2-甲基萘-1-甲腈 | 20944-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-甲基萘-1-甲腈
• 英文名称: 2-methyl-1-naphthonitrile
• 英文别名: 1-cyano-2-methylnaphthalene；2-Methylnaphthalene-1-carbonitrile
• CAS: 20944-85-8
• 化学式: C₁₂H₉N
• mdl: MFCD06496275
• 分子量: 167.21
• InChiKey: MSGUYMCVLYTSNE-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  325.4±11.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-甲基萘-1-甲腈 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 20.0h， 生成 2-benzyl-naphthalene-1-carbonitrile
  参考文献：
  名称：

  Copper-Catalyzed Benzylic C−H Oxygenation under an Oxygen Atmosphere via N-H Imines as an Intramolecular Directing Group

  摘要：

  Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.

  DOI：

  10.1021/ol200425c
• 作为产物：
  描述：

  2-甲基萘 在 N-甲基吡咯烷酮 、 溴 、 碘 、 铁粉 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 2-甲基萘-1-甲腈
  参考文献：
  名称：

  2-和4-（5-芳基戊-4-烯基）-1-氰基萘的分子内光环加成反应

  摘要：

  研究了在萘环的C-2或C-4处含有5-芳基戊-4-烯基的1-氰基萘衍生物的光反应。C-2衍生物在苯或CH 3 CN中的光反应生成分子内[2 + 2]和[3 + 2]光环加合物。带有富电子基团和贫电子苯基基团的物质分别优先产生[2 + 2]和[3 + 2]光环加合物。相反，C-4连接的1-氰基萘的光反应产生的分子内[4 + 2]光环加合物为主要产物，而三环化合物的立体异构体为次要产物。通过使用二苯甲酮或米歇尔酮三重态光敏作用促进[4 + 2]光环加合物的形成，并用O 2淬灭或二茂铁。分子内单线态激基复合物，作为这些反应的机理途径中的重要中间体，支配着2-和4-（5-芳基戊-4-烯基）-1-氰基萘的光反应中的位点选择性。另外，观察到[4 + 2]光环加合物在辐照条件下进行二-π-甲烷重排以产生角三喹烷衍生物。

  DOI：

  10.1016/j.jphotochem.2019.01.033

文献信息

• Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040054173A1

  公开（公告）日：2004-03-18

  Compounds having activity against production of an inflammatory cytokine of formula (I)′: 1 A′ is pyrrole; R 1′ is phenyl or naphthyl; R 2′ is pyridyl or pyrimidinyl; R 3′ is (IIa)′, (IIb)′ or (IIc)′: 2 m′ is 1; E′ is nitrogen; D′ is >C(R 5′ )—, R 5′ is hydrogen, Substituent &agr;′ or Substituent &bgr;′; B′ is nitrogen-containing 5-membered heterocyclic; R 4′ is 1 to 3 substituents from Substituent &agr;′, Substituent &bgr;′ and Substituent &ggr;′; R 1′ and R 3′ are bonded to two atoms of the pyrrole adjacent to the pyrrole atom bonded to R 2′ ; Substituent &agr;′ is hydroxyl, nitro, cyano, halogen, alkoxy, halogeno alkoxy, alkylthio, halogeno alkylthio or —NR a′ R b′ ; R a′ and R b′ are hydrogen, alkyl, alkenyl, alkynyl, aralkyl or alkylsulfonyl, or R a′ and R b′ with the nitrogen atom form a heterocyclyl; Substituent &bgr;′ is alkyl, alkenyl, alkynyl, aralkyl or cycloalkyl; Substituent &ggr;′ is oxo, hydroxyimino, alkoxyimino, alkylene, alkylenedioxy, alkylsulfinyl, alkylsulfonyl, aryl, aryloxy, alkylidenyl or aralkylidenyl.

  具有对抗公式(I)′炎症细胞因子生成活性的化合物： 1 A′是吡咯；R 1′ 是苯基或萘基；R 2′ 是吡啶基或嘧啶基；R 3′ 是(IIa)′，(IIb)′或(IIc)′： 2 m′是1；E′是氮；D′是>C(R 5′ )—, R 5′ 是氢，取代基α′或取代基β′；B′是含氮的5-成员杂环；R 4′ 是来自取代基α′，取代基β′和取代基γ′的1至3个取代基；R 1′ 和R 3′ 分别与吡咯环上与R 2′ 相连的吡咯原子的两个相邻原子成键；取代基α′是羟基，硝基，氰基，卤素，烷氧基，卤代烷氧基，烷基亚砜，卤代烷基亚砜或—NR a′ R b′ ；R a′ 和R b′ 是氢，烷基，烯基，炔基，芳烷基或烷基亚磺酰基，或者R a′ 和R b′ 与氮原子形成杂环；取代基β′是烷基，烯基，炔基，芳烷基或环烷基；取代基γ′是氧代，羟基亚胺，烷氧基亚胺，亚烷基，亚烷基二氧，烷基亚磺酰基，烷基亚磺酰基，芳基，芳氧基，亚烷基或芳亚烷基。
• Facile One-Pot Transformation of Arenes into Aromatic Nitriles under Metal-Cyanide-Free Conditions
  作者：Toshiyuki Tamura、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1002/ejoc.201403672

