3-methoxy-3-(naphthalen-2-yl)propanenitrile | 128104-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methoxy-3-(naphthalen-2-yl)propanenitrile
• 英文别名: 3-Methoxy-3-(2-naphthalenyl)propionitrile；3-methoxy-3-naphthalen-2-ylpropanenitrile
• CAS: 128104-68-7
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: OQEQWDHRRWEMQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-3-(naphthalen-2-yl)propanenitrile 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.5h， 以75%的产率得到N-hydroxy-3-methoxy-3-(2-naphthalenyl)propanimidamide
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006
• 作为产物：
  描述：

  2-萘甲醛 在 正丁基锂 、 sodium hydride 作用下， 反应 2.5h， 生成 3-methoxy-3-(naphthalen-2-yl)propanenitrile
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006

文献信息

• Novel naphthalenyl-3H-1,2,3,5-oxathiadiazole 2-oxides useful as
  申请人：American Home Products Corporation

  公开号：US04895861A1

  公开（公告）日：1990-01-23

  This invention relates to novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides, processes for their preparation, to methods for using the compounds, and to pharmaceutical preparations thereof. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  这项发明涉及新型取代的3H-1,2,3,5-噁硫二唑-2-氧化物，其制备方法，以及使用这些化合物的方法，以及其药物制剂。这些化合物具有药理特性，使它们对于治疗糖尿病及相关疾病有益。
• One-pot silyl ketene imine formation-nucleophilic addition reactions of acetonitrile with acetals and nitrones
  作者：C. Wade Downey、Grace Ann L. Robertson、Jhonmattew Santa、Kari R. Flicker、William M. Stith

  DOI：10.1016/j.tetlet.2019.151537

  日期：2020.2

  promote the conversion of acetonitrile to its silyl ketene imine in situ when acetonitrile is employed as solvent. Residual TMSOTf acts as a Lewis acid catalyst to activate acetals and nitrones in the reaction mixture, yielding β-methoxynitriles and β -(silyloxy)aminonitriles, respectively. Some reaction products undergo elimination under the reaction conditions to provide the α, β -unsaturated nitrile

  当使用乙腈作为溶剂时，三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）和三烷基胺碱可促进乙腈原位转化为其甲硅烷基烯酮亚胺。残留的TMSOTf充当路易斯酸催化剂，以活化反应混合物中的乙缩醛和硝酮，分别生成β-甲氧基腈和β-（甲硅烷氧基）氨基腈。一些反应产物在反应条件下被消除，以直接提供α，β-不饱和腈。
• Mukaiyama addition of (trimethylsilyl)acetonitrile to dimethyl acetals mediated by trimethylsilyl trifluoromethanesulfonate
  作者：C. Wade Downey、Alice Y.-K. Lee、John R. Goodin、Courtney J. Botelho、William M. Stith

  DOI：10.1016/j.tetlet.2017.07.082

  日期：2017.9

  (Trimethylsilyl)acetonitrile reacts smoothly with dimethyl acetals in the presence of stoichiometric trimethylsilyl trifluoromethanesulfonate (TMSOTf) to yield β-methoxynitriles. The ideal substrates for this reaction are acetals derived from aromatic aldehydes. Elimination to the corresponding α,β-unsaturated nitriles is observed as the major product in the case of electron-rich acetals. A mechanistic

  在化学计量的三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）存在下，（三甲基甲硅烷基）乙腈与二甲基乙缩醛平稳反应，生成β-甲氧基腈。该反应的理想底物是衍生自芳族醛的缩醛。在富含电子的乙缩醛的情况下，观察到消除了相应的α，β-不饱和腈是主要产物。提出了一种机械假说，包括甲硅烷基腈异构化为亲核的N-甲硅烷基烯酮亚胺。
• Substituted and unsubstituted naphthalenyl-3H-1,2,3,5-oxthiadiazole 2-oxides
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0393940A1

  公开（公告）日：1990-10-24

  This invention relates to compounds of structural formula (I) and tautomeric forms thereof wherein R¹ and R² are independently hydrogen, lower alkyl containing 1 to 6 carbon atoms, alkoxy containing 1 to 6 carbon atoms, ethynyl, methylthio, nitro, halogen,nitrile, trifluoro-methyl, vinyl or benzyloxy in which the phenyl group is optionally substituted by one or more substituents selected from halogen,lower alkyl containing 1 to 6 carbon atoms and alkoxy containing 1 to 6 carbon atoms; Z is wherein R³ is hydrogen, lower alkyl containing 1 to 3 carbon atoms, alkoxy containing 1 to 2 carbon atoms, or benzyl; R⁴ is lower alkyl containing 1 to 3 carbon atoms, alkoxy containing 1 to 2 carbon atoms, or benzyl; n¹ is 0, 1 or 2; n² is 0, 1 or 2; or Z is -S-CH₂-, -SO₂-CH₂, or -OCH₂-; or Z is -C(R⁵)=C(R⁶)-, wherein R⁵ and R⁶ are independently hydrogen or lower alkyl containing 1 to 3 carbon atoms and their pharmaceutically acceptable salts. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions. The invention also provides processes for their preparation, methods of using the compounds and pharmaceutical compositions containing them.

  本发明涉及结构式 (I) 的化合物及其同分异构体形式 及其同分异构体形式 其中 R¹ 和 R² 独立地为氢、含 1 至 6 个碳原子的低级烷基、含 1 至 6 个碳原子的烷氧基、乙炔基、甲硫基、硝基、卤素、腈、三氟甲基、乙烯基或苄氧基，其中苯基任选被一个或多个选自卤素、含 1 至 6 个碳原子的低级烷基和含 1 至 6 个碳原子的烷氧基的取代基取代；Z 为 其中 R³ 是氢、含 1 至 3 个碳原子的低级烷基、含 1 至 2 个碳原子的烷氧基或苄基； R⁴ 是含 1 至 3 个碳原子的低级烷基、含 1 至 2 个碳原子的烷氧基或苄基； n¹ 是 0、1 或 2；n² 是 0、1 或 2；或 Z 是 -S-CH₂-、-SO₂-CH₂ 或 -OCH₂-；或 Z 是 -C(R⁵)=C(R⁶)-，其中 R⁵ 和 R⁶ 独立地是氢或含有 1 至 3 个碳原子的低级烷基及其药学上可接受的盐。这些化合物具有药物特性，有利于治疗糖尿病及相关疾病。本发明还提供了这些化合物的制备工艺、使用方法以及含有这些化合物的药物组合物。
• US4895861A
  申请人：——

  公开号：US4895861A

  公开（公告）日：1990-01-23