ethyl (E)-4-[4-chloro-2-(hydroxymethyl)anilino]-4-oxobut-2-enoate | 203917-23-1

• 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: ethyl (E)-4-[4-chloro-2-(hydroxymethyl)anilino]-4-oxobut-2-enoate
• CAS: 203917-23-1
• 化学式: C₁₃H₁₄ClNO₄
• 分子量: 283.711
• InChiKey: VPYCLJMNHNIHPJ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-4-[4-chloro-2-(hydroxymethyl)anilino]-4-oxobut-2-enoate 以 甲苯 为溶剂， 反应 24.0h， 生成 methyl 10-chloro-5-(2-ethoxy-2-oxoethyl)-6-oxo-2,5,7,11b-tetrahydro-1H-[1,2]oxazolo[2,3-d][1,4]benzodiazepine-1-carboxylate
  参考文献：
  名称：

  The synthesis of 1,2,7,11b-Tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5H)-ones

  摘要：

  The reaction of various ethyl 3-[[2-(1-hydroxyiminoalkyl)phenyl]carbamoyl]acrylates (2) with electron deficient olefins proceeds via a sequential dipole formation, dipolar cycloaddition sequence to furnish the tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and tetrahydroisoxazolo[4,3-c]quinolin-4(5H) (4) and (6). The product distribution reflects the nature of the reacting olefin and the position and extent of substitution on the acrylate moiety.

  DOI：

  10.1016/0040-4039(95)01523-x
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸 生成 ethyl (E)-4-[4-chloro-2-(hydroxymethyl)anilino]-4-oxobut-2-enoate
  参考文献：
  名称：

  The synthesis of 1,2,7,11b-Tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5H)-ones

  摘要：

  The reaction of various ethyl 3-[[2-(1-hydroxyiminoalkyl)phenyl]carbamoyl]acrylates (2) with electron deficient olefins proceeds via a sequential dipole formation, dipolar cycloaddition sequence to furnish the tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and tetrahydroisoxazolo[4,3-c]quinolin-4(5H) (4) and (6). The product distribution reflects the nature of the reacting olefin and the position and extent of substitution on the acrylate moiety.

  DOI：

  10.1016/0040-4039(95)01523-x

文献信息

• Steric control of reactivity: formation of oximes, benzodiazepinone N-oxides and isoxazoloquinolinones
  作者：Frances Heaney、Sharon Bourke、Desmond Cunningham、Patrick McArdle

  DOI：10.1039/a707857i

  日期：——

  Reaction of the alkenyl carbonyl compounds 1 with hydroxylamine can lead to the formation of the oximes 2, the benzodiazepinone N-oxides 3 or the isoxazoloquinolinones 5. The product(s) of reaction are shown to depend on the electronic nature of the terminal olefinic substituent R3 and the space filling capacity of the substituents R1, R2 and R4. When the olefinic centre is electron poor (R3 = CO2Et) ketocarbonyls convert exclusively to bicyclic nitrones 3 whereas aldehydes are more sensitive to subtle changes in skeletal structure and give rise to oximes 2, tricycles 5 or mixtures of both. For aldehyde and ketone substrates when the olefinic centre carries an aryl substituent (R3 = Ph) the primary product of reaction is the corresponding oxime which on thermal activation converts to the tricyclic isoxazoloquinolinones.

  与氢氧胺反应的烯烃羰基化合物1可以形成肟2、苯二氮杂类N-氧化物3或异噁唑喹啉酮5。反应的产物取决于末端烯烃取代基R3的电子性质，以及取代基R1、R2和R4的空间填充能力。当烯烃中心电子贫乏（R3 = CO2Et）时，酮羰基化合物仅能转化为双环硝酮3，而醛对骨架结构的微小变化更加敏感，能够生成肟2、三环化合物5或两者的混合物。对于醛和酮底物，当烯烃中心带有芳基取代基（R3 = Ph）时，反应的主要产物是相应的肟，经过热激活后转化为三环异噁唑喹啉酮。
• The synthesis of 1,2,7,11b-Tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5H)-ones
  作者：Sharon Bourke、Frances Heaney

  DOI：10.1016/0040-4039(95)01523-x

  日期：1995.10

  The reaction of various ethyl 3-[[2-(1-hydroxyiminoalkyl)phenyl]carbamoyl]acrylates (2) with electron deficient olefins proceeds via a sequential dipole formation, dipolar cycloaddition sequence to furnish the tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and tetrahydroisoxazolo[4,3-c]quinolin-4(5H) (4) and (6). The product distribution reflects the nature of the reacting olefin and the position and extent of substitution on the acrylate moiety.