N-(3-dibenzylaminopropyl)-4-oxo-4-(2-allylpiperidinyl)butyramide | 768370-02-1

• 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-(3-dibenzylaminopropyl)-4-oxo-4-(2-allylpiperidinyl)butyramide
• 英文别名: N-[3-(dibenzylamino)propyl]-4-oxo-4-(2-prop-2-enylpiperidin-1-yl)butanamide
• CAS: 768370-02-1
• 化学式: C₂₉H₃₉N₃O₂
• 分子量: 461.648
• InChiKey: IOWLXACSPIFLLG-UHFFFAOYSA-N

物化性质

• 沸点：
  650.2±50.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-dibenzylaminopropyl)-4-oxo-4-(2-allylpiperidinyl)butyramide 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-[3-(dibenzylamino)propyl]-N-[4-(2-prop-2-enylpiperidin-1-yl)butyl]dec-9-enamide
  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-(3-(dibenzylamino)propyl)isoindoline-1,3-dione 在 一水合肼 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 27.5h， 生成 N-(3-dibenzylaminopropyl)-4-oxo-4-(2-allylpiperidinyl)butyramide
  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.