(4S)-3-烯丙基-2-氧代-1,3-恶唑烷-4-甲醛 | 340256-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (4S)-3-烯丙基-2-氧代-1,3-恶唑烷-4-甲醛
• 英文名称: (S)-3-Allyl-2-oxo-oxazolidine-4-carbaldehyde
• 英文别名: (4S)-2-oxo-3-prop-2-enyl-1,3-oxazolidine-4-carbaldehyde
• CAS: 340256-53-3
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: XPQWLONHPRDMMW-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-3-烯丙基-2-氧代-1,3-恶唑烷-4-甲醛 在 Grubbs catalyst first generation 吡啶 、 氢氧化钾 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 30.0h， 生成 (3R,4S,6S,7S)-7-Hydroxymethyl-azepane-3,4,6-triol
  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 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4S)-3-烯丙基-2-氧代-1,3-恶唑烷-4-甲醛
  参考文献：
  名称：

  Microwave-induced 1,3-dipolar intramolecular cycloadditions of N-substituted oximes, nitrones, and azomethine ylides for the chiral synthesis of functionalized nitrogen heterocycles

  摘要：

  在硅胶表面，在不使用溶剂的情况下，在微波辐射下，对不饱和N-取代肟、硝酮和氮丙啶亚基进行高度立体选择性分子内环加成，从而以高收率生产出与吡咯啉或哌啶环融合的官能化三环异噁唑烷。

  DOI：

  10.1039/b006000n

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。
• Microwave-induced 1,3-dipolar intramolecular cycloadditions of N-substituted oximes, nitrones, and azomethine ylides for the chiral synthesis of functionalized nitrogen heterocycles
  作者：Qian Cheng、Wen Zhang、Yoshimichi Tagami、Takayuki Oritani

  DOI：10.1039/b006000n

  日期：——

  Highly stereoselective intramolecular cycloadditions of unsaturated N-substituted oximes, nitrones, and azomethine ylides on the surface of silica gel without a solvent, which have been conducted under microwave irradiation, to produce functionalized tricyclic isoxazolidines fused with a pyrroline or piperidine ring in good yields, are presented.

  在硅胶表面，在不使用溶剂的情况下，在微波辐射下，对不饱和N-取代肟、硝酮和氮丙啶亚基进行高度立体选择性分子内环加成，从而以高收率生产出与吡咯啉或哌啶环融合的官能化三环异噁唑烷。
• 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.