(+)-5-methoxy-11-methylene-13-oxo-6-aza-tricyclo-[7.3.1.0(2,7)]trideca-2(7),3,5-triene-1-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-5-methoxy-11-methylene-13-oxo-6-aza-tricyclo-[7.3.1.0(2,7)]trideca-2(7),3,5-triene-1-carboxylic acid methyl ester
• 英文别名: methyl (1S)-5-methoxy-11-methylidene-13-oxo-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-1-carboxylate
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: KXBVNZQSMLPXLD-CSPPYYTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-5-methoxy-11-methylene-13-oxo-6-aza-tricyclo-[7.3.1.0(2,7)]trideca-2(7),3,5-triene-1-carboxylic acid methyl ester 在 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以80%的产率得到(+)-5-methoxy-11-methyl-13-oxo-6-aza-tricyclo-[7.3.1.0(2,7)]trideca-2(7),3,5,10-tetraene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Development of a Large-Scale Synthetic Route to Manufacture (−)-Huperzine A

  摘要：

  A safe, practical and scalable process for manufacture of (-)-huperzine A has been developed and scaled up to manufacture several hundred grams of (-)-huperzine A with chemical and optical purity of >99%. The process consists of 11 chemical stages starting from commercially available materials with only nine isolation steps and no chromatography purification. This process provides a reliable and cost-effective source of synthetic (-)-huperzine A and its derivatives for pharmaceutical and nutraceutical markets.

  DOI：

  10.1021/op200360b
• 作为产物：
  描述：

  7’,8’-dihydro-5’H-spiro[1,3-dioxolane-2,6’-quinoline]-2’-ol 在 bis(η3-allyl-μ-chloropalladium(II)) 、 磷酸 、 Taniaphos ligand 、 苄基三乙基氯化铵 、 sodium hydride 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 12.75h， 生成 (+)-5-methoxy-11-methylene-13-oxo-6-aza-tricyclo-[7.3.1.0(2,7)]trideca-2(7),3,5-triene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Development of a Large-Scale Synthetic Route to Manufacture (−)-Huperzine A

  摘要：

  A safe, practical and scalable process for manufacture of (-)-huperzine A has been developed and scaled up to manufacture several hundred grams of (-)-huperzine A with chemical and optical purity of >99%. The process consists of 11 chemical stages starting from commercially available materials with only nine isolation steps and no chromatography purification. This process provides a reliable and cost-effective source of synthetic (-)-huperzine A and its derivatives for pharmaceutical and nutraceutical markets.

  DOI：

  10.1021/op200360b

文献信息

• Development of a Large-Scale Synthetic Route to Manufacture (−)-Huperzine A
  作者：Stephen R. Tudhope、Julie A. Bellamy、Anthony Ball、Dewakar Rajasekar、Manouchehr Azadi-Ardakani、Harihara Subramanian Meera、Jesudoss Mercy Gnanadeepam、Ramanathan Saiganesh、Frank Gibson、Linli He、Carl H. Behrens、Gail Underiner、Judith Marfurt、Nathalie Favre

  DOI：10.1021/op200360b

  日期：2012.4.20

  A safe, practical and scalable process for manufacture of (-)-huperzine A has been developed and scaled up to manufacture several hundred grams of (-)-huperzine A with chemical and optical purity of >99%. The process consists of 11 chemical stages starting from commercially available materials with only nine isolation steps and no chromatography purification. This process provides a reliable and cost-effective source of synthetic (-)-huperzine A and its derivatives for pharmaceutical and nutraceutical markets.