1-(4-nitrophenyl)hex-2-yn-1-one | 1071005-56-5

• 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: 1-(4-nitrophenyl)hex-2-yn-1-one
• CAS: 1071005-56-5
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: POKTXNBIKGGPGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)hex-2-yn-1-one 、 N-亚苄基-4-甲基苯磺酰胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以42%的产率得到(E)-2-(3-ethyl-4-phenyl-1-tosylazetidin-2-ylidene)-1-(4-nitrophenyl)ethanone
  参考文献：
  名称：

  Cycloaddition of Alkynyl Ketones with N-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines

  摘要：

  Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.

  DOI：

  10.1021/jo801687v
• 作为产物：
  描述：

  1-戊炔 、 4-硝基苯甲酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以93%的产率得到1-(4-nitrophenyl)hex-2-yn-1-one
  参考文献：
  名称：

  聚苯乙烯负载的溴化锌-乙二胺配合物是可重复使用且高效的多相催化剂，用于合成α，β-乙炔酮

  摘要：

  聚苯乙烯负载的溴化锌-乙二胺络合物已显示出可作为可循环利用的非均相催化剂，用于通过酰基氯与末端炔烃的交叉偶联快速有效地合成α，β-炔酮。该催化剂在反应条件下易于制备，稳定，可重复使用和有效。 多相催化-交叉偶联-酰氯-炔烃-酮

  DOI：

  10.1055/s-0030-1258365

文献信息

• PPh₃-KOBu^t–Mediated Cyclization Reaction of <font>β</font>-Ketoesters with Alkynyl Ketones: Synthesis of Functionalized 2-Pyrones
  作者：Bin Hu、Ling-Guo Meng、Xiao-Li Hao、Mao Liang、Song Xue

  DOI：10.1080/00397911.2010.517374

  日期：2011.11.1

  Abstract Cyclization of alkynyl ketones with β-ketoesters mediated by PPh3 and KOBut to synthesize 2-pyrone derivatives was systematically described. A variety of β-ketoesters reacted with alkynyl ketones to give functionalized 2-pyrones in moderate to good yields under mild conditions.

  摘要 系统地描述了由 PPh3 和 KOBut 介导的炔基酮与 β-酮酯环化合成 2-吡喃酮衍生物。各种 β-酮酯与炔基酮反应，在温和条件下以中等至良好的产率得到官能化的 2-吡喃酮。
• Michael Addition-Lactonization Reaction of Electron-Deficient Alkynes with N-(Diphenylmethylene)glycinates: An Efficient Synthesis of 3-Amino-2-pyrone Derivatives
  作者：Tao Lu、Qing-Fa Zhou、Yong Zhu、Wei-Fang Tang

  DOI：10.1055/s-0029-1217098

  日期：2010.1

  approach is based on the Michael addition of N-(diphenylmethylene)glycinates to various alkynyl ketones, followed by lactonization using 10 mol% sodium hydroxide as catalyst. Aromatic and aliphatic alkynyl ketones were converted into the corresponding 3-amino-2-pyrone derivatives in moderate to high yields. When methyl propiolate was submitted to the reaction, α,β-dehydroamino acids were formed in good

  已经开发了温和而有效的合成3-氨基-2-吡喃酮衍生物的方法。该方法基于将N-（二苯基亚甲基）甘氨酸盐迈克尔加成到各种炔基酮中，然后使用10mol％氢氧化钠作为催化剂进行内酯化。将芳族和脂族炔基酮以中等至高产率转化为相应的3-氨基-2-吡喃酮衍生物。当丙酸甲酯进行反应时，以良好的产率形成α，β-脱氢氨基酸。 3-氨基-2-吡喃酮衍生物-炔基酮-迈克尔加成-内酯化-合成
• Polystyrene-Supported Zinc Bromide-Ethylenediamine Complex as a Reusable and Highly Efficient Heterogeneous Catalyst for the Synthesis of α,β-Acetylenic Ketones
  作者：Ali Keivanloo、Mohammad Bakherad、Bahram Bahramian、Mahrokh Rahmani、Sayed Taheri

  DOI：10.1055/s-0030-1258365

  日期：2011.1

  A polystyrene-supported zinc bromide-ethylenediamine complex was shown to be useful as a recyclable heterogeneous catalyst for the rapid and efficient synthesis of α,β-acetylenic ketones in good-to-excellent yields by cross-coupling of acid chlorides with terminal alkynes. The catalyst is easily prepared, stable, reusable, and efficient under the reaction conditions. heterogeneous catalysis - cross-coupling

  聚苯乙烯负载的溴化锌-乙二胺络合物已显示出可作为可循环利用的非均相催化剂，用于通过酰基氯与末端炔烃的交叉偶联快速有效地合成α，β-炔酮。该催化剂在反应条件下易于制备，稳定，可重复使用和有效。 多相催化-交叉偶联-酰氯-炔烃-酮
• Cycloaddition of Alkynyl Ketones with <i>N</i>-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines
  作者：Ling-Guo Meng、Peijie Cai、Qingxiang Guo、Song Xue

  DOI：10.1021/jo801687v

  日期：2008.11.7

  Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.