4-cyclopropylmethylene-2-phenyl-4H-oxazol-5-one | 200482-55-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-cyclopropylmethylene-2-phenyl-4H-oxazol-5-one
• 英文别名: (4Z)-4-(Cyclopropylmethylene)-2-phenyl-5(4H)-oxazolone；(4Z)-4-(cyclopropylmethylidene)-2-phenyl-1,3-oxazol-5-one
• CAS: 200482-55-9
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: JXVUUGXJFXLTLG-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyclopropylmethylene-2-phenyl-4H-oxazol-5-one 在 palladium on activated charcoal 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 甲烷磺酸 、 BoPhoz 、 氢气 、 sodium methylate 、 一水合肼 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 3.0~50.0 ℃ 、310.26 kPa 条件下， 反应 30.0h， 生成 L-环丙基丙氨酸
  参考文献：
  名称：

  The preparation of enantiomerically pure cyclopropylalanine

  摘要：

  Single enantiomer cyclopropylalanine (>99.9% ee) and various derivatives were prepared using an asymmetric hydrogenation approach with a rhodium catalyst based on the methyl BoPhox(TM) ligand. N-Boc cyclopropylalanine benzyl ester was the preferred derivative, as this material is ripe for further selective reaction and can be recrystallized to >99.5%, enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.007
• 作为产物：
  描述：

  马尿酸 、 乙酸酐 、 环丙甲醛 在 sodium acetate 作用下， 反应 1.5h， 以33%的产率得到4-cyclopropylmethylene-2-phenyl-4H-oxazol-5-one
  参考文献：
  名称：

  The preparation of enantiomerically pure cyclopropylalanine

  摘要：

  Single enantiomer cyclopropylalanine (>99.9% ee) and various derivatives were prepared using an asymmetric hydrogenation approach with a rhodium catalyst based on the methyl BoPhox(TM) ligand. N-Boc cyclopropylalanine benzyl ester was the preferred derivative, as this material is ripe for further selective reaction and can be recrystallized to >99.5%, enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.007

文献信息

• The preparation of enantiomerically pure cyclopropylalanine
  作者：Neil W. Boaz、Sheryl D. Debenham、Shannon E. Large、Mary K. Moore

  DOI：10.1016/j.tetasy.2003.07.007

  日期：2003.11

  Single enantiomer cyclopropylalanine (>99.9% ee) and various derivatives were prepared using an asymmetric hydrogenation approach with a rhodium catalyst based on the methyl BoPhox(TM) ligand. N-Boc cyclopropylalanine benzyl ester was the preferred derivative, as this material is ripe for further selective reaction and can be recrystallized to >99.5%, enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.