N-(2-甲酰基苯基)萘-1-磺酰胺 | 646062-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-(2-甲酰基苯基)萘-1-磺酰胺
• 英文名称: Naphthalene-1-sulfonic acid (2-formyl-phenyl)-amide
• 英文别名: N-(2-Formylphenyl)naphthalene-1-sulfonamide
• CAS: 646062-94-4
• 化学式: C₁₇H₁₃NO₃S
• 分子量: 311.361
• InChiKey: BLJDJOAKTQRNFH-UHFFFAOYSA-N

物化性质

• 沸点：
  525.2±52.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-甲酰基苯基)萘-1-磺酰胺 在 [Ir(ppy)₂bpy]PF₆ 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization

  摘要：

  A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.

  DOI：

  10.1021/acs.orglett.9b01362
• 作为产物：
  描述：

  1-萘磺酰氯 在 吡啶 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 N-(2-甲酰基苯基)萘-1-磺酰胺
  参考文献：
  名称：

  Rhodium(iii)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins through C–H activation

  摘要：

  N-磺酰基-2-氨基苯甲醛在氧化性烯丙烯烯烃的还原中性条件下，经历C-H活化并高效耦合。

  DOI：

  10.1039/c4ob00704b

文献信息

• Cp*Rh^III -Catalyzed Directed Amidation of Aldehydes with Anthranils
  作者：Suvankar Debbarma、Modhu Sudan Maji

  DOI：10.1002/ejoc.201700457

  日期：2017.7.7

  towards construction of amide C–N bonds under mild conditions through rhodium(III) catalysis has been explored. Previous waste-free amidations were generally limited to the condensation of carboxylic acids and amines. In this report, we directly applied amination of the aldehyde C(sp2)–H bond to extend the scope of amidation reactions. The amination shows a wide substrates scope, and several important

  探索了在温和条件下通过铑（III）催化构建酰胺C–N键的方法。先前的无浪费的酰胺化作用通常限于羧酸和胺的缩合。在本报告中，我们直接应用了醛C（sp 2）–H键的胺化反应来扩展酰胺化反应的范围。胺化反应显示出较宽的底物范围，并且在良性反应条件下可耐受几个重要的官能团。合成的酰胺是制备各种生物活性天然产物中存在的苯并恶嗪酮衍生物的重要前体。
• Iridium- and rhodium-catalyzed C–H activation and formyl arylation of benzaldehydes under chelation-assistance
  作者：Xifa Yang、He Wang、Xukai Zhou、Xingwei Li

  DOI：10.1039/c6ob00825a

  日期：——

  Mild and efficient synthesis of benzophenones via Ir(iii)- and Rh(iii)-catalyzed, directing group-assisted formyl C–H arylation of benzaldehydes has been achieved using diaryliodonium salts, in which Rh(iii) and Ir(iii) catalysts exhibited a complementary substrate scope.

  通过使用二芳基碘鎓盐，已经实现了对苯甲醛进行Rh(iii)和Ir(iii)催化、取向基辅助的甲酰C-H芳基化的温和高效合成苯甲酮，其中Rh(iii)和Ir(iii)催化剂展示出互补的底物范围。
• Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines
  作者：Xiaoqian Liu、Yixin Lu

  DOI：10.1039/c0ob00223b

  日期：——

  A cascade aza-Michael-Henry-dehydration reaction catalyzed by quinidine-derived tertiary amine-thiourea catalyst was developed via installation of suitable electron withdrawing groups at the amino function of aniline. This strategy led to a one-step preparation of chiral 3-nitro-1,2-dihydroquinolines in high yields and with up to 90% enantiomeric excesses.

  发展了一种由奎宁衍生的三甲胺-硫脲催化剂催化的级联氮-迈克尔-亨利-脱水反应，通过在苯胺的氨基功能上引入合适的电子吸引基团。这一策略实现了在一步中高产率地制备手性3-硝基-1,2-二氢喹啉，且具有高达90%的对映体过量。
• Efficient construction of 1,2-dihydroquinoline and 1,2,3,4-tetrahydroquinoline rings using tandem Michael-aldol reaction
  作者：Kazuishi Makino、Osamu Hara、Yuko Takiguchi、Takayuki Katano、Yumiko Asakawa、Keiichiro Hatano、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2003.10.011

  日期：2003.12

  1,2-Dihydroquinolines and a 1,2,3,4-tetrahydroquinoline were efficiently constructed using tandem Michael-aldol reaction starting from N-protected o-aminobenzaldehydes and α,β-unsaturated carbonyl compounds in good yield.

  从N-保护的邻氨基苯甲醛和α，β-不饱和羰基化合物开始，采用串联Michael-aldol反应可有效地构建1,2-二氢喹啉和1,2,3,4-四氢喹啉。
• Proline-Catalyzed Diastereoselective Synthesis of Dihydroquinolinyl-Spirooxindole via Aza-Michael/Aldol Reaction
  作者：Raju Adepu、Prathama S. Mainkar、Damodar Enagandhula

  DOI：10.1055/a-2116-5517

  日期：2023.10

  An efficient diastereoselective synthesis of 1′,4′-dihydro-2′H-spiro[indoline-3,3′-quinolin]-2-one derivatives was achieved using catalytic amount of l-proline. The key reactions involved in the present tandem reaction are aza-Michael addition and aldol reaction. This atom economic reaction proceeded under mild conditions with a broad substrate scope and excellent diastereoselectivity in good to excellent

  利用催化量的我-脯氨酸。目前串联反应中涉及的关键反应是氮杂迈克尔加成和羟醛反应。该原子经济反应在温和的条件下进行，具有广泛的底物范围和优异的非对映选择性，产率良好至优异。