(E)-N-allyl-5-(β-styryl)-4-pentynamide | 1374311-42-8

• 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: (E)-N-allyl-5-(β-styryl)-4-pentynamide
• 英文别名: (E)-7-phenyl-N-prop-2-enylhept-6-en-4-ynamide
• CAS: 1374311-42-8
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: XAHZOBBPDYARJG-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-allyl-5-(β-styryl)-4-pentynamide 在 L-Selectride 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 2,2,2-三氟乙醇 为溶剂， 反应 2.5h， 生成 (+/-)-(5R,1'R)-N-allyl-5-(1-hydroxy-3-phenylallyl)-pyrrolidin-2-one
  参考文献：
  名称：

  Application of the intramolecular PIFA-mediated amidation of alkynes to the synthesis of substituted indolizidinones

  摘要：

  The construction of the title compounds has been achieved from properly substituted linear alkynylamides through the suitable combination of two key cyclization steps. First, an intramolecular PIFA-mediated alkyne amidation protocol leads to the creation of the pyrrolidinone nucleus, which under proper manipulation of the generated keto carbonyl group permits the assembling of the indolizidinone skeleton by the introduction of a subsequent ring closing olefin metathesis step. Finally, its transformation into a series of substituted mono- and trihydroxylated indolizidinone derivatives is achieved by manipulation of the remaining unsaturated fragment under hydrogenation and dihydroxylation conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.033
• 作为产物：
  描述：

  炔丙基脲 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-N-allyl-5-(β-styryl)-4-pentynamide
  参考文献：
  名称：

  Application of the intramolecular PIFA-mediated amidation of alkynes to the synthesis of substituted indolizidinones

  摘要：

  The construction of the title compounds has been achieved from properly substituted linear alkynylamides through the suitable combination of two key cyclization steps. First, an intramolecular PIFA-mediated alkyne amidation protocol leads to the creation of the pyrrolidinone nucleus, which under proper manipulation of the generated keto carbonyl group permits the assembling of the indolizidinone skeleton by the introduction of a subsequent ring closing olefin metathesis step. Finally, its transformation into a series of substituted mono- and trihydroxylated indolizidinone derivatives is achieved by manipulation of the remaining unsaturated fragment under hydrogenation and dihydroxylation conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.033

文献信息

• Application of the intramolecular PIFA-mediated amidation of alkynes to the synthesis of substituted indolizidinones
  作者：Leticia M. Pardo、Imanol Tellitu、Esther Domínguez

  DOI：10.1016/j.tet.2012.03.033

  日期：2012.5

  The construction of the title compounds has been achieved from properly substituted linear alkynylamides through the suitable combination of two key cyclization steps. First, an intramolecular PIFA-mediated alkyne amidation protocol leads to the creation of the pyrrolidinone nucleus, which under proper manipulation of the generated keto carbonyl group permits the assembling of the indolizidinone skeleton by the introduction of a subsequent ring closing olefin metathesis step. Finally, its transformation into a series of substituted mono- and trihydroxylated indolizidinone derivatives is achieved by manipulation of the remaining unsaturated fragment under hydrogenation and dihydroxylation conditions. (C) 2012 Elsevier Ltd. All rights reserved.