1-甲基-2-氧代-1,2-二氢-4-喹啉甲腈 | 56062-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-甲基-2-氧代-1,2-二氢-4-喹啉甲腈
• 英文名称: 1-methyl-4-cyanoquinolone-2
• 英文别名: 4-cyano-1-methyl-2(1H)-quinolone；1-methyl-2-oxo-1,2-dihydroquinoline-4-carbonitrile；1-Methyl-2-oxo-1,2-dihydro-chinolin-4-carbonitril；1-methyl-2-oxoquinoline-4-carbonitrile
• CAS: 56062-93-2
• 化学式: C₁₁H₈N₂O
• mdl: MFCD12197073
• 分子量: 184.197
• InChiKey: TWZZVKCOABHZHX-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  296.8±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-甲基-2-氧代-1,2-二氢-4-喹啉甲腈 生成 1-甲基-2-氧代-1,2-二氢-喹啉-4-羧酸
  参考文献：
  名称：

  BAILEY A. SYDNEY; MORRIS TREVOR; RASHID ZAFAR, J. CHEM. SOC. PERKIN TRANS. , 1975, PART 1, NO 5, 420-424

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methyl-4-cyano-quinolinium iodide 在 水 、 silver(l) oxide 作用下， 生成 1-甲基-2-氧代-1,2-二氢-4-喹啉甲腈
  参考文献：
  名称：

  Kondo; Ikawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1931, vol. 51, p. 702,705; dtsch. Ref. S. 97

  摘要：

  DOI：

文献信息

• A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water
  作者：Pui Yee Yeung、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/anie.201005121

  日期：2010.11.15

  Cool and compatible: Aryl mesylates and tosylates underwent palladium‐catalyzed cyanation under mild, aqueous conditions at 65–80 °C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl,

  凉爽且相容：芳基甲磺酸酯和甲苯磺酸酯在65-80°C的温和水溶液条件下经历了钯催化的氰化反应（请参见方案）。在许多情况下，可以将水用作没有助溶剂的反应介质，并且在转化过程中，各种取代基R（例如酮，醛，酯，游离胺和腈基）保持完整。Cy =环己基，Ms =甲磺酰基，Ts =对甲苯磺酰基。
• BICYCLIC HETEROCYCLIC DERIVATIVES AS BROMODOMAIN INHIBITORS
  申请人：ORION CORPORATION

  公开号：US20160368906A1

  公开（公告）日：2016-12-22

  The present disclosure provides bicyclic heterocyclic derivatives of formula (I), which may be therapeutically useful, more particularly as bromodomain inhibitors; (I), in which R 1 , R 2 , R 3 , R 4 , L 1 , L 2 , Cy 1 , Cy 2 , X, n, and dotted line have the same meaning given in the specification, and pharmaceutically acceptable salts or pharmaceutically acceptable stereoisomers thereof that are useful in the treatment and prevention of diseases or disorders, in particular their use in diseases or disorders associated as bromodomain inhibitors. The present disclosure also provides preparation of compounds and pharmaceutical formulations comprising at least one of bicyclic heterocyclic derivatives of formula (I), together with a pharmaceutically acceptable carrier, diluent, or excipient.

  本公开提供了公式（I）的双环杂环衍生物，可能在治疗上有用，更具体地作为溴结构域抑制剂；（I）中，R1、R2、R3、R4、L1、L2、Cy1、Cy2、X、n和虚线具有规范中给定的相同含义，以及其在治疗和预防疾病或疾病中有用，特别是在与溴结构域抑制剂相关的疾病或疾病中的使用。本公开还提供了制备化合物和包括至少一种公式（I）的双环杂环衍生物的药物配方，以及药学上可接受的载体、稀释剂或赋形剂。
• A copper(II)-mediated radical cross-dehydrogenative coupling/sulfinic acid elimination approach to 2-quinolones
  作者：Ryan M. Gorman、Timothy E. Hurst、Wade F. Petersen、Richard J.K. Taylor

  DOI：10.1016/j.tet.2019.130711

  日期：2019.12

  cyclisation procedure to prepare 4-carboxy-quinolin-2-ones via a one-pot Cu(II)-mediated radical cross-dehydrogenative coupling/sulfinic acid elimination of linear anilides is described. Extensions to more complex substrates are also reported as are applications in target synthesis allowing access to natural products isolated from Oryza sativa and HOFQ.

  描述了一种新的环化程序，可通过一锅Cu（II）介导的自由基，交叉脱氢偶联/亚磺酸消除线性苯胺来制备4-羧基-喹啉-2-酮。还报道了扩展到更复杂的底物，以及在靶标合成中的应用，从而允许获得从稻和HOFQ中分离的天然产物。
• Synthesis of Phenanthridones Using Diels-Alder Reactions of 4-Substituted 2(1H)-Quinolones Acting as Dienophiles.
  作者：Reiko FUJITA、Kazuhiro WATANABE、Toshiteru YOSHISUJI、Hisao MATSUZAKI、Yoshihiro HARIGAYA、Hiroshi HONGO

  DOI：10.1248/cpb.49.407

  日期：——

  Diels-Alder reactions of 2(1H)-quinolones having an electron-withdrawing group at the 4-position with 1,3-butadiene derivatives were carried out to give the phenanthridones richly functionalized under the conditions of atmospheric and high pressure. Furthermore, the reactivities of 4-substituted 2(1H)-quinolones acting as a dienophile were examined using MO calculation.

  进行了在4-位具有吸电子基团的2（1H）-喹诺酮与1,3-丁二烯衍生物的Diels-Alder反应，得​​到了在大气压和高压条件下功能化的菲啶酮。此外，使用MO计算检查了作为亲二烯体的4-取代的2（1H）-喹诺酮的反应性。
• Diels-Alder Reaction of 1,3-Butadiene Derivatives with 1-Methyl-2(1H)-quinolones Having an Electron-Withdrawing Group at the 4-Position.
  作者：Reiko FUJITA、Kazuhiro WATANABE、Toshiteru YOSHISUJI、Hiroshi HONGO、Hisao MATSUZAKI

  DOI：10.1248/cpb.49.900

  日期：——

  Diels-Alder reactions of 1-methyl-2(1H)-quinolones having an electron-withdrawing group at the 4-position with isoprene, butadiene sulfone, and cyclohexadiene were performed to yield functionalized phenanthridones stereoselectively at atmospheric and at high pressure. Regioselectivity and stereochemistry of a methoxycarbonyl group were studied using the semi-empirical and ab initio MO methods, respectively

  进行了在4-位具有吸电子基团的1-甲基-2（1H）-喹诺酮与异戊二烯，丁二烯砜和环己二烯的狄尔斯-阿尔德反应，在大气压和高压下立体选择性地生成官能化的菲啶酮。分别使用半经验和从头算MO方法研究了甲氧基羰基的区域选择性和立体化学。