2-azido-5-methoxybenzaldehyde | 908242-31-9

• 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-azido-5-methoxybenzaldehyde
• CAS: 908242-31-9
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: KOGSIHPWVRMULR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-5-methoxybenzaldehyde 在 manganese(IV) oxide 、 gold(III) chloride 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 3,6-dimethoxy-2-methylquinolin-4(1H)-one
  参考文献：
  名称：

  Gold(iii)-catalyzed azide-yne cyclization/O–H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks

  摘要：

  已开发出一种以金为催化剂的级联反应，可快速合成3-烷氧基-4-喹啉，并应用于生物碱合成。

  DOI：

  10.1039/d0ob00745e
• 作为产物：
  描述：

  (2-Azido-5-methoxyphenyl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以1.1 g的产率得到2-azido-5-methoxybenzaldehyde
  参考文献：
  名称：

  Discovery of Novel Tricyclic Full Agonists for the G-Protein-Coupled Niacin Receptor 109A with Minimized Flushing in Rats

  摘要：

  Tricyclic analogues were rationally designed as the high affinity niacin receptor G-protein-coupled receptor 109A (GPR109A) agonists by overlapping three lead structures. Various tricyclic anthranilide and cycloalkene carboxylic acid full agonists were discovered with excellent in vitro activity. Compound 2g displayed a good therapeutic index regarding free fatty acids (FFA) reduction and vasodilation effects in rats, with very weak cytochrome P450 2C8 (CYP2C8) and cytochrome P450 2C9 (CYP2C9) inhibition, and a good mouse pharmacokinetics (PK) profile.

  DOI：

  10.1021/jm900151e

文献信息

• Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from<i>N</i>¹-Alkyne-1,2-diamines
  作者：Ravi Kumar、Rajesh K. Arigela、Srinivas Samala、Bijoy Kundu

  DOI：10.1002/chem.201502956

  日期：2015.12.14

  oriented synthesis of two N‐polyheterocycles indoloazepinobenzimidazole and benzimidazotriazolobenzodiazepine from a common N1‐alkyne‐1,2‐diamine building block is described. The approach involves sequential formation of benzimidazole through cyclocondensation and oxidation, which is followed by the formation of either an azepine ring (through alkyne activation and 6‐endo‐dig cyclization, 1,2‐migration

  描述了一种从一个常见的N 1-炔烃1,2-二胺结构单元合成两个N杂环的吲哚并氮杂三唑并苯并咪唑三唑并苯并二氮杂pine的一站式实验方案。该方法涉及通过环缩合和氧化顺序形成苯并咪唑，然后形成氮杂环（通过炔烃活化和6-内挖-环化，1,2-环扩环迁移和再芳构化）， 1,3-偶极环加成反应生成二氮杂或三唑环。
• One-pot synthesis of dihydroquinazolinethione-based polycyclic system
  作者：Wensheng Zhang、Xiaofeng Zhang、Xiaoming Ma、Wei Zhang

  DOI：10.1016/j.tetlet.2018.09.023

  日期：2018.10

  A one-pot and diastereoselective synthesis of quinazoline-2(1H)-thione-containing polycyclic compounds is introduced. The reaction process includes [3 + 2] cycloaddition of azomethine ylides for pyrrolidines, Staudinger-aza-Wittig reaction of azides for iminophosphoranes, formation of isothiocyanates, and finally cyclization of amines to isothiocyanates for dihydroquinazolinethiones.

  介绍了一锅和非对映选择性合成的含喹唑啉-2（1 H）-硫酮的多环化合物。反应过程包括对吡咯烷类化合物进行[3 + 2]环加成反应，将叠氮基的Staudinger-Aza-Wittig反应生成亚氨基正膦，形成异硫氰酸酯，最后将胺环化为异硫氰酸酯，形成二氢喹唑啉硫酮。
• Reaction of the Morita-Baylis-Hillman Acetates of 2-Azidobenzaldehydes with Triethyl Phosphite: Synthesis of 1-Diethylphosphono-1,2-dihydro­quinolines and 3-Acetoxymethylquinolines
  作者：Kee-Jung Lee、Hyung-Woo Yi、Hyun Park、Young Song

  DOI：10.1055/s-2006-942383

  日期：2006.6

  A simple synthesis of l-diethylphosphono-1,2-dihydro-quinolines and 3-acetoxymethylquinolines from the reaction of several Morita-Baylis-Hillman acetates of 2-azidobenzaldehydes with triethyl phosphite has been described.

  已经描述了由 2-叠氮基苯甲醛的几种 Morita-Baylis-Hillman 乙酸酯与亚磷酸三乙酯的反应简单合成 1-二乙基膦酰基-1,2-二氢喹啉和 3-乙酰氧基甲基喹啉。
• Quinolines from Morita–Baylis–Hillman acetates of 2-azidobenzaldehydes
  作者：Eun-Gu Han、Hea Jung Kim、Kee-Jung Lee

  DOI：10.1016/j.tet.2009.09.047

  日期：2009.11

  A simple method for synthesizing several 2-alkoxy-3-arylsulfinylmethylquinolines using an aza-Wittig type reaction of 3-(2-azidophenyl)-2-(arylsulfinylmethyl)propenoates, which were readily obtained from the Morita–Baylis–Hillman acetates of 2-azidobenzaldehydes, has been developed.

  一种简单的方法，可使用3-（2-叠氮基苯基）-2-（芳基亚砜基甲基）丙酸酯的氮杂-Wittig型反应合成数种2-烷氧基-3-芳基亚砜基甲基喹啉，这些化合物很容易从Morita-Baylis-Hillman乙酸盐中获得，为2 -叠氮苯甲醛已被开发。
• Silver‐Catalyzed Carbocyclization of Azide‐Tethered Alkynes: Expeditious Synthesis of Polysubstituted Quinolines
  作者：Xinfang Xu、Han Su、Ming Bao、Jingjing Huang、Lihua Qiu

  DOI：10.1002/adsc.201801425

  日期：——

  A silver‐catalyzed carbocyclization of azide‐tethered alkynes has been developed for the synthesis of polysubstituted quinolines in good to high yields. Mechanistic studies indicate that this reaction is initiated by a silver‐catalyzed 6‐endo‐dig azide‐yne cyclization, followed by a formal R−X (X=Cl, Br, or I) insertion with external halide through a ylide intermediate. The salient features of this

  已开发出一种银催化的叠氮化物束缚炔烃的碳环化反应，以高产率到高产率合成多取代的喹啉。机理研究表明，该反应是由银催化的6-内切-叠氮叠氮炔环化反应引发的，随后是正式的RX（X = Cl，Br或I）与外部卤化物通过叶立德中间体插入。该反应的显着特征包括容易获得的材料，廉价的银催化剂，温和的反应条件，良好的官能团耐受性和易于进一步转化的特点。