7-iodo-1-phenylhept-2-yn-1-one | 184641-58-5

• 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: 7-iodo-1-phenylhept-2-yn-1-one
• CAS: 184641-58-5
• 化学式: C₁₃H₁₃IO
• 分子量: 312.15
• InChiKey: GZAMYQXYXDAKCL-UHFFFAOYSA-N

物化性质

• 沸点：
  363.5±44.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  7-iodo-1-phenylhept-2-yn-1-one 、 2-苯基氮丙啶 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以55%的产率得到phenyl(2-phenyl-2,3,5,6,7,8-hexahydroindolizin-1-yl)methanone
  参考文献：
  名称：

  A Formal [3+2] Cycloaddition Process with Nonactivated Aziridines to Polysubstituted Indolizidines

  摘要：

  [chemical reaction: see text]. Heating a mixture of ethyl 7-iodo-2-heptynoate (or its analogues), 2-aryl aziridines, and K2CO3 in dry CH(3)CN delivers polysubstituted indolizidines. This reaction goes through an S(N)2/formal [3+2] cycloaddition process and represents the first synthetically useful example of the formal [3+2] cycloaddition process through a C-N bond cleavage of nonactivated aziridines.

  DOI：

  10.1021/ol0513692
• 作为产物：
  描述：

  1-phenyl-7-(tetrahydro-furan-2-yloxy)-hept-2-yn-1-ol 在 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 7-iodo-1-phenylhept-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

• An Efficient Sequential Reaction Process to Polysubstituted Indolizidines and Quinolizidines and Its Application to the Total Synthesis of Indolizidine 223A
  作者：Wei Zhu、Dapeng Dong、Xiaotao Pu、Dawei Ma

  DOI：10.1021/ol047476y

  日期：2005.2.1

  The reaction of iodides 1 with delta-chloropropylamines 5 in MeCN assisted with K2CO3 undergoes a sequential S(N)2/Michael addition/SN2/SN2 reaction process to give polysubstituted indolizidines and quinolizidines. Using this method, indolizidine 223A is synthesized from 2-ethyl-2-hexenoic acid in 12 linear steps and 14.5% overall yield. [Reaction: see text]

  碘化物1与δ-氯丙胺5在MeCN中辅以K2CO3的反应按顺序进行S（N）2 / Michael加成/ SN2 / SN2反应，得到多取代的吲哚并咪唑和喹喔啉。使用该方法，由吲哚并咪唑223A由2-乙基-2-己酸以12个线性步骤合成，并且总产率为14.5％。[反应：请参阅文字]
• A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues
  作者：Guorong Cai、Wei Zhu、Dawei Ma

  DOI：10.1016/j.tet.2006.03.068

  日期：2006.6

  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.
• A Formal [3+2] Cycloaddition Process with Nonactivated Aziridines to Polysubstituted Indolizidines
  作者：Wei Zhu、Guorong Cai、Dawei Ma

  DOI：10.1021/ol0513692

  日期：2005.12.1

  [chemical reaction: see text]. Heating a mixture of ethyl 7-iodo-2-heptynoate (or its analogues), 2-aryl aziridines, and K2CO3 in dry CH(3)CN delivers polysubstituted indolizidines. This reaction goes through an S(N)2/formal [3+2] cycloaddition process and represents the first synthetically useful example of the formal [3+2] cycloaddition process through a C-N bond cleavage of nonactivated aziridines.