1-羟基吲哚-3-甲醛 | 67282-51-3

• 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
• 中文名称: 1-羟基吲哚-3-甲醛
• 英文名称: 1-hydroxy-1H-indole-3-carbaldehyde
• 英文别名: 1-hydroxyindole-3-carboxaldehyde；1-hydroxyindole-3-carbaldehyde；N-hydroxyindole-3-carbaldehyde；1-hydroxy-indole-3-carbaldehyde；1-Hydroxyindol-3-carbaldehyd
• CAS: 67282-51-3
• 化学式: C₉H₇NO₂
• 分子量: 161.16
• InChiKey: OGICCHVXAZFEQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-羟基吲哚-3-甲醛 、 N,N'-二环己基碳二亚胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到N,N'-dicyclohexyl-N-(3-formylindol-2-yl)urea
  参考文献：
  名称：

  Kawasaki, Toshiya; Kodama, Atsushi; Nishida, Tokiko, Heterocycles, 1991, vol. 32, # 2, p. 221 - 227

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[2-(三甲基甲硅烷基)乙氧基]-吲哚 在 三氟化硼乙醚 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 1-羟基吲哚-3-甲醛
  参考文献：
  名称：

  A New Synthesis of 1-Hydroxyindoles and Spectra of 1-Hydroxyindole

  摘要：

  DOI：

  10.3987/com-95-s2

文献信息

• A General Synthesis of <i>N</i>-Hydroxyindoles
  作者：Audrey Wong、Jeffrey T. Kuethe、Ian W. Davies

  DOI：10.1021/jo035351l

  日期：2003.12.1

  A general method for the formation of N-hydroxyindoles is demonstrated through a lead-promoted intramolecular reductive cyclization of o-nitrobenzyl ketones and aldehydes under transfer hydrogenation conditions. The N-hydroxyindoles are isolated in high purity and excellent yield (>90%) in an operationally simple procedure. This new method is exemplified by a two-step synthesis of the naturally occurring

  N-羟基吲哚形成的一般方法通过转移氢化条件下的邻硝基苄基酮和醛的铅促进的分子内还原环化来证明。N-羟基吲哚在操作简单的过程中以高纯度和优异的收率（> 90％）分离。这种新方法以天然存在的1-甲氧基吲哚-3-甲醛的两步合成为例，这在许多生物碱总合成中至关重要。
• A New General Synthesis of <i>N</i>-Hydroxyindoles
  作者：Michel Belley、Daniel Beaudoin、Gabriel St-Pierre

  DOI：10.1055/s-2007-990970

  日期：2007.12

  Catalytic hydrogenation of 2-nitrobenzyl aldehydes, ketones and amides, using Pd/C and (Ph 3 P) 4 Pd, affords N-hydroxyin-doles in good to excellent overall yields.

  使用 Pd/C 和 (Ph 3 P) 4 Pd 对 2-硝基苄醛、酮和酰胺进行催化加氢，以良好至优异的总产率提供 N-羟基吲哚。
• Use of indole compounds for fat reduction and skin and soft tissue tightening
  申请人：Alevere Medical Corporation

  公开号：US10258605B2

  公开（公告）日：2019-04-16

  The present invention relates to indole compounds and compositions and uses thereof, including uses of the indole compounds and compositions for the reduction or removal of localized fat deposits and/or tightening of skin and soft tissue laxity in subjects. The indole compounds can be employed, for example, in the cosmetic sector or for producing pharmaceutical products.

  本发明涉及吲哚化合物和组合物及其用途，包括吲哚化合物和组合物用于减少或去除局部脂肪沉积和/或收紧受试者的皮肤和软组织松弛。例如，吲哚化合物可用于化妆品行业或生产医药产品。
• 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.
• Creation of New Promoters for Plant’s Root Growth: Its Application for the Syntheses of Vulcanine and Borreline, and for Combating Desertification at Gobi Desert in Inner Mongolia
  作者：Masanori Somei、Shinsuke Sayama、Katsumi Naka、Kotaro Shinmoto、Fumio Yamada

  DOI：10.3987/com-07-s(u)31

  日期：——

  Various new 2-substituted indole-3-carbaldehydes are prepared. Structurally related alkaloids, vulcanine and borreline, are synthesized as well. Among the compounds, 2-haloindole-3-carbaldehydes are found to be potent promoters of plant's root growth. Its successful preliminary application is reported for making Gobi desert in Inner Mongolia full of plant.