6-chloro-2-vinylchroman-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-chloro-2-vinylchroman-4-one
• 英文别名: 6-Chloro-2-ethenyl-2,3-dihydrochromen-4-one
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: NZSPSDDRGMTEHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (6-Chlorochromenylium-4-yl)oxy-trimethylsilane;trifluoromethanesulfonate 、 乙烯基氯化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 6-chloro-2-vinylchroman-4-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 2-alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones and 2-alkenylquinol-4-ones

  摘要：

  2-Alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones, and 2-alkenylquinol-4-ones were prepared with very good regioselectivity by Me3SiOTf-mediated conjugate addition of alkenylmagnesium bromides and alkenyllithium compounds to chromones thiochromones, and quinol-4-ones. A number of products exhibit a considerable antimicrobial activity. The best activity, with respect to the spectrum of antimicrobial activity, was observed for 2-vinylchroman-4-ones containing an unsubstituted vinyl group and a chloride group located at the chromanone moiety. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.043

文献信息

• [DE] NEUE ANTIMIKROBIELLE CHROMAN-4-ONE<br/>[EN] NOVEL ANTIMICROBIAL CHROMAN-4-ONES<br/>[FR] NOUVELLES CHROMAN-4-ONES ANTIMICROBIENNES
  申请人：UNIV ERNST MORITZ ARNDT

  公开号：WO2004113317A1

  公开（公告）日：2004-12-29

  Die Erfindung betrifft unter anderem neue Chroman-4-one der allgemeinen Formel (I) Verfahren zur Herstellung derselben sowie deren Verwendung als antimikrobielle Wirkstoffe.

  该发明涉及新的通式(I)的Chroman-4-one，其制备方法以及其作为抗微生物药物的用途。
• Synthesis and structure–activity relationships of 2-vinylchroman-4-ones as potent antibiotic agents
  作者：Uwe Albrecht、Michael Lalk、Peter Langer

  DOI：10.1016/j.bmc.2004.12.031

  日期：2005.3.1

  A series of novel 2-vinylchroman-4-ones, analogues of the natural products Aposphaerin A and B, were identified as potent antibiotics. Derivatives exhibit a significant activity against multiresistant strains of S. aureus, such as MRSA (methicillin resistant S. aureus). The 2-vinylchroman-4-ones were efficiently prepared by Lewis acid mediated conjugate addition of vinylmagnesium bromide to chromones. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial activity of 2-alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones and 2-alkenylquinol-4-ones
  作者：Nicole Hoettecke、Sven Rotzoll、Uwe Albrecht、Michael Lalk、Christine Fischer、Peter Langer

  DOI：10.1016/j.bmc.2008.10.043

  日期：2008.12.15

  2-Alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones, and 2-alkenylquinol-4-ones were prepared with very good regioselectivity by Me3SiOTf-mediated conjugate addition of alkenylmagnesium bromides and alkenyllithium compounds to chromones thiochromones, and quinol-4-ones. A number of products exhibit a considerable antimicrobial activity. The best activity, with respect to the spectrum of antimicrobial activity, was observed for 2-vinylchroman-4-ones containing an unsubstituted vinyl group and a chloride group located at the chromanone moiety. (C) 2008 Elsevier Ltd. All rights reserved.