2-(3,4-二甲氧基苯基)-2-(吗啉-1-基)乙腈 | 37673-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3,4-二甲氧基苯基)-2-(吗啉-1-基)乙腈
• 英文名称: 2-(3,4-dimethoxyphenyl)-2-(morpholin-1-yl)acetonitrile
• 英文别名: (3,4-dimethoxy-phenyl)-morpholin-4-yl-acetonitrile；1-(3,4-dimethoxyphenyl)-1-N-morpholinoacetonitrile；(3,4-dimethoxyphenyl)(morpholin-4-yl)acetonitrile；(3,4-dimethoxyphenyl)-morpholin-4-yl-acetonitrile；<3,4-Dimethoxy-phenyl>-morpholino-essigsaeurenitril；2-Morpholino-2-(3,4-dimethoxyphenyl)acetonitrile；2-(3,4-dimethoxyphenyl)-2-morpholin-4-ylacetonitrile
• CAS: 37673-11-3
• 化学式: C₁₄H₁₈N₂O₃
• 分子量: 262.309
• InChiKey: OWTSANYWIHFQRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-(3,4-二甲氧基苯基)-2-(吗啉-1-基)乙腈 在 甲醇 、 sodium tetrahydroborate 、 copper(ll) sulfate pentahydrate 、 水 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 31.0h， 生成 (2R,6S)-2-(3,4-dimethoxyphenyl)-6-(4-methoxyphenethyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  使用酰基阴离子化学合成 (+)-Centrolobine 及其类似物

  摘要：

  开发了一种基于酰基阴离子化学的新路线，用于合成 (+)-centrolobine 及其类似物。酸催化的苄基阳离子引发的环化是顺式立体选择性形成的关键步骤

  DOI：

  10.1002/ejoc.201300097
• 作为产物：
  描述：

  吗啉 、 3,4-二甲氧基苯甲醛 、 丙酮氰醇 在 sulfuric acid supported on silica gel 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以78%的产率得到2-(3,4-二甲氧基苯基)-2-(吗啉-1-基)乙腈
  参考文献：
  名称：

  Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.03.067

文献信息

• The asymmetric synthesis of aryltetralin lignans: (−)-isolariciresinol dimethyl ether and (−)-deoxysikkimotoxin
  作者：Don M. Coltart、James L. Charlton

  DOI：10.1139/v96-011

  日期：1996.1.1

  (−)-deoxysikkimotoxin (7) have been carried out, in an attempt to exploit a synthetic strategy recently developed for the synthesis of (−)-deoxypodophyllotoxin (1, R1 = -CH2−, Ar = 3,4,5-trimethoxyphenyl). In so doing, a generalized method for the synthesis of aryltetralin lignans has been developed that should be applicable to a variety of substitution patterns and stereochemistries. A one-pot, 100%

  已经进行了 (-)-异落叶松树脂醇二甲醚 (6) 和 (-)-deoxysikkimotoxin (7) 的全不对称合成，试图利用最近开发的合成策略来合成 (-)-deoxypodophyllotoxin (1) ，R1 = -CH2-，Ar = 3,4,5-三甲氧基苯基）。在这样做时，已经开发了合成芳基四氢化萘木酚素的通用方法，该方法应该适用于各种取代模式和立体化学。已经开发了一种一锅式 100% 区域选择性还原-内酯化程序，用于将酯 18b 转化为 (-)-脱氧锡基莫毒素，在该步骤中得到 93% 的分离产率。关键词：邻醌二甲烷，木脂素，Diels-Alder，不对称，扁桃酸。
• 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。
• Synthesis of Unsymmetrical Linear Diarylheptanoids and their Enantiomers and Antiproliferative Activity Studies
  作者：Kasireddy Sudarshan、Govindaraj Perumal、Indrapal Singh Aidhen、Mukesh Doble

  DOI：10.1002/ejoc.201801211

  日期：2018.12.6

  A new route for the synthesis of unsymmetrical linear diarylheptanoids 1 and their enantiomers 2 via a common electrophilic intermediate 3 is presented using acyl anion chemistry and Wittig olefination. The cytotoxic activity of all the synthesized linear diarylheptanoids is tested.

  使用酰基阴离子化学和Wittig烯烃化反应，提出了一种通过常见的亲电子中间体3合成不对称线性二芳基庚烷类化合物1及其对映异构体2的新途径。测试所有合成的线性二芳基庚烷的细胞毒活性。
• Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid as a Recyclable Solid Acid Catalyst for the Synthesis of α-Aminonitriles
  作者：Tahere RAHI、Mojtaba BAGHERNEJAD、Khodabakhsh NIKNAM

  DOI：10.1016/s1872-2067(11)60383-5

  日期：2012.7

  Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize α-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction

  二氧化硅键合的 N-丙基二亚乙基三胺氨基磺酸（SBPDSA）被用作可回收的催化剂来合成 α-氨基腈。这些合成包括醛、胺和氰化三甲基甲硅烷在室温温和反应条件下的一锅缩合反应。SBPDSA 在苯甲醛、苯胺和氰化三甲基硅烷的缩合反应中循环使用 7 次，催化活性没有降低。
• Pawar; Waghmare; Lokhande, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 11, p. 2549 - 2551
  作者：Pawar、Waghmare、Lokhande

  DOI：——

  日期：——