methyl 2-[3-vinyl-6-methyl-5-(methoxymethoxy)-1-(methoxycarbonyl)-2-piperidyl]acetate | 224183-92-0

• 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: methyl 2-[3-vinyl-6-methyl-5-(methoxymethoxy)-1-(methoxycarbonyl)-2-piperidyl]acetate
• 英文别名: methyl (2R,3R,5S,6S)-3-ethenyl-5-(methoxymethoxy)-2-(2-methoxy-2-oxoethyl)-6-methylpiperidine-1-carboxylate
• CAS: 224183-92-0
• 化学式: C₁₅H₂₅NO₆
• 分子量: 315.367
• InChiKey: KRSCCLJXNLSLAA-RVMXOQNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[3-vinyl-6-methyl-5-(methoxymethoxy)-1-(methoxycarbonyl)-2-piperidyl]acetate 在 lithium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Construction of 4a,8a-cis-octahydroquinolin-7-one core using an intramolecular aldol type of cyclization: An application to enantioselective total synthesis of lepadin B

  摘要：

  An intramolecular aldol type of cyclization of the piperidine derivative 1 proceeded in highly stereoselective manner to afford the desired 4a,8a-cis-octahydroquinolin-7-one. This key step involves a feature of the use of A((1,3)) strain as a control element, in biasing 1 towards the conformer desired for the above cyclization. An application of this aldol reaction to enantioselective total synthesis of the marine alkaloid lepadin B is also described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00603-1
• 作为产物：
  描述：

  methyl 6-methyl-5-(methoxymethoxy)-2-oxopiperidinecarboxylate 在 copper(l) iodide 、 四(三苯基膦)钯 、 甲基锂 、 三乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 2-[3-vinyl-6-methyl-5-(methoxymethoxy)-1-(methoxycarbonyl)-2-piperidyl]acetate
  参考文献：
  名称：

  Construction of 4a,8a-cis-octahydroquinolin-7-one core using an intramolecular aldol type of cyclization: An application to enantioselective total synthesis of lepadin B

  摘要：

  An intramolecular aldol type of cyclization of the piperidine derivative 1 proceeded in highly stereoselective manner to afford the desired 4a,8a-cis-octahydroquinolin-7-one. This key step involves a feature of the use of A((1,3)) strain as a control element, in biasing 1 towards the conformer desired for the above cyclization. An application of this aldol reaction to enantioselective total synthesis of the marine alkaloid lepadin B is also described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00603-1

文献信息

• Enantioselective Total Synthesis of the Marine Alkaloid Lepadin B
  作者：Naoki Toyooka、Maiko Okumura、Hiroki Takahata

  DOI：10.1021/jo990141n

  日期：1999.4.1
• Construction of 4a,8a-cis-octahydroquinolin-7-one core using an intramolecular aldol type of cyclization: An application to enantioselective total synthesis of lepadin B
  作者：Naoki Toyooka、Maiko Okumura、Hiroki Takahata、Hideo Nemoto

  DOI：10.1016/s0040-4020(99)00603-1

  日期：1999.8

  An intramolecular aldol type of cyclization of the piperidine derivative 1 proceeded in highly stereoselective manner to afford the desired 4a,8a-cis-octahydroquinolin-7-one. This key step involves a feature of the use of A((1,3)) strain as a control element, in biasing 1 towards the conformer desired for the above cyclization. An application of this aldol reaction to enantioselective total synthesis of the marine alkaloid lepadin B is also described. (C) 1999 Elsevier Science Ltd. All rights reserved.