1-hydroxy-Nb-trifluoroacetyltryptamine | 180910-54-7

• 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: 1-hydroxy-Nb-trifluoroacetyltryptamine
• 英文别名: Nb-trifluoroacetyl-1-hydroxytryptamine；2,2,2-trifluoro-N-[2-(1-hydroxyindol-3-yl)ethyl]acetamide
• CAS: 180910-54-7
• 化学式: C₁₂H₁₁F₃N₂O₂
• 分子量: 272.227
• InChiKey: SPXNMANDQZTTDJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxy-Nb-trifluoroacetyltryptamine 在 sodium hydride 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-acetyl-6-mesyloxy-Nb-trifluoroacetyltriptamine
  参考文献：
  名称：

  The Chemistry of 1-Hydroxyindole Derivatives: Nucleophilic Substitution Reactions on Indole Nucleus

  摘要：

  Nucleophilic substitution reactions were newly found to occur generally in the chemistry of 1-hydroxyindole derivatives. Its application to the synthesis of a phytoalexin, brassicanal A, is reported.

  DOI：

  10.3987/com-92-6140
• 作为产物：
  描述：

  N-[2-(2,3-Dihydro-1H-indol-3-yl)-ethyl]-2,2,2-trifluoro-acetamide 在 sodium tungstate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 以72%的产率得到1-hydroxy-Nb-trifluoroacetyltryptamine
  参考文献：
  名称：

  Simple Syntheses of Lespedamine and 5-Bromo-N,N-dimethyltryptamine Based on 1-Hydroxyindole Chemistry

  摘要：

  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.

  DOI：

  10.3987/com-94-s26

文献信息

• Nucleophilic Substitution Reaction on the Nitrogen of Indole Nucleus: A Novel Synthesis of 1-Aryltryptamines
  作者：Masanori Somei、Toshikatsu Hayashi、Wu Peng、Yu-ya Nakai、Koji Yamada

  DOI：10.3987/com-01-9417

  日期：——

  1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nitrogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles, 5- and 7-substituted tryptamines can also be produced in addition to the 1-aryltryptamines.

  1-羟基色胺衍生物通过酸处理作为一般反应在吲哚氮（Na）上发生亲核取代反应，为1-芳基色胺的合成提供了一种新方法。根据亲核试剂的结构，除了 1-芳基色胺之外，还可以产生 5-和 7-取代的色胺。
• Nucleophilic Substitution Reactions on Indole Nucleus: Formation of (3a,8a-cis)-1,2,3,3a,8,8a-Hexahydropyrrolo[2,3-b]indoles Having a Substituent at the 3a-Position
  作者：Masanori Somei、Fumio Yamada、Aya Goto、Masakazu Hasegawa、Kensuke Kobayashi

  DOI：10.3987/com-16-s(s)53

  日期：——

  ictly determined. INTRODUCTION We have opened the door to the chemistry of 1-hydro xyindole and 1-hydroxytryptophan derivatives, 3 and demonstrated that these compounds generally undergo nucleophilic substitution reaction, 4 which was thus far rarely observed in indole chemistry. 4 In our 1-hydroxyindole hypothesis, 5 we assume the 1-hydroxy group of the general formu la (A) in Scheme 1 departs, after

  各种亲核试剂，如吲哚、1,2,3-三乙氧基苯、苯甲醚、苯酚和吡咯，在甲磺酰氯存在下与1-羟基-Nb-三氟乙酰色胺反应生成新的(3a,8acis)系列-1,2,3,3a,8,8a-六氢吡咯并[2,3b]吲哚在3a位有一个取代基。它们的结构和副产品是严格确定的。引言 我们打开了 1-羟基吲哚和 1-羟基色氨酸衍生物 3 化学的大门，并证明这些化合物通常会发生亲核取代反应 4，这在吲哚化学中迄今为止很少观察到。4 在我们的 1-羟基吲哚假设中，5 我们假设方案 1 中通式 (A) 的 1-羟基基团在转化为良好的离去基团 (B) 后离开，留下共振稳定的吲哚基阳离子 (C) . 可以用合适的亲核试剂捕获它，得到亚胺 6 (D)。# 献给 M asakatsu Shibasaki NHR 教授 70 岁生日
• Yamada, Fumio; Goto, Aya; Peng, Wu, Heterocycles, 2003, vol. 61, p. 163 - 172
  作者：Yamada, Fumio、Goto, Aya、Peng, Wu、Hayashi, Toshikatsu、Saga, Yoshitomo、Somei, Masanori

  DOI：——

  日期：——
• Nucleophilic Substitution Reaction on the Nitrogen of Indole Nucleus: Formation of 1-(Indol-3-yl)indoles upon Reaction of 1-Hydroxyindoles with Indole in Formic Acid
  作者：Masanori Somei、Fumio Yamada、Toshikatsu Hayashi、Aya Goto、Yoshitomo Saga

  DOI：10.3987/com-00-9135

  日期：——

  1-(Indol-3-yl)indoles are obtained in excellent to good yields by the reaction of 1-hydroxyindoles with indole in 85% formic acid. Their structures are determined by X-Ray crystallographic analysis and chemical correlations. The unprecidented SN2 mechanism on the indole nitrogen is proposed.
• Reactions of 1-Hydroxyindoles with p-Toluenesulfonyl Chloride and p-Toluenesulfonic Acid
  作者：Masanori Somei、Fumio Yamada、Aya Goto、Masumi Hayashi、Masakazu Hasegawa

  DOI：10.3987/com-00-9038

  日期：——

  1-Hydroxyindoles produced novel types of compounds such as 4-substituted indoles and 4H-1, 3-dioxolo[4,5-b]indoles upon reaction with p-toluenesulfonyl chloride in acetone. Contrastively, 5-tosyloxyindole and 2H-1,2-oxazino[2, 3-a]indole were generated upon reaction with p-toluenesulfonic acid in acetone.