(7aR,11S,13S)-7a,8,10,11-tetrahydro-11-methyl-13-phenyl-9H,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine | 848302-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (7aR,11S,13S)-7a,8,10,11-tetrahydro-11-methyl-13-phenyl-9H,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine
• 英文别名: (12R,16S,18S)-16-methyl-18-phenyl-11-oxa-17-azatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2,4,6,8-pentaene
• CAS: 848302-36-3
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: PANJTFCEJAVGJS-YTJPUZGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7aR,11S,13S)-7a,8,10,11-tetrahydro-11-methyl-13-phenyl-9H,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine 在 palladium on activated charcoal 二氯甲烷 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 (2S,6R)-isosolenopsin hydrochloride
  参考文献：
  名称：

  Nonracemic Betti Base as a New Chiral Auxiliary:  Application to Total Syntheses of Enantiopure (2S,6R)-Dihydropinidine and (2S,6R)-Isosolenopsins

  摘要：

  Total syntheses of enantiopure alkaloidal natural products (2S,6R)-dihydropinidine (as hydrochloride) and (2S,6R)isosolenopsins (as hydrochlorides) were achieved in four steps and in 80-82% total yields by using a synthetic strategy of the formation-cleavage of 1,3-oxazinane. (S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH2Cl2.

  DOI：

  10.1021/jo0480444
• 作为产物：
  描述：

  甲基氯化镁 、 (7aR,11R,13S)-11-(1H-benzotriazol-1-yl)-7a,8,10,11-tetrahydro-13-phenyl-9H,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(7aR,11S,13S)-7a,8,10,11-tetrahydro-11-methyl-13-phenyl-9H,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine
  参考文献：
  名称：

  Nonracemic Betti Base as a New Chiral Auxiliary:  Application to Total Syntheses of Enantiopure (2S,6R)-Dihydropinidine and (2S,6R)-Isosolenopsins

  摘要：

  Total syntheses of enantiopure alkaloidal natural products (2S,6R)-dihydropinidine (as hydrochloride) and (2S,6R)isosolenopsins (as hydrochlorides) were achieved in four steps and in 80-82% total yields by using a synthetic strategy of the formation-cleavage of 1,3-oxazinane. (S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH2Cl2.

  DOI：

  10.1021/jo0480444

文献信息

• Nonracemic Betti Base as a New Chiral Auxiliary:  Application to Total Syntheses of Enantiopure (2<i>S</i>,6<i>R</i>)-Dihydropinidine and (2<i>S</i>,6<i>R</i>)-Isosolenopsins
  作者：Xinyan Wang、Yanmei Dong、Jianwei Sun、Xuenong Xu、Rui Li、Yuefei Hu

  DOI：10.1021/jo0480444

  日期：2005.3.1

  Total syntheses of enantiopure alkaloidal natural products (2S,6R)-dihydropinidine (as hydrochloride) and (2S,6R)isosolenopsins (as hydrochlorides) were achieved in four steps and in 80-82% total yields by using a synthetic strategy of the formation-cleavage of 1,3-oxazinane. (S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH2Cl2.