N-acryloyl-2-allylpiperidine | 768369-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-acryloyl-2-allylpiperidine
• 英文别名: 1-(2-Prop-2-enylpiperidin-1-yl)prop-2-en-1-one
• CAS: 768369-98-8
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: FCCUQYMGDLHKEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-acryloyl-2-allylpiperidine 在 palladium on activated charcoal 、 Grubbs catalyst first generation 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 65.0h， 生成 8-(4-dibenzylamino-butyl)-octadecahydro-4a,8-diaza-benzocycloheptadecen-9-one
  参考文献：
  名称：

  Efficient Syntheses of Oncinotine and Neooncinotine

  摘要：

  We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components: 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage: the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.

  DOI：

  10.1021/jo049526i
• 作为产物：
  描述：

  2-allylpiperidine trifluoroacetate 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到N-acryloyl-2-allylpiperidine
  参考文献：
  名称：

  Efficient Syntheses of Oncinotine and Neooncinotine

  摘要：

  We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components: 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage: the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.

  DOI：

  10.1021/jo049526i

文献信息

• Efficient Syntheses of Oncinotine and Neooncinotine
  作者：Duen-Ren Hou、Hsiu-Yi Cheng、Eng-Chi Wang

  DOI：10.1021/jo049526i

  日期：2004.9.1

  We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components: 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage: the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.