6-methyl-1,2-dihydroquinoline | 97531-28-7

• 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: 6-methyl-1,2-dihydroquinoline
• CAS: 97531-28-7
• 化学式: C₁₀H₁₁N
• mdl: MFCD19217433
• 分子量: 145.204
• InChiKey: LUVSSHMDUIBQQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C
• 沸点：
  262.0±40.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-methyl-1,2-dihydroquinoline 在 sodium hydrogen sulfate 、 CrO₂^(1-)*Na⁽¹⁺⁾ 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 生成 6-甲基喹啉
  参考文献：
  名称：

  OXIDATION OF 1,2-DIHYDROQUINOLINES UNDER MILD AND HETEROGENEOUS CONDITIONS

  摘要：

  A combination of NaHSO4.H2O and Na2Cr2O7.2H(2)O in the presence Of Wet SiO2 were used as an effective oxidizing agent for the oxidation of 1,2-dihydroquinolines to their corresponding quinoline derivatives in dichloromethane at room temperature with excellent yields.

  DOI：

  10.1081/scc-100105895
• 作为产物：
  描述：

  6-甲基喹啉 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 6-methyl-1,2-dihydroquinoline
  参考文献：
  名称：

  Heteroatom-Guided, Palladium-Catalyzed Regioselective C–H Functionalization in the Synthesis of 3-Arylquinolines

  摘要：

  A new approach for the regioselective functionalization of the C-3-position of quinolines is described. The method utilizes heteroatom guided regioselective C-3 palladation followed by arylation via transmetalation with aryl boronic acids to yield 3-aryl-N-acyl-1,2-dihydroquinolines. In a one-pot sequence, N-deacylation followed by aromatization leads to important 3-arylquinolines in good yields.

  DOI：

  10.1021/ol401349a

文献信息

• Enantioselective Synthesis of 4-Aminotetrahydroquinolines via 1,2-Reductive Dearomatization of Quinolines and Copper(I) Hydride-Catalyzed Asymmetric Hydroamination
  作者：Qing-Feng Xu-Xu、Xiao Zhang、Shu-Li You

  DOI：10.1021/acs.orglett.9b02034

  日期：2019.7.5

  1,2-reductive dearomatization of quinolines and copper(II) acetate monohydrate/(R,R)-Ph-BPE/P(p-tolyl)3-catalyzed enantioselective hydroamination sequence was developed, affording diverse 4-amino-1,2,3,4-tetrahydroquinolines with high levels of enantioselectivity in either a stepwise or one-pot fashion. Pleasingly, internal cis-cyclic alkenes, which are challenging substrates in copper hydride-catalyzed

  开发了喹啉和一水合乙酸铜（II）/（R，R）-Ph-BPE / P（对甲苯基）3-催化的对映选择性加氢胺化反应的1,2-还原脱芳香化反应，提供了多种4-氨基-1，具有高对映选择性的2,3,4-四氢喹啉，呈逐步或一锅方式。令人愉快的是，在氢化铜催化的对映选择性加氢胺化反应中具有挑战性的底物内部顺式环烯烃在温和条件下得到了有效转化。
• [EN] AUREOBASIDIUM DERIVATIVES AND METHODS OF SYNTHESIS<br/>[FR] DÉRIVÉS D'AUREOBASIDIUM ET PROCÉDÉS DE SYNTHÈSE
  申请人：AUREOGEN BIOSCIENCES INC

  公开号：WO2018031521A1

  公开（公告）日：2018-02-15

  In general, the invention relates to AbA derivatives that are useful for treating infection. These novel compounds are shown to be effective in treating various fungal infections. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various fungal infections.

  一般而言，本发明涉及用于治疗感染的AbA衍生物。这些新颖的化合物被证明在治疗各种真菌感染方面是有效的。本发明还提供了包含该化合物的药学上可接受的组合物以及使用该组合物治疗各种真菌感染的方法。
• SUBSTITUTED PICOLINAMIDE KINASE INHIBITORS
  申请人：Portola Pharmaceuticals, Inc.

  公开号：US20140113931A1

  公开（公告）日：2014-04-24

  Provided are picolinamide compounds for inhibiting of Syk kinase, intermediates used in making such compounds, methods for their preparation, pharmaceutical compositions thereof, methods for inhibiting Syk kinase activity, and methods for treating conditions mediated at least in part by Syk kinase activity.

  提供了用于抑制Syk激酶的吡啶甲酰胺化合物，制备这种化合物所使用的中间体，制备这种化合物的方法，制备药物组成物的方法，抑制Syk激酶活性的方法以及治疗至少部分通过Syk激酶活性介导的疾病的方法。
• BICYCLIC OXA-LACTAM KINASE INHIBITORS
  申请人：PORTOLA PHARMACEUTICALS, INC.

  公开号：US20150252056A1

  公开（公告）日：2015-09-10

  Provided are bicyclic oxa-lactam compounds for inhibition of JAK/Syk kinase, intermediates used in making such compounds, methods for their preparation, pharmaceutical compositions thereof, methods for inhibiting JAK/Syk kinase activity, and methods for treating conditions mediated at least in part by JAK/Syk kinase activity.

  提供了双环氧内酰胺化合物，用于抑制JAK/Syk激酶，用于制备这种化合物的中间体，其制备方法，制备这种化合物的制药组合物，抑制JAK/Syk激酶活性的方法，以及治疗至少部分由JAK/Syk激酶活性介导的疾病的方法。
• Ruthenium‐Catalyzed Regioselective 1,2‐Hydrosilylation of N‐Heteroarenes
  作者：Xinyuan Ma、Manoj V. Mane、Luigi Cavallo、Steven P. Nolan

  DOI：10.1002/ejoc.202201466

  日期：2023.3.7

  An efficient method for the regioselective 1,2-hydrosilylation of N-heteroarenes is reported employing ruthenium complex [RuCl(PPh3)2(η5-(3-phenylindenylidene))] as catalyst. The developed protocol provides the efficient dearomatization of a broad range of substituted quinolines and related N-heteroarenes at low catalyst loading under mild conditions. A plausible mechanism is probed through stoichiometric

  报道了一种使用钌络合物 [RuCl(PPh 3 ) 2 (η 5 -(3-phenylindenylidene))] 作为催化剂对 N-杂芳烃进行区域选择性 1,2-氢化硅烷化的有效方法。所开发的协议可在温和条件下以低催化剂负载量对广泛的取代喹啉和相关的 N-杂芳烃进行有效的脱芳构化。通过化学计量反应和 DFT 计算探索了一种似是而非的机制。