tert-butyl 3-(2-oxoethyl)-1H-indole-1-carboxylate | 151696-51-4

• 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: tert-butyl 3-(2-oxoethyl)-1H-indole-1-carboxylate
• 英文别名: tert-butyl 3-(2-oxoethyl)indole-1-carboxylate
• CAS: 151696-51-4
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: FUYFVHMYRDRJMM-UHFFFAOYSA-N

物化性质

• 沸点：
  397.6±34.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2-oxoethyl)-1H-indole-1-carboxylate 在 potassium permanganate 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  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：

  甲基吲哚-3-乙酸盐 在 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 26.0h， 生成 tert-butyl 3-(2-oxoethyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  高效地合成天然二肽Jaspamide和Chondramide的肽片段

  摘要：

  可以通过Ugi反应合成生物碱jaspamide和chondramide的三肽部分。这种方法比以前报道的方法要短得多。

  DOI：

  10.1002/ejoc.201800992

文献信息

• [EN] HYDROXAMIC ACIDS USEFUL IN THE TREATMENT OF HYPER-PROLIFERATIVE DISORDERS<br/>[FR] ACIDES HYDROXAMIQUES UTILISES POUR TRAITER DES TROUBLES D'HYPERPROLIFERATION
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2004094376A1

  公开（公告）日：2004-11-04

  This invention relates to a compound of Formula (I) and its use in treating hyper-proliferative disorders.

  这项发明涉及一种式（I）化合物及其在治疗高增殖性疾病中的用途。
• Synthesis of Highly Functionalized Pyridines: A Metal-Free Cascade Process
  作者：Kai Wei、Yu-Cui Sun、Rui Li、Jing-Feng Zhao、Wen Chen、Hongbin Zhang

  DOI：10.1021/acs.orglett.1c02234

  日期：2021.9.3

  Herein, we report a new process for the synthesis of highly functionalized pyridines based on a tandem Pummerer-type rearrangement, aza-Prins cyclization, and elimination-induced aromatization. This formal [5+1] cyclization provides pyridines in good yields with easily accessible starting materials. The synthetic potential of our new method is further demonstrated in the modification of the frameworks

  在此，我们报告了一种基于串联 Pummerer 型重排、氮杂-Prins 环化和消除诱导的芳构化合成高度官能化吡啶的新工艺。这种正式的 [5+1] 环化以良好的收率提供了易于获得的起始材料的吡啶。我们新方法的合成潜力在 BINOL 和一些天然产物的框架的修改中得到了进一步证明。
• Stereospecific access to bridged [n.2.1] skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides
  作者：Tong-De Tan、Xin-Qi Zhu、Mei Jia、Yongjia Lin、Jun Cheng、Yuanzhi Xia、Long-Wu Ye

  DOI：10.1016/j.cclet.2019.10.019

  日期：2020.5

  cycloisomerization-initiated tandem reaction of Boc-protected indole tethered homopropargyl amides has been achieved. This method delivers a wide range of valuable bridged aza-[n.2.1] skeletons (n = 3–7) at room temperature with high diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the gold-catalyzed tandem reaction of homopropargyl alcohol is also achieved to produce

  摘要实现了由Boc保护的吲哚链式均炔丙基酰胺的高效金催化抗马氏复合环引发的串联反应。该方法可通过手性转移策略在室温下提供多种有价值的桥连氮杂[n.2.1]骨架（n = 3-7），具有高非对映选择性和对映选择性。此外，还实现了金炔丙醇的串联催化反应，以生产桥联的氧杂-[3.2.1]骨架。
• Organocatalytic Multicomponent Synthesis of α/β‐Dipeptide Derivatives
  作者：Thomas Martzel、Julien Annibaletto、Pierre Millet、Etienne Pair、Morgane Sanselme、Sylvain Oudeyer、Vincent Levacher、Jean‐François Brière

  DOI：10.1002/chem.202001214

  日期：2020.7.14

  multicomponent Knoevenagel‐aza‐Michael‐cyclocondensation reaction involving readily available hydroxamic acid‐derived from naturally occurring α‐amino acids allows a diversity‐oriented synthesis of novel isoxazolidin‐5‐ones possessing an N‐protected α‐amino acid pendant with good to high diastereoselectivities thanks to a match effect with a chiral organocatalyst. These diversely substituted heterocycles

  简单的多组分Knoevenagel-氮杂-Michael-环缩合反应涉及容易得的天然存在的α-氨基酸衍生的异羟肟酸，可实现具有N-保护的α-氨基酸侧基且具有良好保护作用的新型异恶唑烷5-5异构体的合成。与手性有机催化剂的匹配作用，使非对映选择性高。这些被不同取代的杂环很容易作为单个非对映异构体分离，被证明是形成一系列α/β-二肽片段的通用平台。
• Chichibabin pyridinium synthesis <i>via</i> oxidative decarboxylation of photoexcited α-enamine acids
  作者：Zhiqiang Pan、Fengchi Hu、Di Jiang、Yuchang Liu、Chengfeng Xia

  DOI：10.1039/d0cc07636h

  日期：——

  Chichibabin pyridinium synthesis between α-amino acids and aldehydes was developed. When the in situ generated α-enamine acids were photoexcited, they were oxidized by aerobic oxygen to give radical cation species. After decarboxylation and further oxidation, the generated iminium undergoes Chichibabin cyclization to afford pyridiniums. This photochemical protocol enables the synthesis of various tetra-substituted

  开发了可见光诱导的α-氨基酸和醛之间的脱羧壳多糖的吡啶鎓合成。当原位生成的α-烯胺酸被光激发时，它们被好氧氧化，产生自由基阳离子。脱羧并进一步氧化后，生成的亚胺盐经过Chichibabin环化得到吡啶鎓。这种光化学方法可以一步合成各种四取代吡啶鎓和相关的天然产物。