Methanesulfonic acid (2S,3S,3aR)-2-methanesulfonyloxymethyl-2,3,3a,8-tetrahydro-1-oxa-12b-aza-dibenzo[e,h]azulen-3-ylmethyl ester | 731856-53-4

• 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: Methanesulfonic acid (2S,3S,3aR)-2-methanesulfonyloxymethyl-2,3,3a,8-tetrahydro-1-oxa-12b-aza-dibenzo[e,h]azulen-3-ylmethyl ester
• 英文别名: [(4S,5S,6R)-4-(methylsulfonyloxymethyl)-3-oxa-2-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7,9,11,14,16-hexaen-5-yl]methyl methanesulfonate
• CAS: 731856-53-4
• 化学式: C₂₀H₂₃NO₇S₂
• 分子量: 453.537
• InChiKey: NEWPTZQEMHLTRJ-SXLOBPIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2S,3S,3aR)-2-methanesulfonyloxymethyl-2,3,3a,8-tetrahydro-1-oxa-12b-aza-dibenzo[e,h]azulen-3-ylmethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 2.0h， 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 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 19.17h， 生成 Methanesulfonic acid (2S,3S,3aR)-2-methanesulfonyloxymethyl-2,3,3a,8-tetrahydro-1-oxa-12b-aza-dibenzo[e,h]azulen-3-ylmethyl ester
  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

文献信息

• 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
  作者：José L. Garcı́a Ruano、J. Ignacio Andrés Gil、Alberto Fraile、Ana Marı́a Martı́n Castro、M. Rosario Martı́n

  DOI：10.1016/j.tetlet.2004.04.108

  日期：2004.6

  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.