ethyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate | 40674-15-5

• 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: ethyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate
• 英文别名: ethyl 2-(phthalimidooxy)propionate；2-phthalimidooxy-propionic acid ethyl ester；2-(Phthalimido-oxy)-propionsaeureethylester；2-Phthalyliminoxy-propionsaeure-ethylester；ethyl 2-(1,3-dioxoisoindol-2-yl)oxypropanoate
• CAS: 40674-15-5
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: KBBDZJBCADSKJB-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C(Solv: ligroine (8032-32-4))
• 沸点：
  382.8±44.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，惰性气体

反应信息

• 作为反应物：
  描述：

  ethyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate 在 盐酸 、 一水合肼 作用下， 生成 2-aminooxy-propionic acid ethyl ester
  参考文献：
  名称：

  苯并恶唑烷酮的重氮化

  摘要：

  苯并xamsäure和苯苯基取代类似物的类似物-α-Halogencarbonsäureestern苯并xamsäureester（表1中的IV）。Diese reagierten mit Diazomethanstereospezifisch zu den entsprechenden syn - Methyl-benzhydroximsäureestern （表1中的V）。Die Zuordnung der Stereochemie Basilert auf dem Aufbau von XIV和XVIII aus den beiden3-O-Methyl-benzhydroxamsäurenXII和XIII，Dere Stereochemie gesichert ist。

  DOI：

  10.1002/hlca.19690520303
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 丙酸乙酯 在 二叔丁基过氧化物 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以47%的产率得到ethyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate
  参考文献：
  名称：

  羰基化合物与N-羟基酰亚胺的无金属交叉脱氢CO偶联：高反应性自由基在高温下的意外选择行为。

  摘要：

  N-羟基酰亚胺与酮，酯和羧酸的交叉脱氢CO偶联是通过使用二叔丁基过氧化物作为自由基源和脱氢剂来实现的。所提出的方法在实验上很简单，并且证明了对于具有挑战性的CH底物（例如未活化的酯和羧酸）具有出色的效率。结果表明，N-羟基邻苯二甲酰亚胺通过拦截t-BuO•自由基而形成邻苯二甲酰亚胺-N-氧基自由基，从而极大地影响t-BuOOt-Bu的氧化性能。通过选择性自由基交叉重组选择性形成CO偶联产物。

  DOI：

  10.1021/acs.joc.9b02656

文献信息

• Effect of Optically Active Ethyl 2-Phthalimidooxypropionate on the Growth of Cress,<i>Lepidium sativum</i>
  作者：Yukinori TAKEKIDA、Momotoshi OKAZAKI、Yoshihiro SHUTO

  DOI：10.1271/bbb.63.1831

  日期：1999.1

  The effects of 2-phthalimidooxyalkanoic acid derivatives on the germination and root-growth of cress were examined. Since 2-phthalimidooxypropionates were most effective, the optically active ethyl esters were prepared. As the result of biological testing, the (S)-(-)-isomer exhibited stronger activity than the (R)-(+)-isomer. This result is contrary to those from commercial herbicides with similar structures, phenoxy- and oxyphenoxy-propionate-type compounds, where the (R)-isomers are generally known to be the active principles.

  研究了2-邻苯二甲酰亚胺氧基烷酸衍生物对水芹萌发和根生长的影响。由于2-邻苯二甲酰亚胺氧基丙酸酯最为有效，因此制备了光学活性的乙酯。生物测试结果显示，(S)-(-)-异构体比(R)-(+)-异构体表现出更强的活性。这一结果与结构类似、属于苯氧基和羟苯氧基丙酸酯类商业除草剂的情况相反，后者通常认为(R)-异构体是活性成分。
• Alkylation of Allyl/Alkenyl Sulfones by Deoxygenation of Alkoxyl Radicals
  作者：Jia-Bin Han、Ao Guo、Xiang-Ying Tang

  DOI：10.1002/chem.201806138

  日期：2019.2.26

  challenging deoxygenation of alkoxyl radicals from readily accessible alcohol derivatives was developed, affording facile synthesis of functionalized alkenes with good functional group tolerance under mild reaction conditions. Because alkoxyl radicals can easily undergo β‐fragmentations or hydrogen abstractions, this new strategy for deoxygenation of alkoxyl radicals is highly valuable. Moreover, mechanistic

  从容易获得的醇衍生物开发了具有挑战性的烷氧基自由基脱氧剂，可在温和的反应条件下轻松合成具有良好官能团耐受性的官能化烯烃。由于烷氧基自由基很容易发生β片段分解或夺氢现象，因此这种使烷氧基自由基脱氧的新策略非常有价值。此外，机理研究表明，电子中性膦可作为脱氧剂。
• 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.
• 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：——
• Metal-Free Cross-Dehydrogenative C–O Coupling of Carbonyl Compounds with <i>N</i>-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperature
  作者：Igor B. Krylov、Elena R. Lopat’eva、Alexander S. Budnikov、Gennady I. Nikishin、Alexander O. Terent’ev

  DOI：10.1021/acs.joc.9b02656

  日期：2020.2.21

  N-hydroxyphthalimide drastically affects the oxidative properties of t-BuOOt-Bu by intercepting the t-BuO• radicals with the formation of phthalimide-N-oxyl radicals, a species responsible for both hydrogen atom abstraction from the CH reagent and the selective formation of the C-O coupling product by selective radical cross-recombination. The practical applicability of the developed method was exemplified by the

  N-羟基酰亚胺与酮，酯和羧酸的交叉脱氢CO偶联是通过使用二叔丁基过氧化物作为自由基源和脱氢剂来实现的。所提出的方法在实验上很简单，并且证明了对于具有挑战性的CH底物（例如未活化的酯和羧酸）具有出色的效率。结果表明，N-羟基邻苯二甲酰亚胺通过拦截t-BuO•自由基而形成邻苯二甲酰亚胺-N-氧基自由基，从而极大地影响t-BuOOt-Bu的氧化性能。通过选择性自由基交叉重组选择性形成CO偶联产物。