morpholino(quinolin-2-yl)methanone | 78224-46-1

• 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
• 英文名称: morpholino(quinolin-2-yl)methanone
• 英文别名: 2-(Morpholin-4-ylcarbonyl)quinoline；Morpholin-4-yl(quinolin-2-yl)methanone
• CAS: 78224-46-1
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: UFSHEHQPBZNEBK-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  451.1±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  喹哪啶酸 在 4-二甲氨基吡啶 、 palladium diacetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 氯苯 为溶剂， 反应 24.0h， 生成 morpholino(quinolin-2-yl)methanone
  参考文献：
  名称：

  使用叔胺作为氨基供体通过C–O和C–N键活化进行芳基酯的氨解

  摘要：

  已开发出各种芳基酯与惰性叔胺之间通过C-O和C-N键激活进行的氨解反应，可在中性和温和条件下选择性合成各种叔酰胺。该机理可能经历了两个关键步骤：在母体酯中氧化加成酰基C–O键和通过亚胺基型中间体裂解叔胺的C–N键。

  DOI：

  10.1021/jo4023974

文献信息

• Aerobic oxidation of secondary benzylic alcohols and direct oxidative amidation of aryl aldehydes promoted by sodium hydride
  作者：Xinbo Wang、David Zhigang Wang

  DOI：10.1016/j.tet.2011.03.052

  日期：2011.5

  possible mechanistic implications of a simplest oxidant (NaH/air) uncovered on a broad range of useful transformations, including aerobic alcohol oxidations, allylic alcohol isomerizations and oxidations, cyclopropyl alcohol fragmentations, and direct aryl aldehyde oxidative amidations. These readily implementable transition-metal-free processes feature exceptional material accessibility, operational simplicity

  我们在本文中报道了在广泛的有用转化中发现的最简单氧化剂（NaH /空气）的新反应性和可能的​​机理含义，这些转化包括好氧醇氧化，烯丙醇异构化和氧化，环丙醇裂解以及直接芳基醛氧化酰胺化。这些易于实施的无过渡金属工艺具有出色的材料可及性，操作简便性和环境兼容性，并为其合成实用程序增加了新的功能，这些功能相当强大，但以前尚未完全实现和系统地探索。
• CB.sub.2 Receptor agonist compounds
  申请人：Sanofi

  公开号：US06013648A1

  公开（公告）日：2000-01-11

  The use of human CB.sub.2 receptor-specific agonists of formula (I) or (I') for preparing immunomodulating drugs is disclosed. In formulae (I) and (I'), R.sub.1 is a group selected from --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11, --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11, --CHR.sub.9 CH.sub.2 NR'.sub.6 R'.sub.11, --(CH.sub.2).sub.n Z and --COR.sub.8 ; R'.sub.1 is a --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11 or --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11 group; R.sub.2 and R'.sub.2 are hydrogen, halogen or C.sub.1-4 alkyl; R.sub.3 is hydrogen, C.sub.1-4 alkyl or a group selected from --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11, --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11 and --COR.sub.8 ; R'.sub.3 is a .dbd.CR.sub.6 R.sub.8 group; R.sub.4 has one of the meanings given for R.sub.5 or is a --COR.sub.8 group; R.sub.5 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, a halogen atom, a CF.sub.3 group, an OCF.sub.3 group or C.sub.1-4 alkylthio; R'.sub.5 has one of the meanings given for R.sub.5 and is in the 5 or 6 position of the indene ring; R.sub.6 is hydrogen or C.sub.1-4 alkyl; R'.sub.6 is C.sub.1-4 alkyl; R.sub.7 has one of the meanings given for R.sub.5 or R.sub.7 and R.sub.9 together form a --Y--CH.sub.2 -- group attached to the indole ring in the 7 position by a group Y; R.sub.8 is phenyl substituted one to four times by a substituent selected from halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; a polycyclic ring selected from naphth-1-yl, naphth-2-yl, 1,2,3,4-tetrahydronaphth-1-yl, 1,2,3,4-tetrahydronaphth-5-yl, anthryl, benzofuryl, benzothien-2-yl, benzothien-3-yl, 2-, 3-, 4- or 8-quinolyl, said polycyclic rings optionally being substituted once or twice by a substituent selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halogen, cyano, hydroxyl, trifluoromethyl and imidazol-1-yl; R.sub.10 and R.sub.11 together are a group selected from --CH.sub.2 --O--CH.sub.2 --CR.sub.12 R.sub.13 -- and --(CH.sub.2).sub.p --CR.sub.12 R.sub.13 --, wherein the carbon atom substituted by R.sub.12 and R.sub.13 is attached to the nitrogen atom; R'.sub.11 is C.sub.1-4 alkyl; or R'.sub.11 and R'.sub.6, taken together with the nitrogen atom to which they are attached, form a group selected from morpholin-4-yl, thiomorpholin-4-yl, piperidin-1-yl and pyrrolidin-1-yl; each of R.sub.12 and R.sub.13 is independently hydrogen or C.sub.1-4 alkyl; n is 2, 3, 4 or 5; p is 2 or 3; Z is a methyl group or a halogen atom; and Y is a methylene group or an oxygen atom.

