2-(5-methylpyridin-2-yl)benzonitrile | 155617-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(5-methylpyridin-2-yl)benzonitrile
• 英文别名: 2-(5-Methyl-2-pyridyl)benzonitrile
• CAS: 155617-73-5
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: FXRJRJPWWNQURG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-methylpyridin-2-yl)benzonitrile 在 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， 以67%的产率得到2-[5-(bromomethyl)pyridin-2-yl]benzonitrile
  参考文献：
  名称：

  Fused heterocyclic compounds, having angiotensin II antagonistic activity

  摘要：

  公式(I)的融合杂环化合物：##STR1## 其中R.sup.1是一个可选地取代的烃基团，可以通过一个杂原子连接；R.sup.2是一个能够形成阴离子或可转换成阴离子的团；R.sup.3是一个包含至少一个杂原子的可选地取代的芳香烃或杂环基团；X是R.sup.3基团和环W基团之间的直接键或原子长度为两个或更少的间隔物；W是一个包含至少一个杂原子的可选地取代的芳香烃或杂环基团；a、c和d独立地选自一个或两个可选地取代的碳原子和一个或两个可选地取代的杂原子的组；b和e独立地选自一个可选地取代的碳原子和一个可选地取代的氮原子的组，其中b或e之一必须是氮；虚线是一个形成一双键的键；n是一个1或2的整数，并且当a，即一个可选地取代的碳原子，与R.sup.1一起时，以下组：##STR2## 可以形成一个环状结构；当##STR3## 是一个苯并咪唑、噻吩[3,4-d]咪唑或噻吩[2,3-d]咪唑环时，至少一个是##STR4## 和R.sup.3的可选地取代的杂环基团；以及它们的药用可接受盐，具有强大的血管紧张素II拮抗活性和抗高血压活性，因此作为治疗循环系统疾病如高血压病、心脏病（例如心肌炎、心力衰竭、心肌梗死等）、中风、脑梗塞、肾炎等的治疗剂是有用的。

  公开号：

  US05389641A1
• 作为产物：
  描述：

  5-甲基-2-苯基吡啶 、 偶氮二异丁腈 在 氧气 、 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以71%的产率得到2-(5-methylpyridin-2-yl)benzonitrile
  参考文献：
  名称：

  Copper-Mediated Direct Aryl C–H Cyanation with Azobisisobutyronitrile via a Free-Radical Pathway

  摘要：

  An unprecedented protocol for the copper-mediated direct cyanation of aryl C-H by employing 2,2'-azobisisobutyronitrwile (AIBN) as a free radical "CN" source is presented. The protocol not only provides a more efficient pathway for the synthesis of aryl nitriles in terms of the yields and the loading amount of copper salts but also, more importantly, represents a novel strategy for aryl C-H cyanation via a CN free-radical mechanism as compared to the CN anion-participating protocols often reported.

  DOI：

  10.1021/ol401404y

文献信息

• Copper-mediated C–H cyanation of (hetero)arenes with ethyl (ethoxymethylene)cyanoacetate as a cyanating agent
  作者：Chaorong Qi、Xiaohan Hu、Huanfeng Jiang

  DOI：10.1039/c7cc03384b

  日期：——

  A copper-mediated direct C–H cyanation reaction of (hetero)arenes with ethyl (ethoxymethylene)cyanoacetate as a safe cyanating agent has been developed.

  一种以铜为媒介的直接C-H氰化反应已经开发出来，使用乙基（乙氧亚甲基）氰乙酸乙酯作为安全的氰化试剂，可用于(hetero)芳烃的氰化。
• Copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate
  作者：Jisong Jin、Qiaodong Wen、Ping Lu、Yanguang Wang

  DOI：10.1039/c2cc35046g

  日期：——

  The copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate furnishes aromatic nitriles in moderate to good yields. The cascade process involves a copper-catalyzed aerobic C-H oxidation, a retro-cyanohydrination, and a copper-catalyzed aerobic oxidative C-H functionalization.

  使用苄基腈作为氰化物阴离子替代物进行的铜催化的芳烃氰化，可提供中等至良好收率的芳族腈。级联过程涉及铜催化的好氧CH氧化，逆向氰化和铜催化的好氧氧化CH官能化。
• Cobalt-Catalyzed C–H Cyanation of (Hetero)arenes and 6-Arylpurines with <i>N</i>-Cyanosuccinimide as a New Cyanating Agent
  作者：Amit B. Pawar、Sukbok Chang

  DOI：10.1021/ol503680d

  日期：2015.2.6

  A cobalt-catalyzed C–H cyanation reaction of arenes has been developed using N-cyanosuccinimide as a new electrophilic cyanating agent. The reaction proceeds with high selectivity to afford monocyanated products with excellent functional group tolerance. Substrate scope was found to be broad enough to include a wide range of heterocycles including 6-arylpurines.

