2-(Benzo<1,2-d><1,3>dioxol-5-yl)-2-morpholinoacetonitril | 37673-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(Benzo<1,2-d><1,3>dioxol-5-yl)-2-morpholinoacetonitril
• 英文别名: α-(3,4-methylenedioxyphenyl)-α-morpholinoacetonitrile；α-3,4-(methylenedioxy)phenyl-α-(4-morpholino)acetonitrile；2-(3,4-dioxymethylenphenyl)-2-(morpholin-1-yl)acetonitrile；3,4-Methylendioxyphenyl-4-morpholinacetonitril；benzo[1,3]dioxol-5-yl-morpholin-4-yl-acetonitrile；Piperonyl-morpholinyl-essigsaeure-nitril；2-(2H-1,3-benzodioxol-5-yl)-2-(morpholin-4-yl)acetonitrile；2-(1,3-benzodioxol-5-yl)-2-morpholin-4-ylacetonitrile
• CAS: 37673-10-2
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: JUDGQLZUYWJUAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(Benzo<1,2-d><1,3>dioxol-5-yl)-2-morpholinoacetonitril 在 sodium hydride 、 copper(II) sulfate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 1-苯并[1,3]二氧代-5-丁烷-1,3-二酮
  参考文献：
  名称：

  Propargyl Bromide as an Excellent α-Bromoacetone Equivalent:  Convenient and New Route to α-Aroylacetones

  摘要：

  A variety of alpha-aroylacetones 4a-g have been prepared in excellent yields following a new protocol wherein alpha-aminonitriles la-g as the aryl acyl anion equivalents readily react with propargyl bromide as the alpha-bromoacetone equivalent. The alkylated product undergoes one-pot unmasking of the keto functionality along with Markovnikov's hydration of the terminal alkyne with CuSO(4)center dot 5H(2)O in aqueous methanol at 60 degrees C to furnish the desired target in excellent isolated yields.

  DOI：

  10.1021/jo051538w
• 作为产物：
  描述：

  [2-(1,3-benzodioxol-5-yl)-2-morpholin-4-ylethenylidene]azanide 生成 2-(Benzo<1,2-d><1,3>dioxol-5-yl)-2-morpholinoacetonitril
  参考文献：
  名称：

  BORDWELL, F. G.;BAUSCH, MARK J.;CHENG, JIN-PEI;CRIPE, THONAS H.;LYNCH, TS+, J. ORG. CHEM., 55,(1990) N, C. 58-63

  摘要：

  DOI：

文献信息

• Synthesis of 3-Arylisocoumarins by Using Acyl Anion Chemistry and Synthesis of Thunberginol A and Cajanolactone A
  作者：Kasireddy Sudarshan、Manash Kumar Manna、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.201403524

  日期：2015.3

  new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C–C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural

  3-芳基异香豆素和8-羟基-3-芳基异香豆素的合成新策略通过使用酰基阴离子化学进行初始C-C键形成研究。得到的酮酯和酮内酯作为中间体进行基于促进的分子内环化，以良好的产率得到3-芳基异香豆素。所开发的方法用于合成重要的天然产物 thunberginol A 和 cajanolactone A。
• Derivate des 1.3-Benzdioxols, 53 [1] Darstellung von N-Alkyl-2-aryl-pyrrolidinen
  作者：Franz Dallacker、Walter Jouck

  DOI：10.1515/znb-1984-1122

  日期：1984.11.1

  The conversion of the metal organyls of 1,3-benzdioxole, pyrido[2.3-d]-1.3-dioxole and pyrido[2.3-b]-1.4-dioxene using lactimethers did not prove successful. The N-alkyl-2-aryl-pyrrolidines 10a-c, 11a-c, 12a, 13a and 14a were synthesized from the aldehydes 4a-c via the γ-ketonitriles 7a-c and the 2-aryl-⊿¹-pyrrolidines 8 a-c; in some cases, the recovery was high.

  摘要：使用内酯醚对1,3-苯并二氧杂环己烷基金属有机物、吡啶并[2.3-d]-1.3-二氧杂环己烷基金属有机物和吡啶并[2.3-b]-1.4-二氧杂环己烯基金属有机物进行转化并不成功。N-烷基-2-芳基吡咯烷10a-c、11a-c、12a、13a和14a通过醛4a-c经γ-酮腈7a-c和2-芳基-⊿1-吡咯烷8a-c合成；在某些情况下，收率很高。
• Aidhen, Indrapal Singh; Narasimhan, N. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 2, p. 211 - 221
  作者：Aidhen, Indrapal Singh、Narasimhan, N. S.

  DOI：——

  日期：——
• Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever
  作者：Aurora L. Carreño Otero、Leonor Y. Vargas Méndez、Jonny E. Duque L.、Vladimir V. Kouznetsov

  DOI：10.1016/j.ejmech.2014.03.067

  日期：2014.5

  Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like alpha-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained alpha-aminonitriles could be considered as AChEIs with micromolar IC50 values ranging from 42.0 to 478.0 mu M (10.3-124.0 mu g/mL). Among this series, the best AChE inhibitor was the Pyrrolidine alpha-aminonitrile 3 (IC50 = 42 mu M) followed by the piperidine alpha-aminonitriles 2 and 6 (IC50 = 45 mu M and IC50 = 51 mu M, respectively), and the compound 7 (IC50 = 51 mu M). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Alkylations and acylations of .alpha.-(aryl)-4-morpholineacetonitriles (masked acyl anion equivalents) and their use in 1,4-additions
  作者：Francis J. McEvoy、J. Donald Albright

  DOI：10.1021/jo00393a030

  日期：1979.12

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