(4Z)-4-[[4-[2-methoxy-5-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenoxy]phenyl]methylidene]-2-phenyl-1,3-oxazol-5-one | 222054-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4Z)-4-[[4-[2-methoxy-5-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenoxy]phenyl]methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 222054-68-4
• 化学式: C₃₃H₂₂N₂O₆
• 分子量: 542.547
• InChiKey: MXERPLAOIFBTQA-WCOOBMQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,7-二氨基庚烷 、 (4Z)-4-[[4-[2-methoxy-5-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenoxy]phenyl]methylidene]-2-phenyl-1,3-oxazol-5-one 以 氯仿 为溶剂， 反应 72.0h， 以7%的产率得到N-[(8Z,21Z)-10,20-dihydroxy-9-[[hydroxy(phenyl)methylidene]amino]-4-methoxy-2-oxa-11,19-diazatricyclo[21.2.2.13,7]octacosa-1(25),3,5,7(28),8,10,19,21,23,26-decaen-21-yl]benzenecarboximidic acid
  参考文献：
  名称：

  Entropically Favorable Macrolactamization. Synthesis of Isodityrosine Peptide Analogues by Tandem Erlenmeyer Condensation−Macrolactamization

  摘要：

  Macrolactams containing a modified isodityrosine moiety were assembled by direct addition of a bis-4-aryliden-5(4H)-oxazolone, derived by double Erlenmeyer condensation of diaryl ether dicar-boxaldehydes and an alpha,omega-diamine. derived from the same precursor. Tandem acylation of diamines with the bis-Erlenmeyer oxazolone gave macrolactams in yields of up to 30%. TECM demonstrates an entropically controlled 28-membered ring closure and allows rapid access to a variety of cyclic isodityrosine peptide analogues of the biologically active natural product bastadin-5.

  DOI：

  10.1021/jo9825198
• 作为产物：
  描述：

  异香兰素 在 rubidium fluoride 、 lead acetate 、 乙酸酐 、 potassium carbonate 、 copper(II) oxide 作用下， 以 吡啶 为溶剂， 反应 36.0h， 生成 (4Z)-4-[[4-[2-methoxy-5-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenoxy]phenyl]methylidene]-2-phenyl-1,3-oxazol-5-one
  参考文献：
  名称：

  Entropically Favorable Macrolactamization. Synthesis of Isodityrosine Peptide Analogues by Tandem Erlenmeyer Condensation−Macrolactamization

  摘要：

  Macrolactams containing a modified isodityrosine moiety were assembled by direct addition of a bis-4-aryliden-5(4H)-oxazolone, derived by double Erlenmeyer condensation of diaryl ether dicar-boxaldehydes and an alpha,omega-diamine. derived from the same precursor. Tandem acylation of diamines with the bis-Erlenmeyer oxazolone gave macrolactams in yields of up to 30%. TECM demonstrates an entropically controlled 28-membered ring closure and allows rapid access to a variety of cyclic isodityrosine peptide analogues of the biologically active natural product bastadin-5.

  DOI：

  10.1021/jo9825198

文献信息

• Entropically Favorable Macrolactamization. Synthesis of Isodityrosine Peptide Analogues by Tandem Erlenmeyer Condensation−Macrolactamization
  作者：Karl L. Bailey、Tadeusz F. Molinski

  DOI：10.1021/jo9825198

  日期：1999.4.1

  Macrolactams containing a modified isodityrosine moiety were assembled by direct addition of a bis-4-aryliden-5(4H)-oxazolone, derived by double Erlenmeyer condensation of diaryl ether dicar-boxaldehydes and an alpha,omega-diamine. derived from the same precursor. Tandem acylation of diamines with the bis-Erlenmeyer oxazolone gave macrolactams in yields of up to 30%. TECM demonstrates an entropically controlled 28-membered ring closure and allows rapid access to a variety of cyclic isodityrosine peptide analogues of the biologically active natural product bastadin-5.