(3S,11bR)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one | 949463-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (3S,11bR)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one
• 英文别名: (3S,11bR)-3-amino-9,11-bis(phenylmethoxy)-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one
• CAS: 949463-54-1
• 化学式: C₂₇H₂₈N₂O₃
• 分子量: 428.531
• InChiKey: IGNPLGRMUYDVSF-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,11bR)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one 在 palladium on activated charcoal 三甲基氯硅烷 、 氢气 、 三氧化硫吡啶 、 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 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 49.0h， 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 31.5h， 生成 (3S,11bR)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one
  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

• Asymmetric formal synthesis of schulzeines A and C
  作者：Jaebong Jang、Jong-Wha Jung、Jaeseung Ahn、Jaehoon Sim、Dong-Jo Chang、Dae-Duk Kim、Young-Ger Suh

  DOI：10.1039/c2ob25772f

  日期：——

  The asymmetric formal synthesis of schulzeines A and C is described. Key features of the synthesis include the efficient and stereoselective construction of the benzoquinolizidine skeleton via the aza-Claisen rearrangement-induced ring expansion of the 1-vinyl-N-glycyl-isoquinoline, which was prepared by the highly enantioselective asymmetric allylation of the 8-benzyloxy-substituted dihydroisoquinoline and by the acid-catalyzed transannulation of the resulting 10-membered lactam.

  描述了舒尔泽因A和C的不对称形式合成。合成的关键特征包括通过氮-Claisen重排诱导的环扩展有效且立体选择性地构建苯并喹啉啶骨架，该反应是通过对8-苄氧取代的二氢喹啉进行高选择性的非对称烯丙基化以及对所得10元内酯进行酸催化的环转化反应得到的。
• Formal synthesis of schulzeines B and C
  作者：Punlop Kuntiyong、Sunisa Akkarasamiyo、Nuanpan Piboonsrinakara、Chitlada Hemmara、Poramate Songthammawat

  DOI：10.1016/j.tet.2011.07.085

  日期：2011.10

  A formal synthesis of schulzeines B and C, marine natural products with inhibitory effect against α-glucosidase, has been achieved. The key reactions of the synthesis are N-acyliminium ion cyclization, Sharpless asymmetric dihydroxylation, olefin cross metathesis, and asymmetric allylboration.

  已经完成了具有舒张作用的B和C的合成，这是一种对α-葡萄糖苷酶具有抑制作用的海洋天然产物。合成的关键反应是N-酰基亚胺离子环化，Sharpless不对称二羟基化，烯烃交叉复分解和不对称烯丙基硼化。
• Bowen, Edward G.; Wardrop, Duncan J., Journal of the American Chemical Society, 2009, vol. 131, p. 6062 - 6063
  作者：Bowen, Edward G.、Wardrop, Duncan J.

  DOI：——

  日期：——
• Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde
  作者：Gang Liu、Daniel Romo

  DOI：10.1021/ol802992m

  日期：2009.3.5

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.