3-(1-acetyl-5-bromo-3-methylindolin-3-yl)propanenitrile | 1421358-37-3

• 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-5-bromo-3-methylindolin-3-yl)propanenitrile
• 英文别名: 3-(3-methyl-1-acetyl-5-bromoindole-3-yl)propanenitrile
• CAS: 1421358-37-3
• 化学式: C₁₄H₁₅BrN₂O
• 分子量: 307.19
• InChiKey: XSYCIFGMINRVTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-溴苯胺 在 吡啶 、 二(叔丁基羰基氧基)碘苯 、 palladium diacetate 、 silver fluoride 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.33h， 生成 3-(1-acetyl-5-bromo-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。