(+/-)-cleavamine | 31679-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-cleavamine
• 英文别名: cleavamine；9-ethyl-5,8,11,12,13,14-hexahydro-6H-7,14-diaza-7,11-methano-cycloundeca[a]indene；Cleavamin；17-Ethyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,16-pentaene
• CAS: 31679-35-3
• 化学式: C₁₉H₂₄N₂
• 分子量: 280.413
• InChiKey: GWRGHAJVUZLGHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  ethyl 1,6-dihydro-3(2H)-pyridinone-1-carboxylate 在 盐酸 、 氢氧化钾 、 lithium aluminium tetrahydride 、 mercury(II) diacetate 、 对甲苯磺酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 苯 为溶剂， 反应 129.19h， 生成 (+/-)-cleavamine
  参考文献：
  名称：

  1,6-Dihydro-3(2H)-pyridinones. IV. Synthesis of (.+-.)-tabersonine and (.+-.)-cleavamine via a common intermediate, ethyl 3-ethyl-3-hydroxy-1,2,3,6-tetrahydropyridine-1-carboxylate.

  摘要：

  通过由 1, 6-二氢-3 (2H)- 吡啶酮-1-羧酸乙酯 (5a) 衍生出的共同中间体 (6) 实现了 (±)-tabersonine (1) 的正式合成和 (±)-cleavamine (2) 的全合成。此外，还讨论了羧酸 (20) 成功环化为二氧环拉明 (4) 的过程。

  DOI：

  10.1248/cpb.31.1183

文献信息

• 1,6-Dihydro-3(2H)-pyridinones as synthetic intermediates. A convenient total synthesis of (.+-.)-cleavamine.
  作者：TAKESHI IMANISHI、AKIRA NAKAI、NORIYUKI YAGI、MIYOJI HANAOKA

  DOI：10.1248/cpb.29.901

  日期：——

  A novel and convenient total synthesis of (±)-cleavamine (1) starting from ethyl 1, 6-dihydro-3 (2H)-pyridinone-1-carboxylate (2) is described.

  本文描述了一种新颖且便捷的从1,6-二氢-3(2H)-吡啶酮-1-羧酸乙酯(2)出发合成(±)-克利瓦明(1)的方法。
• A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis−Vinyl Halide Heck Cyclization Strategy
  作者：M.-Lluïsa Bennasar、Daniel Solé、Ester Zulaica、Sandra Alonso

  DOI：10.1021/ol200437k

  日期：2011.4.15

  An indole-templated ring-closing metathesis has been used to create the central nine-membered ring of the cleavamine-type alkaloids. A subsequent intramolecular vinyl halide Heck reaction upon the resulting azacyclononene ring completes the assembly of the strained 1-azabicyclo[6.3.1]dodecane framework of the alkaloids. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine.
• Synthesis of cleavamine-type indole alkaloids and their 5-nor derivatives by a ring-closing metathesis–vinyl halide Heck cyclization strategy
  作者：M.-Lluïsa Bennasar、Daniel Solé、Ester Zulaica、Sandra Alonso

  DOI：10.1016/j.tet.2013.01.064

  日期：2013.3

  An indole-templated RCM has been used to assemble the central medium-sized rings of the indole upper-half of vinorelbine and the cleavamine-type alkaloids. From these key intermediates, the bridged tetracyclic framework of the alkaloids is completed with the insertion of a 2-ethylpropeno unit, by N-alkylation followed by a challenging endocyclic vinyl halide Heck cyclization. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine. (C) 2013 Elsevier Ltd. All rights reserved.
• 1,6-Dihydro-3(2H)-pyridinones. IV. Synthesis of (.+-.)-tabersonine and (.+-.)-cleavamine via a common intermediate, ethyl 3-ethyl-3-hydroxy-1,2,3,6-tetrahydropyridine-1-carboxylate.
  作者：TAKESHI IMANISHI、HIROAKI SHIN、NORIYUKI YAGI、AKIRA NAKAI、MIYOJI HANAOKA

  DOI：10.1248/cpb.31.1183

  日期：——

  A formal synthesis of (±)-tabersonine (1) and a total synthesis of (±)-cleavamine (2) have been achieved via a common intermediate (6) derived from ethyl 1, 6-dihydro-3 (2H)-pyridinone-1-carboxylate (5a). The successful cyclization of the carboxylic acid (20) to the dioxocleavamine (4) is also discussed.

  通过由 1, 6-二氢-3 (2H)- 吡啶酮-1-羧酸乙酯 (5a) 衍生出的共同中间体 (6) 实现了 (±)-tabersonine (1) 的正式合成和 (±)-cleavamine (2) 的全合成。此外，还讨论了羧酸 (20) 成功环化为二氧环拉明 (4) 的过程。