N-allyl-4-pentynamide | 1374311-41-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-allyl-4-pentynamide
• 英文别名: N-allylpent-4-ynamide；N-prop-2-enylpent-4-ynamide
• CAS: 1374311-41-7
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: GQUMLFGDAUMKTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  N-allyl-4-pentynamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 2,2,2-三氟乙醇 为溶剂， 反应 79.5h， 生成 (+/-)-(5R,1'S)-N-allyl-5-[1-hydroxy-1-(4-methoxyphenyl)allyl]-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 、 丙烯胺 在 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， 以82%的产率得到N-allyl-4-pentynamide
  参考文献：
  名称：

  Development of a New Nonsugar-Based Strategy for the Synthesis of the Hydroxylated Indolizidinone Skeleton

  摘要：

  由直链炔酰胺非对映控制形成多羟基化吲哚里西啶酮骨架是通过两个关键环化步骤的顺序组合来实现的。特别是，PIFA介导的分子内炔酰胺化反应提供了5-烯酰吡咯烷酮骨架，而随后的Ru催化的闭环复分解方案则组装了双环吲哚里西啶框架。在受控还原条件下对前一环化步骤中产生的酮羰基进行操作，并在 Upjohn 条件下对后一环化步骤中产生的 C6-C7 双键进行氧化，将 6,7,8-三羟基固定在完整的结构中。非对映选择性方式。

  DOI：

  10.1055/s-0031-1290604

文献信息

• Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1<i>H</i>)-ones via microwave-activated inverse electron-demand Diels–Alder reactions
  作者：Salah Fadel、Youssef Hajbi、Mostafa Khouili、Said Lazar、Franck Suzenet、Gérald Guillaumet

  DOI：10.3762/bjoc.10.24

  日期：——

  8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels-Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels-Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones

  取代的 3,4-dihydro-1,8-naphthyridin-2(1H)-ones 已通过逆电子需求 Diels-Alder 反应从带有酰基氨基和末端炔侧链的 1,2,4-三嗪合成. 炔烃首先与芳基卤化物进行 Sonogashira 交叉偶联反应，其产物然后进行分子内逆电子需求 Diels-Alder 反应，得到 5-aryl-3,4-dihydro-1,8-naphthyridin-2 (1H)-ones 通过有效的合成路线。
• 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.
• Development of a New Nonsugar-Based Strategy for the Synthesis of the Hydroxylated Indolizidinone Skeleton
  作者：Imanol Tellitu、Esther Domínguez、Leticia Pardo

  DOI：10.1055/s-0031-1290604

  日期：2012.4

  The diastereocontrolled formation of the polyhydroxylated indolizidinone skeleton from linear alkynylamides is achieved by the sequential combination of two key cyclization steps. In particular, a PIFA-mediated intramolecular alkyne amidation reaction affords the 5-alkenoylpyrrolidinone skeleton, whereas a subsequent Ru-catalyzed ring-closing-metathesis protocol assembles the bicyclic indolizidine framework. Manipulation of the ketone carbonyl group, developed in the former cyclization step under controlled reductive conditions, and oxidation of the C6-C7 double bond, generated in the latter one under Upjohn conditions, fix the 6,7,8-trihydroxy groups in a complete diastereoselective manner.

  由直链炔酰胺非对映控制形成多羟基化吲哚里西啶酮骨架是通过两个关键环化步骤的顺序组合来实现的。特别是，PIFA介导的分子内炔酰胺化反应提供了5-烯酰吡咯烷酮骨架，而随后的Ru催化的闭环复分解方案则组装了双环吲哚里西啶框架。在受控还原条件下对前一环化步骤中产生的酮羰基进行操作，并在 Upjohn 条件下对后一环化步骤中产生的 C6-C7 双键进行氧化，将 6,7,8-三羟基固定在完整的结构中。非对映选择性方式。