4--3-formyl-2(2H)-chromenone | 154417-80-8

• 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: 4--3-formyl-2(2H)-chromenone
• 英文别名: 6-(N-benzyl-(E)-cynnamylamino)-3-formyl[1]benzopyran-2(2H)-one；4-[N-benzyl-(trans-cinnamyl)amino]-3-formyl-2(2H)-chromenone；4-[benzyl-[(E)-3-phenylprop-2-enyl]amino]-2-oxochromene-3-carbaldehyde
• CAS: 154417-80-8
• 化学式: C₂₆H₂₁NO₃
• 分子量: 395.458
• InChiKey: GPUKGTACXIRBFJ-NTEUORMPSA-N

物化性质

• 沸点：
  682.3±55.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4--3-formyl-2(2H)-chromenone 以 甲苯 为溶剂， 反应 12.0h， 以64%的产率得到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
• 作为产物：
  描述：

  4-氯-3-甲酰基香豆素 、 苄基-((E)-3-苯基-烯丙基)-胺 生成 4--3-formyl-2(2H)-chromenone
  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

• Competitive thermal ene reaction and Diels–Alder reactions of 2-[N-(alk-2-enyl)benzylamino]-3-vinylpyrido[1,2-a]pyrimidin-4(4H)-ones
  作者：Michihiko Noguchi、Toshiya Sunagawa、Ryosuke Akao、Hisashi Yamada、Hidetoshi Yamamoto、Akikazu Kakehi

  DOI：10.1016/j.tet.2007.03.037

  日期：2007.5

  Thermal reaction of 2-[N-(alk-2-enyl)benzylamino]-3-(2-substituted and 2,2-disubstituted)vinylpyrido[1,2-a]pyrimidin-4(4H)-ones gave azepine, the desired ene products, and/or pyran derivatives. The formation of the latter was responsible for the [4+2] cycloaddition reaction between the α,β-unsaturated ester carbonyl moiety as a diene part and the alkenylamino moiety as an ene one. The reaction features

  2- [ N-（烷-2-烯基）苄氨基] -3-（2-取代和2,2-二取代）乙烯基吡啶并[1,2 - a ]嘧啶-4（4 H）-的热反应得到氮杂gave ，所需的烯产物和/或吡喃衍生物。后者的形成负责作为二烯部分的α，β-不饱和酯羰基部分与作为烯基的烯基氨基部分之间的[4 + 2]环加成反应。反应特征取决于乙烯基和链烯基对应物上的取代基的种类。乙烯基部分上的强吸电子取代基或烯基上的供电子取代基将反应特征从烯反应转变为杂狄尔斯-阿尔德反应。
• Gotoh, Mitsuhiro; Mizui, Takahiro; Sun, Bin, Journal of the Chemical Society. Perkin transactions I, 1995, # 14, p. 1857 - 1862
  作者：Gotoh, Mitsuhiro、Mizui, Takahiro、Sun, Bin、Hirayama, Ken、Noguchi, Michihiko

  DOI：——

  日期：——
• 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.