(1S,3S,4S,6S,8S)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one | 1225205-29-7

• 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)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one
• 英文别名: (2S,3S,5S,6aS,10aS)-5-methoxy-2,3-diphenyl-3,5,6,6a,7,10a-hexahydro-2H-1,4-benzodioxocin-8-one
• CAS: 1225205-29-7
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: KVWWHAMAKWNCBJ-HMWDHGCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,6S,8S)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one 在 copper(l) iodide 、 sodium azide 、 水 、 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.5h， 生成 1-[(4aS,5S,6R,7S)-7-methyl-6-[(1S)-2-oxo-1,2-diphenylethoxy]-2,3,4,4a,5,6,7,8-octahydroquinolin-5-yl]-6-methoxyhexan-2-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：

  在 2,3-二甲基-2-丁基硼烷 、 pyridinium dichromate 作用下， 生成 (1S,3S,4S,6S,8S)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one
  参考文献：
  名称：

  The first asymmetric total syntheses of both enantiomers of cryptocaryone

  摘要：

  The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.101

文献信息

• The first asymmetric total syntheses of both enantiomers of cryptocaryone
  作者：Hiromichi Fujioka、Kenji Nakahara、Tomohiro Oki、Kie Hirano、Tatsuya Hayashi、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2010.01.101

  日期：2010.4

  The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.