3-Acetyl-3-allyl-4-but-3-enyl-4,5-dihydro-3H-benzo[f][1,4]oxazepin-2-one | 406725-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-Acetyl-3-allyl-4-but-3-enyl-4,5-dihydro-3H-benzo[f][1,4]oxazepin-2-one
• 英文别名: 3-acetyl-4-but-3-enyl-3-prop-2-enyl-5H-1,4-benzoxazepin-2-one
• CAS: 406725-68-6
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: LHQXESDGBHSARL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Acetyl-3-allyl-4-but-3-enyl-4,5-dihydro-3H-benzo[f][1,4]oxazepin-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以87%的产率得到11-Acetyl-9-oxa-1-azatricyclo[9.5.0.03,8]hexadeca-3,5,7,13-tetraen-10-one
  参考文献：
  名称：

  Synthesis of Novel α-Substituted and α,α-Disubstituted Amino Acids by Rearrangement of Ammonium Ylides Generated from Metal Carbenoids

  摘要：

  [GRAPHICS]A new and general four-step synthesis of protected alpha-substituted and alpha,alpha-disubstituted amino acids has been developed. The key step involves intramolecular ammonium ylide generation from a copper carbenoid with concomitant [2,3] rearrangement. The aromatic template serves as a tether, protecting group, and activating group for peptide coupling. The ylide rearrangement products can be converted into protected cyclic amino acids by ring-closing metathesis.

  DOI：

  10.1021/ol017240j
• 作为产物：
  描述：

  2-[[But-3-enyl(prop-2-enyl)amino]methyl]phenol 在 六氟乙酰丙酮化铜的水合物 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 、 苯 为溶剂， 生成 3-Acetyl-3-allyl-4-but-3-enyl-4,5-dihydro-3H-benzo[f][1,4]oxazepin-2-one
  参考文献：
  名称：

  Synthesis of Novel α-Substituted and α,α-Disubstituted Amino Acids by Rearrangement of Ammonium Ylides Generated from Metal Carbenoids

  摘要：

  [GRAPHICS]A new and general four-step synthesis of protected alpha-substituted and alpha,alpha-disubstituted amino acids has been developed. The key step involves intramolecular ammonium ylide generation from a copper carbenoid with concomitant [2,3] rearrangement. The aromatic template serves as a tether, protecting group, and activating group for peptide coupling. The ylide rearrangement products can be converted into protected cyclic amino acids by ring-closing metathesis.

  DOI：

  10.1021/ol017240j

文献信息

• Synthesis of Novel α-Substituted and α,α-Disubstituted Amino Acids by Rearrangement of Ammonium Ylides Generated from Metal Carbenoids
  作者：J. Stephen Clark、Mark D. Middleton

  DOI：10.1021/ol017240j

  日期：2002.3.1

  [GRAPHICS]A new and general four-step synthesis of protected alpha-substituted and alpha,alpha-disubstituted amino acids has been developed. The key step involves intramolecular ammonium ylide generation from a copper carbenoid with concomitant [2,3] rearrangement. The aromatic template serves as a tether, protecting group, and activating group for peptide coupling. The ylide rearrangement products can be converted into protected cyclic amino acids by ring-closing metathesis.