| 1253801-94-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• CAS: 1253801-94-3
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: QMWNTLMVBUJGND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  、 丙炔酸甲酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以63%的产率得到
  参考文献：
  名称：

  Facile synthesis of highly functionalized six-membered heterocycles via PPh3-catalyzed [4+2] annulations of activated terminal alkynes and hetero-dienes: scope, mechanism, and application

  摘要：

  A novel [4+2] annulation between activated terminal alkynes and aza-dienes or oxo-dienes has been developed with the use of triphenylphosphine catalyst (20 mol %), which provides a facile method for synthesis of the corresponding highly functionalized dihydropyridines or dihydropyrans in good to excellent yields. The reaction mechanism has also been established, consisting formal hetero-Diels-Alder reaction catalyzed by PPh3 and [1,3]-proton transfer, which exhibits a large isotopic effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.043

文献信息

• Enantioselective Amine-Catalyzed [4+2] Annulations of Allenoates and Oxo-dienes: An Asymmetric Synthesis of Dihydropyrans
  作者：Xiaojun Wang、Tong Fang、Xiaofeng Tong

  DOI：10.1002/anie.201100945

  日期：2011.5.27

  dihydropyrans have been prepared in high to excellent yields and enantioselectivities (see scheme). The interaction between functional groups in the zwitterionic intermediate, which is generated by addition of the amine catalyst to the allenoate substrate, is thought to play a crucial role in the stereochemical outcome. Bn=benzyl, DMAP=4‐dimethylaminopyridine.

  已经以高至优异的产率和对映选择性制备了生物学上显着的多取代的二氢吡喃（参见方案）。两性离子中间体中官能团之间的相互作用（这是通过将胺催化剂添加到烯丙酸酯底物上而产生的）被认为在立体化学结果中起着至关重要的作用。Bn =苄基，DMAP = 4-二甲基氨基吡啶。