methyl 6-bromoindolizine-2-carboxylate | 1162262-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: methyl 6-bromoindolizine-2-carboxylate
• CAS: 1162262-40-9
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: LYYYHGGXOLUMEM-UHFFFAOYSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 6-bromoindolizine-2-carboxylate 在 palladium diacetate 作用下， 以 Petroleum ether 为溶剂， 生成 (6-cyclopropylindolizin-2-yl)methanol
  参考文献：
  名称：

  INHIBITORS OF PLASMA KALLIKREIN AND USES THEREOF

  摘要：

  本发明提供了作为血浆激肽酶抑制剂并具有相同理想特性的化合物和组合物。

  公开号：

  US20190284182A1
• 作为产物：
  描述：

  5-溴-2-吡啶甲醛 在 三乙烯二胺 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 乙酸酐 为溶剂， 反应 6.0h， 生成 methyl 6-bromoindolizine-2-carboxylate
  参考文献：
  名称：

  吲哚嗪衍生物作为α-7nAChR激动剂的合成及生物活性

  摘要：

  人α7烟碱乙酰胆碱受体（nAChR）是治疗伴有认知障碍的精神分裂症的有前途的治疗靶标。在本文中，我们报告了一系列针对α7nAChR的吲哚嗪衍生物的合成和激动活性。结果表明，所有合成的化合物均对α7nAChR具有亲和力，并且某些化合物具有很强的激动活性，特别是大多数活性激动剂均显示出比对照EVP-6124更高的效力。对接和结构-活性关系研究为开发更有效的新型α7nAChR激动剂提供了见识。

  DOI：

  10.1016/j.ejmech.2016.03.016

文献信息

• Catalytic Asymmetric Conjugate Addition of Indolizines to α,β-Unsaturated Ketones
  作者：José Tiago Menezes Correia、Benjamin List、Fernando Coelho

  DOI：10.1002/anie.201700513

  日期：2017.6.26

  A catalytic enantioselective conjugate addition of indolizines to enones is described. The chiral phosphoric acid (S)‐TRIP activates α,β‐unsaturated ketones, thereby promoting an enantioface‐differentiating attack by indolizines. Using this reaction, several alkylated indolizines were synthesized in good yields and with enantiomeric ratios of up to 98:2.

  描述了吲哚向烯酮的催化对映体选择性共轭加成。手性磷酸（S）-TRIP激活α，β-不饱和酮，从而促进吲哚嗪类药物的对映体分化攻击。使用该反应，以高收率和高达98：2的对映体比例合成了几种烷基化的吲哚嗪。
• Brønsted-acid-catalyzed selective Friedel–Crafts monoalkylation of isatins with indolizines in water
  作者：Bruno Boni Guidotti、Thiago Sabino da Silva、José Tiago Menezes Correia、Fernando Coelho

  DOI：10.1039/d0ob01714k

  日期：——

  The controlled mono-addition of indolizines to isatins under very mild conditions is described. The reaction occurs in water using diphenylphosphate as the catalyst, which is dramatically accelerated by surfactant addition. 3-Hydroxy-3-indolizinyl-2-oxindole scaffolds were synthesized in up to >99% yield. Notably, in organic solvents only bis-addition products were observed.

  描述了在非常温和的条件下将中氮茚单添加到靛红中。该反应在水中发生，使用磷酸二苯酯作为催化剂，加入表面活性剂可显着加速该反应。3-Hydroxy-3-indolizinyl-2-oxindole 支架的合成产率高达 >99%。值得注意的是，在有机溶剂中仅观察到双加成产物。
• Inhibitors of plasma kallikrein and uses thereof
  申请人：Shire Human Genetic Therapies, Inc.

  公开号：US10730874B2

  公开（公告）日：2020-08-04

  The present invention provides compounds and compositions thereof which are useful as inhibitors of plasma kallikrein and which exhibit desirable characteristics for the same.

  本发明提供了可用作血浆钙激酶抑制剂并表现出理想特性的化合物及其组合物。
• Catalyst-Free Conjugate Addition of Indolizines to <i>In Situ</i>-Generated Oxidized Morita–Baylis–Hillman Adducts
  作者：Thiago S. Silva、Lucas A. Zeoly、Fernando Coelho

  DOI：10.1021/acs.joc.0c00189

  日期：2020.4.17

  Sequential one-pot 2-iodoxybenzoic acid (IBX) oxidation of Morita-Baylis-Hillman (MBH) adducts followed by catalyst-free indolizine conjugate addition was developed. The wide scopes of MBH adducts and indolizines were investigated, and densely functionalized adducts were obtained in yields of up to 94%. The conjugate addition step occurred in less than a minute at room temperature with total regioselectivity toward indolizine C3 carbon. Less nucleophilic C1 carbon was also alkylated when C3-substituted indolizines were employed as the substrate.
• SUBSTITUTED IMIDAZOPYRIDINES AS INHIBITORS OF PLASMA KALLIKREIN AND USES THEREOF
  申请人：Shire Human Genetic Therapies, Inc.

  公开号：EP3765459A1

  公开（公告）日：2021-01-20