6-(but-2-ynyl)quinoline | 1234580-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(but-2-ynyl)quinoline
• 英文别名: 6-But-2-ynylquinoline；6-but-2-ynylquinoline
• CAS: 1234580-67-6
• 化学式: C₁₃H₁₁N
• 分子量: 181.237
• InChiKey: WFYRWWRTCCQTTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  quinolin-6-ylmethyl but-2-ynoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以88%的产率得到6-(but-2-ynyl)quinoline
  参考文献：
  名称：

  Decarboxylative Benzylations of Alkynes and Ketones

  摘要：

  Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.

  DOI：

  10.1021/ja1035557

文献信息

• Alkyne Compounds for Treatment of Complement Mediated Disorders
  申请人：ACHILLION PHARMACEUTICALS, INC.

  公开号：US20150239868A1

  公开（公告）日：2015-08-27

  Compounds, methods of use, and processes for making inhibitors of complement factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof, wherein R 12 or R 13 on the A group is an alkyne (R 32 ) are provided. The inhibitors described herein target factor D and inhibit or regulate the complement cascade at an early and essential point in the alternative complement pathway, and reduce factor D's ability to modulate the classical and lectin complement pathways. The inhibitors of factor D described herein are capable of reducing the excessive activation of complement, which has been linked to certain autoimmune, inflammatory, and neurodegenerative diseases, as well as ischemia-reperfusion injury and cancer.

  本文提供了包含化合物I式，或其药学上可接受的盐或组成物的补体因子D抑制剂的制备方法和使用方法，其中A组上的R12或R13是炔基（R32）。所述的抑制剂靶向因子D，并在替代补体途径的早期和关键点抑制或调节补体级联反应，并减少因子D调节经典和凝集素补体途径的能力。本文所述的因子D抑制剂能够减少过度激活补体，这与某些自身免疫性、炎症性和神经退行性疾病以及缺血再灌注损伤和癌症有关。
• US9828396B2
  申请人：——

  公开号：US9828396B2

  公开（公告）日：2017-11-28
• Decarboxylative Benzylations of Alkynes and Ketones
  作者：Robert R. P. Torregrosa、Yamuna Ariyarathna、Kalicharan Chattopadhyay、Jon A. Tunge

  DOI：10.1021/ja1035557

  日期：2010.7.14

  Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.