-Catalyzed Hydroamidation of Olefins via Selective Activation of N–H Bonds in Aliphatic Amines
  作者：Kaiwu Dong、Xianjie Fang、Ralf Jackstell、Gabor Laurenczy、Yuehui Li、Matthias Beller

  DOI：10.1021/jacs.5b02218

  日期：2015.5.13

  Hydroamidation of olefins constitutes an ideal, atom-efficient method to prepare carboxylic amides from easily available olefins, CO, and amines. So far, aliphatic amines are not suitable for these transformations. Here, we present a ligand- and additive-free Rh(I) catalyst as solution to this problem. Various amides are obtained in good yields and excellent regioselectivities. Notably, chemoselective

  烯烃的加氢酰胺化是一种理想的、原子效率高的方法，可以从容易获得的烯烃、CO 和胺类制备羧酰胺。到目前为止，脂肪胺不适合这些转化。在这里，我们提出了一种不含配体和添加剂的 Rh(I) 催化剂来解决这个问题。以良好的产率和优异的区域选择性获得了各种酰胺。值得注意的是，脂肪胺的化学选择性酰胺化发生在芳香胺和醇的存在下。机理研究表明，Rh-酰基物质的存在是所提出的 Rh(I)-催化循环中选择性和限速步骤的关键中间体。
• First reported propylphosphonic anhydride (T3P®) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles
  作者：Tímea Szabó、András Dancsó、Péter Ábrányi-Balogh、Balázs Volk、Mátyás Milen

  DOI：10.1016/j.tetlet.2019.04.024

  日期：2019.5

  In the present work, a propylphosphonic anhydride (T3P®) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitrile under microwave irradiation, and the product isolation required only an extraction and subsequent crystallization; no chromatography was necessary. The desired

  在目前的工作中，丙基膦酸酐（T3P ®）辅助的罗宾逊-加布里埃尔环化Ñ酰基-β-oxotryptamines为2-取代-5-（3-吲哚基）恶唑已经开发的合成。在微波辐射下，反应在乙腈中顺利进行，产物的分离仅需萃取并随后结晶。无需层析。以良好至优异的产率获得了所需的产物。
• Method for reducing itching in atopic dermatitis
  申请人：Somei Masanori

  公开号：US11065229B2

  公开（公告）日：2021-07-20

  This invention relates to a method for treating atopic dermatitis, comprising administering an effective amount of N-acyltryptamine represented by Formula (I): wherein R represents a saturated aliphatic hydrocarbon group having 2 to 29 carbon atoms; or a pharmaceutically acceptable salt, hydrate or solvate thereof to a subject in need thereof.

  本发明涉及一种治疗特应性皮炎的方法，包括施用有效量的由式（I）代表的 N-酰色胺： 其中 R 代表具有 2 至 29 个碳原子的饱和脂肪族烃基；或其药学上可接受的盐、水合物或溶液。
• The Ideal Synthetic Method Aimed at the Leads for an a2-Blocker, an Inhibitor of Blood Platelet Aggregation, and an Anti-osteoporosis Agent
  作者：Masanori Somei、Takako Iwaki、Fumio Yamada、Yoshio Tanaka、Koki Shigenobu、Katsuo Koike、Nobuo Suzuki、Atsuhiko Hattori

  DOI：10.3987/com-06-10771

  日期：——

  According to the definition of the ideal synthetic method, an example aimed at the leads for an alpha(2)-blocker, an inhibitor of platelet aggregation, and an anti-osteoporosis agent is established starting from tryptamine. The originality rate, the intellectual property, and the application potential factors of the method are 71, 54, and 100, respectively. The method employs only conventional reagents and reaction conditions without using any protecting groups.
• Receptor Blocker and Vasodilator Comprising Indole Derivative as Active Ingredient
  申请人：Somei Masanori

  公开号：US20090005430A1

  公开（公告）日：2009-01-01

  It is intended to find a compound that is structurally simpler than yohimbine, a pentacyclic condensed heterocyclic compound, and has an effect similar to that of yohimbine. The present invention relates to a pharmaceutical or food composition for α 2 receptor blockage comprising a compound represented by the formula (I) or a pharmaceutically acceptable salt thereof: (wherein R 1 represents a hydrogen, alkyl group, alkenyl group, alkynyl group, aromatic group, aralkyl group, acyl group, arylsulfonyl group, alkylsulfonyl group, or hydroxyl group; R 2 represents a hydrocarbon group; R 3 , R 4 , R 5 , R 6 , and R 7 are the same or different and represent a hydrogen, halogen, alkyl group, or alkoxy group; R 8 represents a hydrogen or acyl group; n represents an integer of 1 to 6; and a and b are the same or different and represent 1 or 0).