  日期：2015.3

  Electron-rich arenes bearing methyl or methoxy groups on the aromatic ring were treated with dichloromethyl methyl ether and ZnBr2, and then with molecular iodine and aq. ammonia to give the corresponding aromatic nitriles in good yields. Using this method, febuxostat was efficiently prepared from 4-bromophenol in four steps. The method can be used for the preparation of aromatic nitriles from arenes

  芳环上带有甲基或甲氧基的富电子芳烃用二氯甲基甲基醚和 ZnBr2 处理，然后用分子碘和水溶液处理。氨以良好的收率得到相应的芳香腈。使用这种方法，可以通过四步从 4-溴苯酚有效地制备非布司他。该方法可用于在无金属氰化物条件下由芳烃一锅法制备芳香腈。
• Acetonitrile as a Cyanating Reagent: Cu-Catalyzed Cyanation of Arenes
  作者：Yamin Zhu、Mengdi Zhao、Wenkui Lu、Linyi Li、Zengming Shen

  DOI：10.1021/acs.orglett.5b00886

  日期：2015.6.5

  A novel approach to the Cu-catalyzed cyanation of simple arenes using acetonitrile as an attractive cyano source has been documented. The C–H functionalization of arenes without directing groups involves a sequential iodination/cyanation to give the desired aromatic nitriles in good yields. A highly efficient Cu/TEMPO system for acetonitrile C–CN bond cleavage has been discovered. TEMPO is used as

  已有文献报道使用乙腈作为有吸引力的氰基源，对简单的芳烃进行铜催化的氰化反应的新方法。不带引导基团的芳烃的C–H功能化涉及顺序的碘化/氰化，以高收率得到所需的芳族腈。已经发现了用于乙腈C-CN键裂解的高效Cu / TEMPO系统。TEMPO用作廉价的氧化剂，可使反应在铜中催化。此外，已将TEMPOCH 2 CN 6鉴定为活性氰化剂，并显示出高的形成-CN部分的反应性。
• Iron(II)‐Catalyzed Direct Cyanation of Arenes with Aryl(cyano)iodonium Triflates
  作者：Zhibin Shu、Wenzhi Ji、Xi Wang、Yujing Zhou、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201309791

  日期：2014.2.17

  A direct oxidative cyanation of arenes under FeII catalysis with 3,5‐di(trifluoromethyl)phenyl(cyano)iodonium triflate (DFCT) as the cyanating agent has been developed. The reaction is applicable to wide range of aromatic substrates, including polycyclic structures and heteroaromatic compounds.

  已经开发了在Fe II催化下使用3,5-二（三氟甲基）苯基（氰基）碘化三氟甲磺酸盐（DFCT）作为氰化剂的芳烃直接氧化氰化反应。该反应适用于多种芳族底物，包括多环结构和杂芳族化合物。
• Heteroaryl-substituted pyrrole derivates, their preparation and their therapeutic uses
  申请人：Sankyo Company Limited

  公开号：EP1243589A1

  公开（公告）日：2002-09-25

  Compounds of formula (I): [wherein: A is a pyrrole ring; R1 is an optionally substituted phenyl or naphthyl group; R2 is an optionally substituted pyridyl or pyrimidinyl group; R3 represents a group of the formula -X-R4, wherein X is a single bond or an alkenylene group, and R4 is an optionally substituted nitrogen-containing heterocyclyl group; selected from the group consisting of 8-azabicyclo[3.2.1]octenyl, 9-azabicyclo[3.3.1]nonenyl and quinuclidinenyl groups, PROVIDED THAT said substituents R1 and R3 are bonded to the two atoms of said pyrrole ring which are adjacent to the atom of the pyrrole ring to which said substituent R2 is bonded] have excellent inhibitory activity against the production of inflammatory cytokines.

  化合物的结构式（I）：[其中：A为吡咯环；R1为可选取代的苯或萘基团；R2为可选取代的吡啶或嘧啶基团；R3代表具有下述结构的基团-X-R4，其中X为单键或烯基链，R4为可选取代的含氮杂环基团；所选取自8-氮杂双环[3.2.1]辛烯基、9-氮杂双环[3.3.1]壬烯基和喹啉环基团，前提是所述取代基R1和R3连接到所述吡咯环的两个相邻原子，这两个原子与所述取代基R2连接的吡咯环原子相邻]具有出色的抑制炎症细胞因子产生活性。