(3aR,7R,7aR)-4-hydroxy-7-methoxyspiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,1'-cyclopentane]-2-one | 297754-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aR,7R,7aR)-4-hydroxy-7-methoxyspiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,1'-cyclopentane]-2-one
• CAS: 297754-66-6
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: XPDDULJOISHWJY-VCWZQCKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,7R,7aR)-4-hydroxy-7-methoxyspiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,1'-cyclopentane]-2-one 在 palladium on activated charcoal 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Improved antibacterial activities of coumarin antibiotics bearing 5′,5′-dialkylnoviose: biological activity of RU79115

  摘要：

  A new series of coumarin inhibitors of DNA gyrase B bearing a N-propargyloxycarbamate at C-3' of various 5',5'-dialkylnoviose, including RU79115, were synthesised and their antibacterial activities have been delineated. Introduction of dialkyl substituents at 5'5'-position of noviose leads to coumarin analogues with improved in vitro and in vivo antibacterial activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00304-8
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 [8R-(8α,9.alpha,10.beta)]-10-methoxy-6-oxaspiro[4.5]decan-7,8,9-triol 以 1,2-二氯乙烷 为溶剂， 以67%的产率得到(3aR,7R,7aR)-4-hydroxy-7-methoxyspiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,1'-cyclopentane]-2-one
  参考文献：
  名称：

  Improved antibacterial activities of coumarin antibiotics bearing 5′,5′-dialkylnoviose: biological activity of RU79115

  摘要：

  A new series of coumarin inhibitors of DNA gyrase B bearing a N-propargyloxycarbamate at C-3' of various 5',5'-dialkylnoviose, including RU79115, were synthesised and their antibacterial activities have been delineated. Introduction of dialkyl substituents at 5'5'-position of noviose leads to coumarin analogues with improved in vitro and in vivo antibacterial activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00304-8

文献信息

• Improved antibacterial activities of coumarin antibiotics bearing 5′,5′-dialkylnoviose: biological activity of RU79115
  作者：Branislav Musicki、Anne-Marie Periers、Patrick Laurin、Didier Ferroud、Yannick Benedetti、Sylvette Lachaud、Fabienne Chatreaux、Jean-Luc Haesslein、Alain Iltis、Christine Pierre、Jean Khider、Nicole Tessot、Marlene Airault、Jacques Demassey、Claudine Dupuis-Hamelin、Patrice Lassaigne、Alain Bonnefoy、Pascale Vicat、Michel Klich

  DOI：10.1016/s0960-894x(00)00304-8

  日期：2000.8

  A new series of coumarin inhibitors of DNA gyrase B bearing a N-propargyloxycarbamate at C-3' of various 5',5'-dialkylnoviose, including RU79115, were synthesised and their antibacterial activities have been delineated. Introduction of dialkyl substituents at 5'5'-position of noviose leads to coumarin analogues with improved in vitro and in vivo antibacterial activity. (C) 2000 Elsevier Science Ltd. All rights reserved.