(1S,3S,4S,6S,8S,9S,12S)-9-[3-azidopropyl]-6-methoxy-12-methyl-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one | 1274891-87-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,3S,4S,6S,8S,9S,12S)-9-[3-azidopropyl]-6-methoxy-12-methyl-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one
• 英文别名: (2S,3S,5S,6aS,7S,10S,10aR)-7-(3-azidopropyl)-5-methoxy-10-methyl-2,3-diphenyl-3,5,6,6a,7,9,10,10a-octahydro-2H-benzo[e][1,4]dioxocin-8-one
• CAS: 1274891-87-0
• 化学式: C₂₇H₃₃N₃O₄
• 分子量: 463.577
• InChiKey: COEQJOOINTXPMO-ITPTVPIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,6S,8S,9S,12S)-9-[3-azidopropyl]-6-methoxy-12-methyl-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one 在 盐酸 、 甲醇 、 水 、 戴斯-马丁氧化剂 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 103.0h， 生成 (4aR,5S,8S,8aR,10S,11R)-8-(3-methoxypropyl)-10-methyl-11-(2-oxo-1,2-diphenylethoxy)hexahydro-1H-5,8a-propanoquinoline-7(8H)-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Clavolonine

  摘要：

  The asymmetric total synthesis of clavolonine (1) has been achieved based on chiral auxiliary multiple-use methodology. Our synthetic route features stereoselective transformations on the cyclohexane ring utilizing the steric environment of the chiral auxiliary and an intramolecular Mannich reaction to construct the fused ring system.

  DOI：

  10.1021/ol200376z
• 作为产物：
  描述：

  (2S,3S,5S,6aS,7S,10S,10aR)-7-(3-chloropropyl)-5-methoxy-10-methyl-2,3-diphenyl-3,5,6,6a,7,9,10,10a-octahydro-2H-benzo[e][1,4]dioxocin-8-one 在 sodium azide 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以124 mg的产率得到(1S,3S,4S,6S,8S,9S,12S)-9-[3-azidopropyl]-6-methoxy-12-methyl-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Clavolonine

  摘要：

  The asymmetric total synthesis of clavolonine (1) has been achieved based on chiral auxiliary multiple-use methodology. Our synthetic route features stereoselective transformations on the cyclohexane ring utilizing the steric environment of the chiral auxiliary and an intramolecular Mannich reaction to construct the fused ring system.

  DOI：

  10.1021/ol200376z

文献信息

• Asymmetric Total Synthesis of Clavolonine
  作者：Kenji Nakahara、Kie Hirano、Ryota Maehata、Yasuyuki Kita、Hiromichi Fujioka

  DOI：10.1021/ol200376z

  日期：2011.4.15

  The asymmetric total synthesis of clavolonine (1) has been achieved based on chiral auxiliary multiple-use methodology. Our synthetic route features stereoselective transformations on the cyclohexane ring utilizing the steric environment of the chiral auxiliary and an intramolecular Mannich reaction to construct the fused ring system.