1-trifluoroacetyl-1,2,3,8-tetrahydropyrrolo[2,3-b]indole

• 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-trifluoroacetyl-1,2,3,8-tetrahydropyrrolo[2,3-b]indole
• 英文别名: 1-(2,4-dihydro-1H-pyrrolo[2,3-b]indol-3-yl)-2,2,2-trifluoroethanone
• 化学式: C₁₂H₉F₃N₂O
• 分子量: 254.211
• InChiKey: UAODJJUXCDHRGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-hydroxy-Nb-trifluoroacetyltryptamine 在 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以8%的产率得到6-mesyloxy-Nb-trifluoroacetyltryptamine
  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

文献信息

• 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
• 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.
• Novel Formations of 6-Mesyloxytryptamines and 1-Substituted 3a-(4-Chlorobutoxy)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles in the Reaction of Nb-Substituted 1-Hydroxytryptamines with Mesyl Chloride
  作者：Masanori Somei、Masakazu Hasegawa、Yoshiyuki Nagahama、Kensuke Kobayashi、Masumi Hayashi

  DOI：10.3987/com-99-s44

  日期：——
• Yamada, Fumio; Goto, Aya; Somei, Masanori, Heterocycles, 2000, vol. 53, # 6, p. 1255 - 1258
  作者：Yamada, Fumio、Goto, Aya、Somei, Masanori

  DOI：——

  日期：——
• The Chemistry of 1-Hydroxyindole Derivatives: Nucleophilic Substitution Reactions on Indole Nucleus
  作者：Masanori Somei、Toshiya Kawasaki、Yoshikazu Fukui、Fumio Yamada、Tetsuya Kobayashi、Harumi Aoyama、Daisuke Shinmyo

  DOI：10.3987/com-92-6140

  日期：——

  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.