(S₂,S₃,R_3a)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine-2,3-diyldimethanol | 731856-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (S₂,S₃,R_3a)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine-2,3-diyldimethanol
• 英文别名: [(4S,5S,6R)-4-(hydroxymethyl)-3-oxa-2-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7,9,11,14,16-hexaen-5-yl]methanol
• CAS: 731856-48-7
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: SXEVCDGSZSZTTE-JQHSSLGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S₂,S₃,R_3a)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine-2,3-diyldimethanol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 2.17h， 生成 {2-hydroxy-2,3,9,13b-tetrahydro-1H-dibenzo[c,f]pyrrolo[2,1-a]azepin-1-yl}methylethanesulfonate
  参考文献：
  名称：

  Asymmetric 1,3-dipolar reactions of 3-sulfinylfuran-2(5 H )-ones with 11 H -dibenzo[ b,e ]azepine 5-oxide. Synthesis of pyrroloazepines via isoxazoloazepines

  摘要：

  The addition of morphanthridine N-oxide (1) to homochiral 3-p-tolylsulfinylfuran-2(5H)-ones (2a and 2b) under mild conditions affords furoisoxazoloazepines (3a and 3b) in high yields and with complete regioselectivity. The pi-facial and endo-selectivities are also complete from 2a, which yields anti-3a-endo as the only diastereoisomer, whereas cycloreversion determines that the anti-3b-endo adduct can be almost exclusively isolated from 2b. Proper manipulation of the furoisoxazoloazepines allows the synthesis of the optically pure isoxazoloazepines and pyrroloazepines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.108
• 作为产物：
  描述：

  11H-dibenzo[b,e]azepine 5-oxide 在 lithium aluminium tetrahydride 、 aluminium amalgam 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 19.0h， 生成 (S₂,S₃,R_3a)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine-2,3-diyldimethanol
  参考文献：
  名称：

  Asymmetric 1,3-dipolar reactions of 3-sulfinylfuran-2(5 H )-ones with 11 H -dibenzo[ b,e ]azepine 5-oxide. Synthesis of pyrroloazepines via isoxazoloazepines

  摘要：

  The addition of morphanthridine N-oxide (1) to homochiral 3-p-tolylsulfinylfuran-2(5H)-ones (2a and 2b) under mild conditions affords furoisoxazoloazepines (3a and 3b) in high yields and with complete regioselectivity. The pi-facial and endo-selectivities are also complete from 2a, which yields anti-3a-endo as the only diastereoisomer, whereas cycloreversion determines that the anti-3b-endo adduct can be almost exclusively isolated from 2b. Proper manipulation of the furoisoxazoloazepines allows the synthesis of the optically pure isoxazoloazepines and pyrroloazepines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.108