(9R,9aS)-9-Hydroxy-5,8,9,9a-tetrahydro-1H-oxazolo[3,4-a]azepin-3-one | 357205-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: (9R,9aS)-9-Hydroxy-5,8,9,9a-tetrahydro-1H-oxazolo[3,4-a]azepin-3-one
• 英文别名: (9R,9aS)-9-hydroxy-5,8,9,9a-tetrahydro-1H-[1,3]oxazolo[3,4-a]azepin-3-one
• CAS: 357205-62-0
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: HKHGXQGMDOBVKH-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9R,9aS)-9-Hydroxy-5,8,9,9a-tetrahydro-1H-oxazolo[3,4-a]azepin-3-one 在 吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 7.0h， 生成 (6S,7R,9R,9aS)-6,7-bis(acetyloxy)-3-oxohexahydro-1H-[1,3]oxazolo[3,4-a]azepin-9-yl acetate
  参考文献：
  名称：

  Versatile approach for the synthesis of novel seven-membered iminocyclitols via ring-closing metathesis dihydroxylation reaction

  摘要：

  Seven-membered iminocyclitols with diverse diastereomers were prepared starting with D- and L-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive inhibitor for beta-glucosidase with K-i 26.3 muM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.064
• 作为产物：
  描述：

  methyl (4S)-2-oxo-3-prop-2-enyl-1,3-oxazolidine-4-carboxylate 在 sodium tetrahydroborate 、 Grubbs catalyst first generation 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (9R,9aS)-9-Hydroxy-5,8,9,9a-tetrahydro-1H-oxazolo[3,4-a]azepin-3-one
  参考文献：
  名称：

  通过闭环烯烃复分解合成恶唑烷二氮杂环化合物：脱氧天竺葵和羟基吡咯烷核苷合成的实际入口

  摘要：

  从d-和l-丝氨酸开始，说明了一种制备恶唑烷二基哌啶，氮杂环庚烷和氮杂环辛烯的简便方法，作为通往各种脱氧天竺葵和羟基吡咯烷核苷的途径。恶唑烷基二烯烃的闭环烯烃复分解用作构建氮杂环的关键步骤。恶唑烷二基氮杂环辛烯的连续环氧化，水解和环过环生成羟基吡咯烷核苷。

  DOI：

  10.1016/s0040-4039(01)00635-9

文献信息

• Synthesis of oxazolidinyl azacycles via ring-closing olefin metathesis: a practical entry to the synthesis of deoxy-azasugars and hydroxypyrrolizidines
  作者：Thangaiah Subramanian、Chang-Ching Lin、Chun-Cheng Lin

  DOI：10.1016/s0040-4039(01)00635-9

  日期：2001.6

  l-serines, an expedient method for the preparation of oxazolidinyl piperidines, azepenes and azacyclooctenes was illustrated as a route to various deoxy-azasugars and hydroxypyrrolizidines. The ring-closing olefin metathesis of oxazolidinyl di-olefins was used as a key-step to construct the azacycles. Consecutive epoxidation, hydrolysis and transannulation of oxazolidinyl azacyclooctene led to hydroxypyrrolizidines

  从d-和l-丝氨酸开始，说明了一种制备恶唑烷二基哌啶，氮杂环庚烷和氮杂环辛烯的简便方法，作为通往各种脱氧天竺葵和羟基吡咯烷核苷的途径。恶唑烷基二烯烃的闭环烯烃复分解用作构建氮杂环的关键步骤。恶唑烷二基氮杂环辛烯的连续环氧化，水解和环过环生成羟基吡咯烷核苷。
• Versatile approach for the synthesis of novel seven-membered iminocyclitols via ring-closing metathesis dihydroxylation reaction
  作者：Chang-Ching Lin、Yi-shin Pan、Laxmikant N Patkar、Hsiu-Mei Lin、Der-Lii M Tzou、Thangaiah Subramanian、Chun-Cheng Lin

  DOI：10.1016/j.bmc.2004.03.064

  日期：2004.6

  Seven-membered iminocyclitols with diverse diastereomers were prepared starting with D- and L-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive inhibitor for beta-glucosidase with K-i 26.3 muM. (C) 2004 Elsevier Ltd. All rights reserved.