2-(4-羟基-1H-吲哚-3-基)乙腈 | 118573-52-7

• 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
• 中文名称: 2-(4-羟基-1H-吲哚-3-基)乙腈
• 英文名称: 4-hydroxyindole-3-acetonirile
• 英文别名: indole-3-acetonitrile；2-(4-hydroxy-1H-indol-3-yl)acetonitrile
• CAS: 118573-52-7
• 化学式: C₁₀H₈N₂O
• 分子量: 172.186
• InChiKey: RWBSUCOEZMIDSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-羟基-1H-吲哚-3-基)乙腈 在 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 1-acetyl-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)indole-3-acetonitrile
  参考文献：
  名称：

  The First and Simple Total Synthesis of Cappariloside A

  摘要：

  A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3-acetonitrile with 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide was developed. Utilizing the method, the first and five steps total synthesis of cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yield.

  DOI：

  10.3987/com-00-8908
• 作为产物：
  描述：

  4-苄氧基吲哚-3-乙腈 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 以80 %的产率得到2-(4-羟基-1H-吲哚-3-基)乙腈
  参考文献：
  名称：

  铜催化C-S键偶联反应合成硫代吲哚的方法

  摘要：

  我们在此报道了铜催化吲哚与N-硫代琥珀酰亚胺的C-S键偶联反应，产生中等至优异的单磺酰化和双磺酰化化合物，如芳硫基吲哚、烷硫基吲哚、硒化吲哚和半胱氨酸取代的吲哚。板蓝根中吲哚生物碱C2位的硫代芳基化和硫代糖基化是通过结构修饰实现的。靛蓝靛甙III和IV的首次全合成已成功进行。原位产生的亲电子次磺基溴在催化循环中发挥重要作用。

  DOI：

  10.1021/acs.joc.3c02008

文献信息

• Compositions and methods for improving skin health and for the treatment and prevention of diseases, disorders and conditions associated with pathogenic microbes
  申请人：DermBiont, Inc.

  公开号：US11040077B2

  公开（公告）日：2021-06-22

  Disclosed herein are compositions and methods for using human-derived Janthinobacterium lividum. Compositions improve skin health. Methods may include applying human-derived Janthinobacterium lividum over a host or host area, such as skin or mucosa, to minimize the presence of one or more microbes, maximize therapeutic effects, and/or improve health. A method to minimize a pathogenic microbe may include applying to a surface a composition including human-derived Janthinobacterium lividum and an acceptable carrier. Compositions and methods may include a prebiotic to maximize growth and/or metabolites. Compositions and methods may include human-derived Janthinobacterium lividum metabolites, such as violacein, prodigiosin, indole-3-carboxaldehyde, and lantibiotics, and/or other Postbiotics.

  本文公开了使用源自人类的 Lividum Janthinobacterium 的组合物和方法。组合物可改善皮肤健康。方法可包括在宿主或宿主区域（如皮肤或粘膜）上施用源于人的生发的Lividum Janthinobacterium，以最大限度地减少一种或多种微生物的存在，最大限度地提高治疗效果，和/或改善健康状况。减少病原微生物的方法可包括向表面施用一种组合物，该组合物包括来源于人类的Janthinobacterium lividum和一种可接受的载体。组合物和方法可包括益生元，以最大限度地提高生长和/或代谢物。组合物和方法可包括来源于人的猪蓝细菌代谢物，如violacein、prodigiosin、吲哚-3-甲醛、兰特益生菌和/或其他后益生菌。
• COMPOSITIONS AND METHODS FOR IMPROVING SKIN HEALTH AND FOR THE TREATMENT AND PREVENTION OF DISEASES, DISORDERS AND CONDITIONS ASSOCIATED WITH PATHOGENIC MICROBES
  申请人：DermBiont, Inc.

  公开号：US20200345799A1

  公开（公告）日：2020-11-05

  Disclosed herein are compositions and methods for using human-derived Janthinobacterium lividum . Compositions improve skin health. Methods may include applying human-derived Janthinobacterium lividum over a host or host area, such as skin or mucosa, to minimize the presence of one or more microbes, maximize therapeutic effects, and/or improve health. A method to minimize a pathogenic microbe may include applying to a surface a composition including human-derived Janthinobacterium lividum and an acceptable carrier. Compositions and methods may include a prebiotic to maximize growth and/or metabolites. Compositions and methods may include human-derived Janthinobacterium lividum metabolites, such as violacein, prodigiosin, indole-3-carboxaldehyde, and lantibiotics, and/or other Postbiotics.
• The First and Simple Total Synthesis of Cappariloside A
  作者：Masanori Somei、Fumio Yamada

  DOI：10.3987/com-00-8908

  日期：——

  A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3-acetonitrile with 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide was developed. Utilizing the method, the first and five steps total synthesis of cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yield.
• A Method for the Synthesis of Thioindoles through Copper-Catalyzed C–S Bond Coupling Reaction
  作者：Jie Huang、Jin-Quan Li、Xin-Yue Cui、Yi-Han Qin、Shi-Jie Ma、Zi-An An、Wen-Wu Sun、Bin Wu

  DOI：10.1021/acs.joc.3c02008

  日期：2024.1.5

  We herein report the copper-catalyzed C–S bond coupling reaction of indoles with N-thiosuccinimides, resulting in moderate to excellent yields of mono- and bis-sulfenylated compounds such as arylthioindoles, alkylthioindoles, selenylated indoles, and cysteine-substituted indoles. Thioarylation and thioglycosylation at the C2 position of indole alkaloids in the Radix Isatidis were achieved via structural

  我们在此报道了铜催化吲哚与N-硫代琥珀酰亚胺的C-S键偶联反应，产生中等至优异的单磺酰化和双磺酰化化合物，如芳硫基吲哚、烷硫基吲哚、硒化吲哚和半胱氨酸取代的吲哚。板蓝根中吲哚生物碱C2位的硫代芳基化和硫代糖基化是通过结构修饰实现的。靛蓝靛甙III和IV的首次全合成已成功进行。原位产生的亲电子次磺基溴在催化循环中发挥重要作用。