2-amino-6-methylbenzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-6-methylbenzaldehyde
• 化学式: C₈H₉NO
• mdl: MFCD18389805
• 分子量: 135.166
• InChiKey: FETAMGUXMBZISE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-6-methylbenzaldehyde 在 甲烷磺酸 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 6,7-didehydro-5',17-dimethylquinolino[2',3':6,7]morphinan-3,14β-diol
  参考文献：
  名称：

  Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

  摘要：

  We have reported previously the novel delta opioid agonist KNT-127 which showed high affinity and selectivity for the delta receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical delta agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5'-, 6'-, 7'- or 8'-position of the quinoline ring and revealed that many derivatives with 5'- or 8'-substituents showed high affinities and selectivities for the delta receptor. Especially, SYK-153 with an 8'-OH group showed the highest affinity and the most balanced and highest selectivity for the delta receptor among the synthesized compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.004
• 作为产物：
  描述：

  (2-amino-6-methylphenyl)methanol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以83%的产率得到2-amino-6-methylbenzaldehyde
  参考文献：
  名称：

  通过一锅串联 Oxa-Michael-Aldol 序列轻松获得 Quinolin-2(1H)-ones

  摘要：

  已开发出一种合成多种喹啉-2(1H)-one 衍生物的有效策略。该反应从肉桂酰胺衍生物在NaOH存在下通过串联反应进行，以良好至极好的产率提供相应的2-喹啉-2(1H)-酮衍生物。

  DOI：

  10.1055/s-0036-1588470

文献信息

• Anti-ulcerative imidazopyridine compounds
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US04920129A1

  公开（公告）日：1990-04-24

  The invention relates to an imidazopyridine compound of the following formula: ##STR1## wherein R.sup.1 is lower alkynyl, R.sup.2 is lower alkyl, R.sup.3 is lower alkyl, R.sup.4 is amino or acylamino, R.sup.5 is hydrogen; lower alkyl which may be substituted by halogen, halogen; nitro; amino; acylamino; esterified carboxy; or N,N-di(lower)alkylsufamoyl, and A is lower alkylene, and pharmaceutically acceptable salts thereof, useful in the treatment of ulcers.

  该发明涉及以下结构的咪唑吡啶化合物：##STR1##其中R.sup.1为较低的炔基，R.sup.2为较低的烷基，R.sup.3为较低的烷基，R.sup.4为氨基或酰胺基，R.sup.5为氢；较低的烷基，可能被卤素取代，卤素；硝基；氨基；酰胺基；酯化羧基；或N，N-二(较低)烷基磺酰基，A为较低的烷基，以及其药学上可接受的盐，用于治疗溃疡。
• Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs
  作者：Monroe E. Wall、Mansukh C. Wani、Allan W. Nicholas、Govindarajan Manikumar、Chhagan Tele、Linda Moore、Anne Truesdale、Peter Leitner、Jeffrey M. Besterman

  DOI：10.1021/jm00070a013

  日期：1993.9

  A large number of camptothecin (CPT) analogs have been prepared in the 20S, 20RS, and 20R configurations with a number of ring A substituents. Topoisomerase I (T-I) inhibition data (IC50) have been obtained by standard procedures. In general, substitution at the 9 or 10 positions with amino, halogeno, or hydroxyl groups in compounds with 20S configuration results in compounds with enhanced T-I inhibition

  已经制备了具有许多环A取代基的20S，20RS和20R构型的大量喜树碱（CPT）类似物。拓扑异构酶I（TI）抑制数据（IC50）已通过标准程序获得。通常，具有20S构型的化合物在9或10位上被氨基，卤代或羟基取代会导致TI抑制作用增强。20RS构型的化合物在体外和体内活性较低，而20R构型的化合物则无活性。在TI抑制试验中，在A环上具有10,11-亚甲二氧基取代的化合物显示出显着的效能增强。在包括L-1210小鼠白血病测定法在内的各种体内测定法中确定的某些类似物的活性通常与TI抑制作用一致。制备了许多水溶性类似物，例如20-甘氨酸酯，9-甘氨酰胺或水解的内酯盐，并在体外和体内试验中进行了测试。通常，就L-1210分析中的TI抑制作用和寿命延长而言，这些化合物的活性均不如CPT。然而，某些20-甘氨酸酯在静脉内给药后显示出良好的体内活性。
• Catalytic Asymmetric Cascade Using Spiro-Pyrrolidine Organocatalyst: Efficient Construction of Hydrophenanthridine Derivatives
  作者：Jin-Miao Tian、Yong-Hai Yuan、Yu-Yang Xie、Shu-Yu Zhang、Wen-Qiang Ma、Fu-Min Zhang、Shao-Hua Wang、Xiao-Ming Zhang、Yong-Qiang Tu

  DOI：10.1021/acs.orglett.7b03330

  日期：2017.12.15

  (spiro-pyrrolidine) organocatalyst has been demonstrated to enable an asymmetric aza-Michael/Michael/aldol cyclization cascade, in which two six-membered rings (B/C) and three stereocenters have been constructed in a catalytic one-step process. It is so far the most efficient method for construction of hydrophenanthridine derivatives featuring high enantioselectivity. The trans- or cis-fused B/C-rings

  已证明新开发的SPD（螺吡咯烷）有机催化剂可实现不对称的aza-Michael / Michael / aldol环化级联反应，在该催化反应中，两个六元环（B / C）和三个立体中心被构建步骤过程。迄今为止，这是构建具有高对映选择性的氢菲啶衍生物的最有效方法。的反式-或顺式-融合B / C环可以选择性地在一个基片控制的方式组装。此外，该级联反应可以放大至克级，而不会损失对映选择性。
• Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources
  作者：Di Hu、Chao Pi、Wei Hu、Xiliang Han、Yangjie Wu、Xiuling Cui

  DOI：10.1016/j.cclet.2021.12.072

  日期：2022.8

  N-O bond cleavage and fragmentation. Variously substituted (especially 6- or 7-substituted) quinolines could be easily afforded. This procedure features wide functional group compatibility, efficiency and avoiding toxic cyano source. Meanwhile, this protocol could be successfully applied to scale-up synthesis. Further chemical transformations of 3-cyanoquinoline could give some valuable skeletons, demonstrating

  开发了 Ru(Ⅲ) 催化的 2-氨基芳香醛（酮）和异恶唑的环化反应，得到多种 3-氰基喹啉。值得注意的是，异恶唑通过NO 键断裂和断裂充当环化试剂和无毒氰基源。可以很容易地提供各种取代（尤其是 6 或 7 取代）的喹啉。该程序具有广泛的官能团兼容性、效率和避免有毒氰基源。同时，该协议可以成功地应用于放大合成。3-氰基喹啉的进一步化学转化可以产生一些有价值的骨架，证明其在合成应用中的潜力
• Metal free carboamination of internal alkynes – an easy access to polysubstituted quinolines
  作者：T. Stopka、M. Niggemann

  DOI：10.1039/c5cc10460b

  日期：——

  A transition metal free carboamination of unactivated alkynes towards highly substituted quinolines was realized in the presence of a synergistic Bronsted acid based catalyst system. The mechanism was confirmed to...

  在协同的布朗斯台德酸基催化剂体系的存在下，实现了未活化的炔烃向高度取代的喹啉的无过渡金属无碳氨化反应。该机制被确认为...