rac-(2R*,6aS*,10aS*)-3-(t-butoxycarbonyl)-2-formyl-5,10-dioxo-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline 5-ethylene ketal

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: rac-(2R*,6aS*,10aS*)-3-(t-butoxycarbonyl)-2-formyl-5,10-dioxo-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline 5-ethylene ketal
• 英文别名: tert-butyl (4'aS,7'aS,9'R,10'aS)-9'-formyl-1'-oxospiro[1,3-dioxolane-2,6'-3,4,4a,5,7,7a,9,10-octahydro-2H-pyrrolo[2,3-i]isoquinoline]-8'-carboxylate
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: OJIQZSFWDCKGQM-LJPSSGMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  rac-(2R*,6aS*,10aS*)-3-(t-butoxycarbonyl)-2-formyl-5,10-dioxo-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline 5-ethylene ketal 在 双(三甲基硅烷基)氨基钾 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  An efficient access to the optically active manzamine tetracyclic ring system

  摘要：

  The highly stereoselective synthesis of the optically active tetracyclic core 2 of Manzamine A 1 was achieved via the Diels-Alder reaction of dihydropyridinone 12b, derived from L-serine, with siloxydienes, followed by sequential new and conventional pathways. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80033-6
• 作为产物：
  描述：

  N-benzenesulfonyl-3-<2-methoxycarbonyl-2-amino>ethyl>-5,6-dihydro-2(1H)-pyridinone 在 三乙烯二胺 、 aluminum oxide 、 sodium hydroxide 、 锂硼氢 、 硼酸三甲酯 、 蒽 、 camphor-10-sulfonic acid 、 sodium 、 4-甲基苯磺酸吡啶 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 rac-(2R*,6aS*,10aS*)-3-(t-butoxycarbonyl)-2-formyl-5,10-dioxo-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline 5-ethylene ketal
  参考文献：
  名称：

  Dihydropyridinone approach to manzamines: An expedient construction of the tetracyclic core of manzamine A

  摘要：

  A construction of the central tetracyclic core (19) of manzamine A (1) was successfully achieved by a highly efficient Diels-Alder reaction of the suitably protected dihydropyridinones (5) and Danishefsky's diene as a key strategy. Expedient conversion of the D-A product (7) to the precursor (15) was followed by the azocine lactam ring closure to furnish the titled core.

  DOI：

  10.1016/0040-4039(93)88081-s

文献信息

• Synthesis of a tetracyclic substructure of manzamine A via the Diels-Alder reaction of dihydropyridinones
  作者：Yasuhiro Torisawa、Toshihiro Hosaka、Kiyoshi Tanabe、Naoko Suzuki、Yumiko Motohashi、Tohru Hino、Masako Nakagawa

  DOI：10.1016/0040-4020(96)00607-2

  日期：1996.8

  A (1) was achieved via Diels-Alder reaction of the dihydropyridinones (5, 6). Conversion of the two D-A products (7, 8) to the key tricyclic ketone (10) was conducted through a conventional pathway (Scheme III) as well as a new pathway developed (Scheme IV). For effective construction of the required azocine ring systems, model studies were carried out to find intramolecular amide formation by pentafluorophenyl

  四环核心的合成（19 manzamine A（的）1）经由该dihydropyridinones（的狄尔斯-阿尔德反应来实现5，6）。两个DA产物（转化7，8）的键三环酮（10）通过常规途径（方案III）以及显影（方案IV）的新途径被进行。为了有效构建所需的偶氮电影环系统，进行了模型研究，以发现五氟苯基酯和DPPA方法形成的分子内酰胺，将其成功应用于实际底物上以提供标题的核结构（19）。
• An efficient access to the optically active manzamine tetracyclic ring system
  作者：Hideharu Uchida、Atsushi Nishida、Masako Nakagawa

  DOI：10.1016/s0040-4039(98)80033-6

  日期：1999.1

  The highly stereoselective synthesis of the optically active tetracyclic core 2 of Manzamine A 1 was achieved via the Diels-Alder reaction of dihydropyridinone 12b, derived from L-serine, with siloxydienes, followed by sequential new and conventional pathways. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Dihydropyridinone approach to manzamines: An expedient construction of the tetracyclic core of manzamine A
  作者：Masako Nakagawa、Yasuhiro Torisawa、Toshihiro Hosaka、Kiyoshi Tanabe、Tadamasa Da-te、Kimio Okamura、Tohru Hino

  DOI：10.1016/0040-4039(93)88081-s

  日期：1993.7

  A construction of the central tetracyclic core (19) of manzamine A (1) was successfully achieved by a highly efficient Diels-Alder reaction of the suitably protected dihydropyridinones (5) and Danishefsky's diene as a key strategy. Expedient conversion of the D-A product (7) to the precursor (15) was followed by the azocine lactam ring closure to furnish the titled core.