(S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide | 949463-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide
• 英文别名: (14S)-N-[(3S,11bR)-4-oxo-9,11-bis(phenylmethoxy)-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-3-yl]-16-[(4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-14-(methoxymethoxy)hexadecanamide
• CAS: 949463-71-2
• 化学式: C₆₀H₉₀N₂O₈
• 分子量: 967.383
• InChiKey: RIVQKTYQQIJRJG-APOQZGTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.4
• 重原子数：
  70
• 可旋转键数：
  35
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide 在 三甲基氯硅烷 、 三氧化硫吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.0h， 生成 schulzeine C
  参考文献：
  名称：

  Total Syntheses of Schulzeines B and C

  摘要：

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.

  DOI：

  10.1021/jo070560h
• 作为产物：
  描述：

  Z-L-GluOMe 在 palladium on activated charcoal 盐酸 、 氢气 、 四丁基碘化铵 、 sodium cyanoborohydride 、 碳酸氢钠 、 caesium carbonate 、 溶剂黄146 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 生成 (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide
  参考文献：
  名称：

  Total Syntheses of Schulzeines B and C

  摘要：

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.

  DOI：

  10.1021/jo070560h

文献信息

• Total Syntheses of Schulzeines B and C
  作者：Mukund K. Gurjar、Chinmoy Pramanik、Debabrata Bhattasali、C. V. Ramana、Debendra K. Mohapatra

  DOI：10.1021/jo070560h

  日期：2007.8.1

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.