5-甲氧基-1H-吲哚-3-乙醇 3-乙酸酯 | 6127-51-1

• 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: 5-甲氧基-1H-吲哚-3-乙醇 3-乙酸酯
• 中文别名: 5-甲氧基-1H-吲哚-3-乙醇3-乙酸酯
• 英文名称: O-Acetyl-5-methoxytryptophol
• 英文别名: 2-(5-methoxy-1H-indol-3-yl)ethyl acetate；1-acetoxy-2-(5-methoxy-indol-3-yl)-ethane；3-(2-Acetoxyethyl)-5-methoxyindole；3-(2-Acetoxyethyl)-5-methoxyindol
• CAS: 6127-51-1
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: HVYLYRVBNPNNMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-甲氧基-1H-吲哚-3-乙醇 3-乙酸酯 在 4-二甲氨基吡啶 、 potassium carbonate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 43.5h， 生成 6,5′-dimethyl hyrtiosulawesine
  参考文献：
  名称：

  Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities

  摘要：

  A series of 1-indolyl substituted beta-carbolines including the natural products hyrtiosulawesine, pityriacitrin and pityriacitrin B were prepared via Pictet-Spengler condensation oxidation strategy from the corresponding indolyl-acetaldehydes and substituted tryptamines. Efforts to prepare the C-1 methylene-linked beta-carboline analogues for structure activity relationship studies were unsuccessful. Biological evaluation revealed two analogues (5 and 41) to exhibit weak inhibition of phospholipase A(2) (IC50 171 and 131 mu M, respectively), two to act as antioxidants (3 and 43), and 12 analogues with activity towards a chloroquine-resistant strain (FcB1) of Plasmodium falciparum (IC50 1.0-23 mu M). Testing against a panel of 60 human tumour cell lines revealed a general lack of cytotoxic effect for most of the compounds with the exception of beta-carboline 42 exhibiting modest antileukaemic activity towards the HL-60(TB) cell line (LC50 4.2 mu M). In addition, two novel structures (30 and 32) resulting from aldol condensation followed by Pictet-Spengler cyclisation displayed cytotoxicity with pronounced subpanel specificities towards colon cancer (COLO 205 and HCC-2998) cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.068
• 作为产物：
  描述：

  (5-甲氧基-1H-吲哚-3-基)(氧代)乙酰氯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 21.0h， 生成 5-甲氧基-1H-吲哚-3-乙醇 3-乙酸酯
  参考文献：
  名称：

  Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities

  摘要：

  A series of 1-indolyl substituted beta-carbolines including the natural products hyrtiosulawesine, pityriacitrin and pityriacitrin B were prepared via Pictet-Spengler condensation oxidation strategy from the corresponding indolyl-acetaldehydes and substituted tryptamines. Efforts to prepare the C-1 methylene-linked beta-carboline analogues for structure activity relationship studies were unsuccessful. Biological evaluation revealed two analogues (5 and 41) to exhibit weak inhibition of phospholipase A(2) (IC50 171 and 131 mu M, respectively), two to act as antioxidants (3 and 43), and 12 analogues with activity towards a chloroquine-resistant strain (FcB1) of Plasmodium falciparum (IC50 1.0-23 mu M). Testing against a panel of 60 human tumour cell lines revealed a general lack of cytotoxic effect for most of the compounds with the exception of beta-carboline 42 exhibiting modest antileukaemic activity towards the HL-60(TB) cell line (LC50 4.2 mu M). In addition, two novel structures (30 and 32) resulting from aldol condensation followed by Pictet-Spengler cyclisation displayed cytotoxicity with pronounced subpanel specificities towards colon cancer (COLO 205 and HCC-2998) cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.068

文献信息

• Silver(I)/Dirhodium(II) Catalytic Platform for Asymmetric N–H Insertion Reaction of Heteroaromatics
  作者：Shingo Harada、Shumpei Hirose、Mizuki Takamura、Maika Furutani、Yuna Hayashi、Tetsuhiro Nemoto

  DOI：10.1021/jacs.3c10596

  日期：2024.1.10

  platform. Although a previously developed catalysis comprising chiral silver catalyst or dirhodium(II,II) paddlewheel complexes with and without chiral phosphoric acid showed modest performance, a unique combination of widely available Rh2(OAc)4 and silver(I) phosphate dimer [(S)-TRIP-Ag]2 enabled asymmetric carbene insertion reactions (up to 98% ee). Moreover, the Ag/Rh catalytic system facilitated regioselective

  过渡金属催化的卡宾对映选择性 N-H 插入反应为生产手性含氮化合物提供了一种强大而直接的策略。使用吲哚变体开发高选择性插入反应可以满足合成需求。在此，我们提出了基于异核催化平台，使用供体/受体取代的重氮化合物向芳香杂环的 N-H 键进行不对称插入反应。尽管先前开发的包含手性银催化剂或二铑 (II,II) 叶轮络合物（含或不含手性磷酸）的催化剂表现出适度的性能，但广泛使用的 Rh 2 (OAc) 4和磷酸银 (I) 二聚体的独特组合 [( S )-TRIP-Ag] 2实现不对称卡宾插入反应（高达 98% ee）。此外，Ag/Rh催化系统促进了质子吲哚的区域选择性和对映选择性C-H功能化。基于密度泛函理论的机理研究表明，原位生成的银铑三金属烯醇化物在手性环境中被质子化。