1-(naphthalen-1-yl)hex-2-yn-1-one | 1072835-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-1-yl)hex-2-yn-1-one
• CAS: 1072835-14-3
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: BKUCVPYIEXOSEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(naphthalen-1-yl)hex-2-yn-1-one 、 二苯亚甲基甘氨酸乙酯 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 1.17h， 以81%的产率得到3-(diphenylmethyleneamino)-6-(naphthalen-1-yl)-4-propyl-2H-pyran-2-one
  参考文献：
  名称：

  电子缺陷炔烃与N-（二苯基亚甲基）甘氨酸盐的迈克尔加成-内酯化反应：3-氨基-2-吡喃酮衍生物的高效合成

  摘要：

  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

  DOI：

  10.1055/s-0029-1217098

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。
• 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.