methyl 2-(phthalimidooxy)acrylate | 131042-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: methyl 2-(phthalimidooxy)acrylate
• 英文别名: Methyl 2-[(1,3-dioxoisoindol-2-yl)oxymethyl]prop-2-enoate
• CAS: 131042-53-0
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: SPJGSZCABKLHJR-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  398.1±52.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 methyl 2-(phthalimidooxy)acrylate 在 溶剂黄146 、 一水合肼 作用下， 以 乙醚 、 甲苯 、 甲醇 为溶剂， 反应 6.0h， 生成 Methyl 1-(aminooxymethyl)cyclopropane-1-carboxylate 、 氨基邻苯二甲胺
  参考文献：
  名称：

  1-氨基氧甲基环丙烷羧酸作为βN–O圈和螺旋的组成部分：在溶液和固态下的合成和构象分析

  摘要：

  合成并构象了环丙烷侧链β2，2-氨基氧寡肽。通过1 H NMR，2D NOESY和FT-IR以及X射线晶体学研究对溶液中的βN–O转变和固态βN –O螺旋进行了表征。与二甲基取代的α相比，在α碳键角处的扰动几乎没有观察到变化。这项研究为以更精细的方式设计生物活性拟肽提供了机会。

  DOI：

  10.1016/j.tet.2010.10.037
• 作为产物：
  描述：

  2-(溴甲基)丙烯酸甲酯 、 sodium N-hydroxyphthalimide 以 水 、 丙酮 为溶剂， 反应 16.0h， 以72%的产率得到methyl 2-(phthalimidooxy)acrylate
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of imidooxy derivatives

  摘要：

  Previous results of anticonvulsant activity in several imidooxy carboxylates related to (aminooxy)acetic acid in young chicks, prompted an in-depth reinvestigation of these analogues in mice. A series of 22 succinimidooxy, phthalimidooxy, and naphthalimidooxy carboxylates were synthesized and evaluated for anticonvulsant activity by the National Institute of Neurological and Communicative Disorders and Stroke (NINCDS). Methyl (succinimidooxy)acetate (2d), ethyl (succinimidooxy)acetate (2e), methyl (phthalimidooxy)acetate (3d), ethyl (phthalimidooxy)acetate (3e), and ethyl 2-(phthalimidooxy)propionate (3g), which were initially found to be active as anticonvulsants in young chicks were uniformly inactive in the Phase I seizure tests involving maximal electroshock (MES), pentylenetetrazol (scMet), or neurologic toxicity toxicity (Tox). Several newer analogues, ethyl (succinimidooxy)formate (2c) and methyl 3-(phthalimidooxy)-2-methylacrylate (4h) were found to be active in the scMet (3a) or both (4h) evaluations. Most interesting was the anticonvulsant results of N-(benzyloxy)-2-azaspiro[4.4]nonane-1,3-dione (5b), which displayed anti-MES activity and a protective index (TD50/ED50) of > 4.5.

  DOI：

  10.1021/jm00105a059

文献信息

• EDAFIOGHO, IVAN O.;SCOTT, K. R.;MOORE, JACQUELINE A.;FARRAR, VIDA A.;NICH+, J. MED. CHEM., 34,(1991) N, C. 387-392
  作者：EDAFIOGHO, IVAN O.、SCOTT, K. R.、MOORE, JACQUELINE A.、FARRAR, VIDA A.、NICH+

  DOI：——

  日期：——
• Synthesis and anticonvulsant activity of imidooxy derivatives
  作者：Ivan O. Edafiogho、K. R. Scott、Jacqueline A. Moore、Vida A. Farrar、Jesse M. Nicholson

  DOI：10.1021/jm00105a059

  日期：1991.1

  Previous results of anticonvulsant activity in several imidooxy carboxylates related to (aminooxy)acetic acid in young chicks, prompted an in-depth reinvestigation of these analogues in mice. A series of 22 succinimidooxy, phthalimidooxy, and naphthalimidooxy carboxylates were synthesized and evaluated for anticonvulsant activity by the National Institute of Neurological and Communicative Disorders and Stroke (NINCDS). Methyl (succinimidooxy)acetate (2d), ethyl (succinimidooxy)acetate (2e), methyl (phthalimidooxy)acetate (3d), ethyl (phthalimidooxy)acetate (3e), and ethyl 2-(phthalimidooxy)propionate (3g), which were initially found to be active as anticonvulsants in young chicks were uniformly inactive in the Phase I seizure tests involving maximal electroshock (MES), pentylenetetrazol (scMet), or neurologic toxicity toxicity (Tox). Several newer analogues, ethyl (succinimidooxy)formate (2c) and methyl 3-(phthalimidooxy)-2-methylacrylate (4h) were found to be active in the scMet (3a) or both (4h) evaluations. Most interesting was the anticonvulsant results of N-(benzyloxy)-2-azaspiro[4.4]nonane-1,3-dione (5b), which displayed anti-MES activity and a protective index (TD50/ED50) of > 4.5.
• 1-Aminoxymethylcyclopropanecarboxylic acid as building block of β N–O turn and helix: synthesis and conformational analysis in solution and in the solid state
  作者：Xiao-Wei Chang、Qing-Chuan Han、Zhi-Gang Jiao、Lin-Hong Weng、Dan-Wei Zhang

  DOI：10.1016/j.tet.2010.10.037

  日期：2010.12

  Cyclopropane side-chained β2,2-aminoxy oligopeptides were synthesized and conformationally studied. β N–O turn in solution and β N–O helix in the solid state was characterized by 1H NMR, 2D NOESY and FT-IR as well as X-ray crystallography studies. Almost no changes has been observed with the disturbance at α carbon bond angle compared with dimethyl substituted one. This study provided the opportunity

  合成并构象了环丙烷侧链β2，2-氨基氧寡肽。通过1 H NMR，2D NOESY和FT-IR以及X射线晶体学研究对溶液中的βN–O转变和固态βN –O螺旋进行了表征。与二甲基取代的α相比，在α碳键角处的扰动几乎没有观察到变化。这项研究为以更精细的方式设计生物活性拟肽提供了机会。