9-(3-dibenzylamino-propyl)-octadecahydro-4a,9-diaza-benzocyclooctadecen-10-one | 62074-29-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 9-(3-dibenzylamino-propyl)-octadecahydro-4a,9-diaza-benzocyclooctadecen-10-one
• 英文别名: N,N-Dibenzylneooncinotin；6-[3-(Dibenzylamino)propyl]-1,6-diazabicyclo[16.4.0]docosan-7-one
• CAS: 62074-29-7
• 化学式: C₃₇H₅₇N₃O
• 分子量: 559.879
• InChiKey: SQPNRBRRCVARTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(3-dibenzylamino-propyl)-octadecahydro-4a,9-diaza-benzocyclooctadecen-10-one 在 palladium dihydroxide ammonium formate 作用下， 以 乙醇 为溶剂， 反应 19.0h， 以70%的产率得到neooncinotine
  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：

  1-Amino-3-dibenzylaminopropane 在 palladium on activated charcoal 、 Grubbs catalyst first generation 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、2.03 MPa 条件下， 反应 57.0h， 生成 9-(3-dibenzylamino-propyl)-octadecahydro-4a,9-diaza-benzocyclooctadecen-10-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

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.