  使用N-氰基琥珀酰亚胺作为新型的亲电子氰化剂，已开发出钴催化芳烃的CH氰化反应。反应以高选择性进行，得到具有优异的官能团耐受性的单氰酸酯化产物。发现底物的范围足够宽，可以包括包括6-芳基嘌呤在内的各种杂环。
• Rhodium(<scp>iii</scp>)-catalyzed aromatic C–H cyanation with dimethylmalononitrile as a cyanating agent
  作者：He Li、Sheng Zhang、Xiaoqiang Yu、Xiujuan Feng、Yoshinori Yamamoto、Ming Bao

  DOI：10.1039/c8cc08930b

  日期：——

  A rhodium-catalyzed aromatic C–H bond direct cyanation with safe, bench-stable, and commercially available dimethylmalononitrile as the cyanating agent has been successfully developed by using copper oxide as a promotor. Pyridine, quinoline, pyrimidine and pyrazole were used as the directing group in this type of C–H bond direct cyanation reaction.

  通过使用氧化铜作为促进剂，成功开发出了铑催化的芳香族CH键直接氰化，安全，稳定和可商购的二甲基丙二腈作为氰化剂。吡啶，喹啉，嘧啶和吡唑被用作这种C–H键直接氰化反应的导向基团。
• Fused heterocyclic compounds, their production and use as angiotensin II antagonists
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1327631A2

  公开（公告）日：2003-07-16

  Fused heterocyclic compounds of the formula (I): wherein R1 is an optionally substituted hydrocarbon residue which may be attached through a hetero atom; R2 is a group capable of forming an anion or a group convertible thereinto; R3 is an optionally substituted aromatic hydrocarbon or heterocyclic residue which contains at least one hetero atom; X is a direct bond or a spacer having an atomic length of two or less between the R3 group and the ring W group; W is an optionally substituted aromatic hydrocarbon or heterocyclic residue which contains at least one hetero atom; a,c and d are independently selected from the group consisting of one or two optionally substituted carbon atoms and one or two optionally substituted hetero atoms; b and e are independently selected from the group consisting of one optionally substituted carbon atom and one optionally substituted nitrogen atom; the dotted line is a bond to form one double bond; n is an integer of 1 or 2 and when a, which is an optionally substituted carbon atom, is taken together with R1, the following group: may form a ring group; provided that when is a benzimidazole, thieno[3,4-d]imidazole, or thieno[2,3-d]imidazole ring, at least one of the group: and R3 is an optionally substituted heterocyclic residue ; and the pharmaceutically acceptable salts thereof, have potent angiotensin II antagonistic activity and antihypertensive activity, thus being useful as therapeutic agents for treating circulatory system diseases such as hypertensive diseases, heart diseases (e.g. hypercardia, heart failure, cardiac infarction, etc.), strokes, cerebral apoplexy, nephritis, etc.

  式(I)的融合杂环化合物： 其中 R1 是可通过杂原子连接的任选取代的烃残基；R2 是可形成阴离子的基团或可转化为阴离子的基团；R3 是至少含有一个杂原子的任选取代的芳香烃或杂环残基；X 是 R3 基团与环 W 基团之间的直接键或原子长度为两个或更短的间隔键；W 是至少含有一个杂原子的任选取代的芳香烃或杂环残基； a、c 和 d 独立地选自由一个或两个任选取代的碳原子和一个或两个任选取代的杂原子组成的组；b 和 e 独立地选自由一个任选取代的碳原子和一个任选取代的氮原子组成的组；虚线是形成一个双键的键；n 是 1 或 2 的整数，当作为任选取代的碳原子的 a 与 R1 合在一起时，以下基团 可形成一个环状基团；但当 是苯并咪唑、噻吩并[3,4-d]咪唑或噻吩并[2,3-d]咪唑环时，至少有一个基团： 和 R3 是任选取代的杂环残基；其药学上可接受的盐类具有强效的血管紧张素 II 拮抗活性和降压活性，因此可作为治疗剂用于治疗循环系统疾病，如高血压疾病、心脏病（如心动过速、心力衰竭、心肌梗塞等）、中风、脑中风、肾炎等。