1-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-trimethylsilyloxy-3-aza-4-phenylbuta-1Z,3E-diene | 350045-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-trimethylsilyloxy-3-aza-4-phenylbuta-1Z,3E-diene
• 英文别名: (4S)-3-[(Z)-2-[(E)-benzylideneamino]-2-trimethylsilyloxyethenyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 350045-02-2
• 化学式: C₂₁H₂₄N₂O₃Si
• 分子量: 380.519
• InChiKey: HQDVKOCIYFFYFR-JGOWVBOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-trimethylsilyloxy-3-aza-4-phenylbuta-1Z,3E-diene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以32%的产率得到(4S)-3-[(3S,4S)-2-oxo-4-phenyl-azetidin-3-yl]-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Lewis acid-catalyzed electrocyclization of 2-aza-1,3-butadienes to NH-β-lactams

  摘要：

  Lewis acid-catalyzed cyclization of 2-aza-3-trimethylsilytoxy-buta-1,3-diene is reported.. Stereochemical differences with the uncatalyzed cyclization are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00162-9
• 作为产物：
  描述：

  (S)-(+)-2-氧代-4-苯基-3-恶唑烷乙酸 在 草酰氯 、 三乙胺 作用下， 以 正庚烷 、 甲苯 为溶剂， 反应 1.0h， 生成 1-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-trimethylsilyloxy-3-aza-4-phenylbuta-1Z,3E-diene
  参考文献：
  名称：

  Synthesis of perhydroxazin-4-ones. Competitive Mukaiyama versus hetero Diels–Alder reaction in the cycloaddition of 2-aza-3-trimethylsilyloxy-1,3-butadiene and aldehydes

  摘要：

  The reactions of 2-aza-3-trimethylsilyloxy-1,3-butadiene with carbonyl dienophiles are described. 2-Aza-1,3-butadienes participate as dienes in the [4+2] cycloaddition with aldehydes to afford perhydroxazin-4-ones in good yields. Experimental results, however, show that a Mukaiyama type two-step reaction must be taken into account. The cycloadducts obtained have proved to be useful intermediates in the synthesis of alpha -amino-beta -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00051-9

文献信息

• Solution phase library of perhydrooxazin-4-ones
  作者：Mauro Panunzio、Marzia Villa、Andrea Missio、Tino Rossi、Pierfausto Seneci

  DOI：10.1016/s0040-4039(98)01372-0

  日期：1998.9

  A general approach to the solution phase parallel synthesis of perhydrooxazin-4-ones, which allows the preparation of milligram quantities of each individual member, is reported. An efficient purification; method, using as "Sequestration Enabling Reagent" (SER) aminomethylpolystyrene resin in the presence of trimethylorthoformate is also described. (C) 1998 Elsevier Science Ltd. All rights reserved.