(1R,2R,5R,6S)-5-羟基-2-甲氧基-3-氧杂-7-氮杂双环[4.2.0]辛烷-8-酮 | 211182-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2R,5R,6S)-5-羟基-2-甲氧基-3-氧杂-7-氮杂双环[4.2.0]辛烷-8-酮
• 英文名称: (1R,2R,5R,6S)-5-hydroxy-2-methoxy-3-oxa-7-azabicyclo[4.2.0]octan-8-one
• CAS: 211182-66-0
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: MPPBCBHTLZOZOX-MEOJTODESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,5R,6S)-5-羟基-2-甲氧基-3-氧杂-7-氮杂双环[4.2.0]辛烷-8-酮 在 ruthenium(IV) oxide 、 sodium periodate 、 苄基三乙基氯化铵 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以93%的产率得到(1R,2R,6S)-2-methoxy-3-oxa-7-azabicyclo[4.2.0]octane-5,8-dione
  参考文献：
  名称：

  Formation of β-lactams fused to the pyranoid ring via the Mitsunobu reaction

  摘要：

  N-Tosyl-2-C-carbamoyl glycosides having the alpha-L-arabino- and beta-D-xylo- configuration form under Mitsunobu conditions 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-alpha-L-lyxo and beta-D-arabinopyranosides, respectively, having the beta-lactam ring fused to the pyranoid one; neither the formation of the gamma-lactam ring nor that of the 3,4-epoxide were observed. The gamma-lactam 2-C:4-N-carbonyl-2,4-dideoxy-4-N-tosylamino-beta-D-xylopyranoside can be obtained after protection of the 3-hydroxy group in the starting glycoside of alpha-L-arabino-configuration. The structure and configuration of methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-ribopyranoside and methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-erythro-pyranosid-4-ulose were proved by X-ray crystallography. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00017-2
• 作为产物：
  描述：

  L-arabinal 在 palladium on activated charcoal 盐酸 、 萘 、 氢气 、 sodium 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.42h， 生成 (1R,2R,5R,6S)-5-羟基-2-甲氧基-3-氧杂-7-氮杂双环[4.2.0]辛烷-8-酮
  参考文献：
  名称：

  Formation of β-lactams fused to the pyranoid ring via the Mitsunobu reaction

  摘要：

  N-Tosyl-2-C-carbamoyl glycosides having the alpha-L-arabino- and beta-D-xylo- configuration form under Mitsunobu conditions 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-alpha-L-lyxo and beta-D-arabinopyranosides, respectively, having the beta-lactam ring fused to the pyranoid one; neither the formation of the gamma-lactam ring nor that of the 3,4-epoxide were observed. The gamma-lactam 2-C:4-N-carbonyl-2,4-dideoxy-4-N-tosylamino-beta-D-xylopyranoside can be obtained after protection of the 3-hydroxy group in the starting glycoside of alpha-L-arabino-configuration. The structure and configuration of methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-ribopyranoside and methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-erythro-pyranosid-4-ulose were proved by X-ray crystallography. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00017-2

文献信息

• Formation of β-lactams fused to the pyranoid ring via the Mitsunobu reaction
  作者：O. Zegrocka、W. Abramski、Z. Urbańczyk-Lipkowska、M. Chmielewski

  DOI：10.1016/s0008-6215(98)00017-2

  日期：1998.2

  N-Tosyl-2-C-carbamoyl glycosides having the alpha-L-arabino- and beta-D-xylo- configuration form under Mitsunobu conditions 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-alpha-L-lyxo and beta-D-arabinopyranosides, respectively, having the beta-lactam ring fused to the pyranoid one; neither the formation of the gamma-lactam ring nor that of the 3,4-epoxide were observed. The gamma-lactam 2-C:4-N-carbonyl-2,4-dideoxy-4-N-tosylamino-beta-D-xylopyranoside can be obtained after protection of the 3-hydroxy group in the starting glycoside of alpha-L-arabino-configuration. The structure and configuration of methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-ribopyranoside and methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-erythro-pyranosid-4-ulose were proved by X-ray crystallography. (C) 1998 Elsevier Science Ltd. All rights reserved.