6-iodo-1-phenylhex-2-yn-1-one | 899434-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-iodo-1-phenylhex-2-yn-1-one
• CAS: 899434-11-8
• 化学式: C₁₂H₁₁IO
• 分子量: 298.123
• InChiKey: WVGMVWAILOOSKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-iodo-1-phenylhex-2-yn-1-one 、 3-氯丙胺盐酸盐 在 4 A molecular sieve 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以70%的产率得到(1,2,3,5,6,7-hexahydroindolizin-8-yl)(phenyl)methanone
  参考文献：
  名称：

  A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues

  摘要：

  The omega-iodo-alpha,beta-alkynoates and their ketone, sulfone or phosphonate analogues react with delta-chloropropylamines in MeCN assisted with K2CO3 to undergo a sequential S(N)2/Michael addition/S(N)2/S(N)2 reaction process, giving polysubstituted indolizidines or quinolizidines in good to excellent yields. This sequential reaction process is also compatible with three other substituted alpha,beta-alkynoates, affording quinolizidine analogues in moderate to good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.068
• 作为产物：
  描述：

  2-(戊-4-炔-1-氧基)四氢呋喃 在 正丁基锂 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 25.25h， 生成 6-iodo-1-phenylhex-2-yn-1-one
  参考文献：
  名称：

  A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues

  摘要：

  The omega-iodo-alpha,beta-alkynoates and their ketone, sulfone or phosphonate analogues react with delta-chloropropylamines in MeCN assisted with K2CO3 to undergo a sequential S(N)2/Michael addition/S(N)2/S(N)2 reaction process, giving polysubstituted indolizidines or quinolizidines in good to excellent yields. This sequential reaction process is also compatible with three other substituted alpha,beta-alkynoates, affording quinolizidine analogues in moderate to good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.068

文献信息

• Synthesis of Fused Tricyclic Amines Bearing Tetrasubstituted Carbons Using an Alkylation–Cyclization–Isomerization–3-aza-Cope Cascade Reaction
  作者：Takeo Sakai、Tomoki Furuhata、Kota Hosoe、Kaho Umemura、Yuji Mori

  DOI：10.1021/acs.orglett.3c00778

  日期：2023.5.5

  A new cascade reaction sequence that involves alkylation, cyclization, isomerization, and 3-aza-Cope rearrangement was discovered. The stereogenic centers of the starting piperidines were transferred to the bicyclic enamine products, and a range of electron-withdrawing groups on the alkyne moieties, from ketones to amides, were tolerated under the reaction conditions. The bicyclic enamines underwent

  发现了涉及烷基化、环化、异构化和 3-aza-Cope 重排的新级联反应序列。起始哌啶的立体异构中心被转移到双环烯胺产物上，并且在反应条件下可以容忍炔烃部分上的一系列吸电​​子基团，从酮到酰胺。双环烯胺经过三氟乙酸 (TFA) 介导的环化形成带有四取代碳的三环胺。