1-benzyl-12-phenyl-1,2-dihydro-2,4-ethanochromen<4,3-c><1,3>oxazin-5(4H,5H)-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-benzyl-12-phenyl-1,2-dihydro-2,4-ethanochromen<4,3-c><1,3>oxazin-5(4H,5H)-one
• 英文别名: 1-benzyl-12-phenyl-1,2-dihydro-2,4-ethanochromen[4,3-c][1,3]oxazin-5(4H,5H)-one；(1R,13S,15S)-12-benzyl-15-phenyl-4,16-dioxa-12-azatetracyclo[11.2.1.02,11.05,10]hexadeca-2(11),5,7,9-tetraen-3-one
• 化学式: C₂₆H₂₁NO₃
• 分子量: 395.458
• InChiKey: AFQYHSAWTXGWIY-UWDQQESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯-3-甲酰基香豆素 以 甲苯 为溶剂， 反应 12.0h， 生成 1-benzyl-12-phenyl-1,2-dihydro-2,4-ethanochromen<4,3-c><1,3>oxazin-5(4H,5H)-one
  参考文献：
  名称：

  Thermal ene reaction of 4-(2-alkenylamino)-3-formyl-2(2H)-chromenones

  摘要：

  Intramolecular ene reaction of 4-(2-alkenylamino)-3-formyl-2(2H)-chromenones 7 involving carbonyl enophile proceeded stereoselectively to afford 5-hydroxychromen[3,4-b]-azepines 14. The intramolecular nucleophilic attack of hydroxy group to the enemine moiety in 14 gave 1,2-dihydro-2,4-ethanochromen[4,3-d][1,3]oxazin-5(4H,5H)-one derivatives 13 as final products. PM3 MO calculations of the process reveal that this ene reaction proceeds with two steps through an intermediate.

  DOI：

  10.1016/s0040-4020(01)80817-6

文献信息

• Thermal ene reaction of 4-(2-alkenylamino)-3-formyl-2(2H)-chromenones
  作者：Yoshiaki Kuroki、Ryosuke Akao、Tomonori Inazumi、Michihiko Noguchi

  DOI：10.1016/s0040-4020(01)80817-6

  日期：1994.1

  Intramolecular ene reaction of 4-(2-alkenylamino)-3-formyl-2(2H)-chromenones 7 involving carbonyl enophile proceeded stereoselectively to afford 5-hydroxychromen[3,4-b]-azepines 14. The intramolecular nucleophilic attack of hydroxy group to the enemine moiety in 14 gave 1,2-dihydro-2,4-ethanochromen[4,3-d][1,3]oxazin-5(4H,5H)-one derivatives 13 as final products. PM3 MO calculations of the process reveal that this ene reaction proceeds with two steps through an intermediate.