3-(1-acetyl-3-methylindolin-3-yl)propanenitrile | 1421358-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(1-acetyl-3-methylindolin-3-yl)propanenitrile
• 英文别名: 3-(1-acetyl-3-methyl-2H-indol-3-yl)propanenitrile
• CAS: 1421358-30-6
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: TWJLCISFNBXGIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙酰苯胺 在 吡啶 、 二(叔丁基羰基氧基)碘苯 、 palladium diacetate 、 silver fluoride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.33h， 生成 3-(1-acetyl-3-methylindolin-3-yl)propanenitrile
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Arylalkylation of Unactivated Alkenes: Dual C–H Bond Cleavage of Anilines and Acetonitrile

  摘要：

  A palladium-catalyzed oxidative arylalkylation of unactivated alkenes involving dual C-H bond cleavage of arene and acetonitrile was developed. This reaction was promoted by pyridine as a ligand, and the ratio of palladium to pyridine is vital for this transformation. A series of nitrile-containing indolines were efficiently provided in moderate to good yields.

  DOI：

  10.1055/s-0032-1316555

文献信息

• Synthesis of cyanoalkyl indolines through cyanoalkylarylation of N-allyl anilines with alkyl nitriles under metal-free and neutral conditions
  作者：Deqiang Liang、Xuemei Song、Lichun Xu、Yitong Sun、Ying Dong、Baoling Wang、Weili Li

  DOI：10.1016/j.tet.2019.05.018

  日期：2019.6

  An α-C(sp3)−H functionalization of alkyl nitriles under metal-free and neutral conditions is presented. In the presence of di-tert-butyl peroxide (DTBP), N-allyl anilines underwent exo-selective cyanoalkylation/cyclization cascade, providing a direct access to 3-cyanoalkyl indolines. Previously, a transition-metal catalyst and/or a strong base were generally required to activate nitrilic α-C−H bonds

  提出了在无金属和中性条件下烷基腈的α-C（sp 3）-H官能化。在二-的存在下叔丁基过氧化物（DTBP），ñ -烯丙基苯胺后行外型-选择性氰烷基化/环化级联，提供到3-氰基二氢吲哚的直接访问。以前，通常需要过渡金属催化剂和/或强碱来激活腈基α-CH键。该反应具有广泛的底物范围和低成本，并且伯，仲和叔吲哚-3-基腈都可以组装。
• Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds
  作者：Guanglong Pan、Qian Yang、Wentao Wang、Yurong Tang、Yunfei Cai

  DOI：10.3762/bjoc.17.89

  日期：——

  photocatalytic cyanomethylarylation of alkenes with acetonitrile has been established using K-modified carbon nitride (CN-K) as a recyclable semiconductor photocatalyst. This protocol, employing readily accessible alkyl N-hydroxyphthalimide (NHPI) ester as a radical initiator, allows the efficient construction of a broad array of structural diverse nitrogenous heterocyclic compounds including indolines, oxindoles

  使用 K 改性氮化碳（CN-K）作为可回收半导体光催化剂，建立了可见光介导的烯烃与乙腈的异相光催化氰甲基芳基化反应。该方案采用易于获得的烷基N-羟基邻苯二甲酰亚胺 (NHPI) 酯作为自由基引发剂，可以有效构建多种结构多样的含氮杂环化合物，包括二氢吲哚、羟吲哚、异喹啉酮和异喹啉二酮。
• N-烯丙基苯胺氰烷基化合成氰烷基吲哚啉的方法
  申请人：昆明学院

  公开号：CN109824573B

  公开（公告）日：2022-05-10

  本发明提供一种N‑烯丙基苯胺氰烷基化合成氰烷基吲哚啉的方法，使用廉价烷基腈与特定非活化烯烃在DTBP作用，在无金属和中性条件下，N‑烯丙基苯胺类化合物发生exo选择性的氰烷基化/环化级联反应，生成3‑氰烷基吲哚啉。本发明方法反应无需金属和强碱、底物范围广，即使是化合物中存在磺酰基保护基时反应也能顺利发生；而且使用本发明方法，一级、二级和三级腈产物都可以顺利合成，同时反应条件温和、操作简单，适合工业化推广。
• Cascade arylalkylation of unactivated alkenes for the construction of cyanomethyl-substituted dihydroisoquinolinones and indolines
  作者：Changduo Pan、Yun Wang、Chao Wu、Jin-Tao Yu

  DOI：10.1016/j.catcom.2019.105802

  日期：2019.11

  ation of N-allylbenzamide with acetonitrile to form dihydroisoquinolinones was described. The direct functionalizations of the sp3 CH bond of acetonitrile and the sp2 CH bond of the phenyl ring were involved in this reaction. Cascade arylalkylation of N-allylanilines was also achieved under the same conditions to provide cyanomethylated indolines in good yields.

  描述了N-烯丙基酰胺与乙腈的自由基氰基甲基化/芳基化以形成二氢异喹啉酮。SP的直接官能化3 Ç乙腈的H键和SP 2 Ç苯基环的H键参与了该反应。在相同条件下，还可以实现N-烯丙啉的级联芳烷基化，从而以高收率提供氰基甲基化的二氢吲哚。
• Palladium-Catalyzed Oxidative Arylalkylation of Unactivated Alkenes: Dual C–H Bond Cleavage of Anilines and Acetonitrile
  作者：Guosheng Liu、Hao Zhang、Pinhong Chen

  DOI：10.1055/s-0032-1316555

  日期：——

  A palladium-catalyzed oxidative arylalkylation of unactivated alkenes involving dual C-H bond cleavage of arene and acetonitrile was developed. This reaction was promoted by pyridine as a ligand, and the ratio of palladium to pyridine is vital for this transformation. A series of nitrile-containing indolines were efficiently provided in moderate to good yields.