  公开了使用公式（I）或（I'）的人类CB.sub.2受体特异性激动剂制备免疫调节药物。在公式（I）和（I'）中，R.sub.1是从--CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11，--(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11，--CHR.sub.9 CH.sub.2 NR'.sub.6 R'.sub.11，--(CH.sub.2).sub.n Z和--COR.sub.8中选择的一个基团；R'.sub.1是一个--CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11或--(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11基团；R.sub.2和R'.sub.2是氢，卤素或C.sub.1-4烷基；R.sub.3是氢，C.sub.1-4烷基或从--CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11，--(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11和--COR.sub.8中选择的一个基团；R'.sub.3是一个.dbd.CR.sub.6 R.sub.8基团；R.sub.4具有给出的R.sub.5的含义之一或是一个--COR.sub.8基团；R.sub.5是氢，C.sub.1-4烷基，C.sub.1-4烷氧基，卤素原子，CF.sub.3基团，OCF.sub.3基团或C.sub.1-4烷基硫基；R'.sub.5具有给出的R.sub.5的含义之一，并且位于茚环的第5或第6位置；R.sub.6是氢或C.sub.1-4烷基；R'.sub.6是C.sub.1-4烷基；R.sub.7具有给出的R.sub.5或R.sub.7的含义之一，且R.sub.9和R.sub.7一起形成一个通过Y连接到茚环的7位置的--Y--CH.sub.2--基团；R.sub.8是苯基，通过卤素，C.sub.1-4烷基或C.sub.1-4烷氧基取代一到四次；从萘-1-基，萘-2-基，1,2,3,4-四氢萘-1-基，1,2,3,4-四氢萘-5-基，蒽基，苯并呋喃基，苯并噻吩-2-基，苯并噻吩-3-基，2-, 3-, 4-或8-喹啉基中选择的多环环，所述多环环可以选择地被C.sub.1-4烷基，C.sub.1-4烷氧基，C.sub.1-4烷硫基，卤素，氰基，羟基，三氟甲基和咪唑-1-基取代一次或两次；R.sub.10和R.sub.11一起是从--CH.sub.2--O--CH.sub.2--CR.sub.12 R.sub.13--和--(CH.sub.2).sub.p--CR.sub.12 R.sub.13--中选择的一个基团，其中由R.sub.12和R.sub.13取代的碳原子连接到氮原子；R'.sub.11是C.sub.1-4烷基；或R'.sub.11和R'.sub.6，与它们连接的氮原子一起形成从吗啉-4-基，硫代吗啉-4-基，哌啶-1-基和吡咯啉-1-基中选择的一个基团；R.sub.12和R.sub.13中的每一个独立地是氢或C.sub.1-4烷基；n为2、3、4或5；p为2或3；Z为甲基基团或卤素原子；Y为亚甲基基团或氧原子。
• Copper-catalyzed efficient direct amidation of 2-methylquinolines with amines
  作者：Hao Xie、Yunfeng Liao、Shuqing Chen、Ya Chen、Guo-Jun Deng

  DOI：10.1039/c5ob00915d

  日期：——

  A copper catalyzed efficient procedure for quinoline-2-carboxamides formation via direct amidation of 2-methylquinolines under oxygen is described.

  一种铜催化的高效程序，通过在氧气下直接对2-甲基喹啉进行酰胺化，形成喹啉-2-甲酰胺。
• Sulfur–DMSO promoted oxidative coupling of active methylhetarenes with amines: access to amides
  作者：Thi Thu Tram Nguyen、Viet Dung Duong、Thi Ngoc Nga Pham、Quoc Thanh Duong、Thanh Binh Nguyen

  DOI：10.1039/d2ob01709a

  日期：——

  The elemental sulfur–DMSO couple was found to efficiently promote the oxidative coupling of active methylhetarenes with amines to yield amides under simple heating conditions. When 2-methylquinoline was used as the methylhetarene component, the formation of the expected 2-quinolinecarboxamides from anilines could be efficiently catalyzed by iron, nickel and cobalt salts. The method displayed good functional

  发现元素硫-DMSO 对在简单的加热条件下有效地促进活性甲基杂芳烃与胺的氧化偶联生成酰胺。当使用 2-甲基喹啉作为甲基杂芳烃组分时，铁盐、镍盐和钴盐可以有效地催化苯胺生成预期的 2-喹啉甲酰胺。该方法表现出良好的官能团耐受性，适用于芳香胺、杂芳香胺和脂肪胺。其他底物，如苯乙酸、二苄基二硫化物和苄胺，可以代替甲基杂环烯作为有效的伙伴。
• Colautti; Rubessa; Vio, Farmaco, Edizione Scientifica, 1981, vol. 36, # 4, p. 274 - 282
  作者：Colautti、Rubessa、Vio

  DOI：——

  日期：——