1-叠氮基-2-氧代-1,2-二氢-1-萘甲酸甲酯 | 251095-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-叠氮基-2-氧代-1,2-二氢-1-萘甲酸甲酯
• 英文名称: methyl 1-azido-2-oxo-1,2-dihydro-1-naphthalenecarboxylate
• 英文别名: methyl 1-azido-2-oxo-1,2-dihydronaphthalene-1-carboxylate；Methyl 1-azido-2-oxonaphthalene-1-carboxylate
• CAS: 251095-07-5
• 化学式: C₁₂H₉N₃O₃
• 分子量: 243.222
• InChiKey: HIYGFCVWLRVLSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-叠氮基-2-氧代-1,2-二氢-1-萘甲酸甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以42%的产率得到methyl 1-azido-2-hydroxy-1,2-dihydronaphthalene-1-carboxylate
  参考文献：
  名称：

  铜通过氧化脱芳香化策略催化β-萘酚的叠氮化和过氧化

  摘要：

  使用溴化铜作为催化剂已经研究了小β-萘酚的脱芳香化叠氮化和过氧化。这些反应会产生非常有价值的萘酮衍生物，例如季铵衍生物和季铵盐。

  DOI：

  10.1039/c6cc04894c
• 作为产物：
  描述：

  2-羟基-1-萘甲酸 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 生成 1-叠氮基-2-氧代-1,2-二氢-1-萘甲酸甲酯
  参考文献：
  名称：

  Radical Chain Reactions of α-Azido-β-keto Esters with Tributyltin Hydride. A Novel Entry to Amides and Lactams through Regiospecific Nitrogen Insertion

  摘要：

  A variety of acyclic and carbocyclic alpha-azido-beta-keto esters have been readily prepared from the parent dicarbonyl compounds, and their radical chain reactions with tributyltin hydride have been investigated. These reactions normally result in efficient production of alkoxycarbonyl-substituted amides and lactams and thence provide a new, useful method for regiospecific nitrogen insertion of keto ester compounds. The likely mechanism entails initial addition of tributylstannyl radical to the azido moiety to give a stannylaminyl radical, which readily undergoes intramolecular three-membered cyclization onto the ketone group to form an alkoxyl radical. The alkoxyl radical then undergoes regiospecific beta-scissian to form a stable ring-opened radical that is eventually reduced by tributyltin hydride to propagate the chain. With certain substrates, concomitant deazidation occurs to an important extent. This process, which is unusually observed in radical reactions of alkyl azides, is ascribed to addition of the stannyl radical to the terminal azido nitrogen; subsequent fragmentation of the ensuing 1,3-triazenyl adduct gives stannyl azide and a deazidated alkyl radical, resonance-stabilized by the adjacent carbonyl groups. The radical reactions of 2-azido-2-(ethoxy-carbonyl)-1-tetralone with allyltributylstannane and allyltriphenylstannane have also been investigated with the (missed) aim to achieve nitrogen insertion and concomitant allylation.

  DOI：

  10.1021/jo990837g

文献信息

• Nitrogen atom insertion into arenols to access benzazepines
  作者：Yi He、Juanjuan Wang、Tongtong Zhu、Zhaojing Zheng、Hao Wei

  DOI：10.1039/d3sc05367a

  日期：——

  Advances in site-selective molecular editing have enabled structural modification on complex molecules.

  位点选择性分子编辑技术的进步使复杂分子的结构得以改变。
• Enantioselective Copper-Catalyzed Electrophilic Dearomative Azidation of β-Naphthols
  作者：Chong-Ji Wang、Jian Sun、Wei Zhou、Jing Xue、Bing-Tao Ren、Guang-Yi Zhang、Yan-Le Mei、Qing-Hai Deng

  DOI：10.1021/acs.orglett.9b02604

  日期：2019.9.20

  The first example of copper-catalyzed enantioselective dearomative azidation of beta-naphthols using a readily available N-3-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex N-substituent were converted to the corresponding products in high yields with up to 96% ee, and chiral 1-azido-2-hydroxy-1-naphthoates were obtained with up to 90% ee under mild reaction conditions. The azides could be further transformed into the corresponding 1,2,3-triazoles smoothly via "click" reaction.
• A copper catalyzed azidation and peroxidation of β-naphthols via an oxidative dearomatization strategy
  作者：Jayaraman Dhineshkumar、Prasanjit Samaddar、Kandikere Ramaiah Prabhu

  DOI：10.1039/c6cc04894c

  日期：——

  Dearomatizative azidation and peroxidation of [small beta]-naphthols have been explored using copper bromide as a catalyst. These reactions lead to highly valuable naphthalenone derivatives such as quaternary azide derivatives and quaternary...

  使用溴化铜作为催化剂已经研究了小β-萘酚的脱芳香化叠氮化和过氧化。这些反应会产生非常有价值的萘酮衍生物，例如季铵衍生物和季铵盐。
• Radical Chain Reactions of α-Azido-β-keto Esters with Tributyltin Hydride. A Novel Entry to Amides and Lactams through Regiospecific Nitrogen Insertion
  作者：Luisa Benati、Daniele Nanni、Corrado Sangiorgi、Piero Spagnolo

  DOI：10.1021/jo990837g

  日期：1999.10.1

  A variety of acyclic and carbocyclic alpha-azido-beta-keto esters have been readily prepared from the parent dicarbonyl compounds, and their radical chain reactions with tributyltin hydride have been investigated. These reactions normally result in efficient production of alkoxycarbonyl-substituted amides and lactams and thence provide a new, useful method for regiospecific nitrogen insertion of keto ester compounds. The likely mechanism entails initial addition of tributylstannyl radical to the azido moiety to give a stannylaminyl radical, which readily undergoes intramolecular three-membered cyclization onto the ketone group to form an alkoxyl radical. The alkoxyl radical then undergoes regiospecific beta-scissian to form a stable ring-opened radical that is eventually reduced by tributyltin hydride to propagate the chain. With certain substrates, concomitant deazidation occurs to an important extent. This process, which is unusually observed in radical reactions of alkyl azides, is ascribed to addition of the stannyl radical to the terminal azido nitrogen; subsequent fragmentation of the ensuing 1,3-triazenyl adduct gives stannyl azide and a deazidated alkyl radical, resonance-stabilized by the adjacent carbonyl groups. The radical reactions of 2-azido-2-(ethoxy-carbonyl)-1-tetralone with allyltributylstannane and allyltriphenylstannane have also been investigated with the (missed) aim to achieve nitrogen insertion and concomitant allylation.