methyl 6-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate | 145615-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate
• 英文别名: 6-Methoxycarbonyl-6-hydroxy-6,7,8,9-tetrahydro-5-oxo-5H-benzocycloheptene；6-carbomethoxy-6-hydroxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one；2-methoxycarbonyl-2-hydroxy-1-benzosuberone；methyl 6-hydroxy-5-oxo-8,9-dihydro-7H-benzo[7]annulene-6-carboxylate
• CAS: 145615-17-4
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: JHFQBIHHJVSWDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 5-hydroxy-8,9-dihydro-5H-benzo[7]annulene-6-carboxylate 在 亚甲兰 氧气 、 三苯基膦 作用下， 以 乙腈 、 苯 为溶剂， 生成 methyl 6-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate
  参考文献：
  名称：

  Dye-sensitized photooxidation of 6-acyl- and 6-carboalkoxybenzocycloalken-5-ones: reaction of singlet oxygen with enolic 1,3-dicarbonyl compounds

  摘要：

  DOI：

  10.1021/jo00053a056

文献信息

• α-Hydroxylation of 1,3-Dicarbonyl Compounds Catalyzed by Polymer-incarcerated Gold Nanoclusters with Molecular Oxygen
  作者：Hiroyuki Miyamura、Shū Kobayashi

  DOI：10.1246/cl.2012.976

  日期：2012.9.5

  α-Hydroxylation of 1,3-dicarbonyl compounds was successfully catalyzed by carbon-stabilized polymer-incarcerated gold nanoclusters (PI/CB-Au). The reaction proceeded under mild conditions using mol...

  1,3-二羰基化合物的α-羟基化被碳稳定聚合物包埋的金纳米团簇（PI/CB-Au）成功催化。反应在温和的条件下进行，使用摩尔...
• Design, Synthesis, Structure, and Dehydrogenation Reactivity of a Water-Soluble <i>o</i>-Iodoxybenzoic Acid Derivative Bearing a Trimethylammonium Group
  作者：Li-Qian Cui、Zhi-Lei Dong、Kai Liu、Chi Zhang

  DOI：10.1021/ol202777h

  日期：2011.12.16

  5-Trimethylammonio-1,3-dioxo-1,3-dihydro-1λ5-benzo[d][1,2]iodoxol-1-ol anion (AIBX 1a), an o-iodoxybenzoic acid (IBX) derivative having the trimethylammonium moiety on its phenyl ring, possesses very good solubility in water and distinct oxidative properties from IBX, which is demonstrated in the oxidation of various β-keto esters to the corresponding dehydrogenated products using water as cosolvent

  5-三甲基铵基- 1,3-二氧代-1,3-二氢- 1λ 5 -苯并[ d ] [1,2] iodoxol -1-醇阴离子（AIBX 1A），一个Ô -iodoxybenzoic苯甲酸（IBX）衍生物具有在其苯环上的三甲基铵部分在水中具有非常好的溶解性，并且具有与IBX不同的氧化性能，这在使用水作为助溶剂的各种β-酮酸酯氧化为相应的脱氢产物中得到了证明。由于AIBX 1a具有良好的水溶性，因此可以从反应混合物中轻松实现其再生。
• Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines
  作者：Franklin A. Davis、Hu Liu、Bang-Chi Chen、Ping Zhou

  DOI：10.1016/s0040-4020(98)00500-6

  日期：1998.8

  The oxidation of 1,3-dicarbonyl compounds with (camphorylsulfonyl)oxaziridines 2 was studied in both cyclic and acyclic systems. Two reaction pathways were identified: enolate α-hydroxylation and a novel Baeyer-Villiger type oxidation. The Baeyer-Villiger oxidation product was observed only for the ketones and arises via rearrangement of an alkoxy epoxide. Synthetically useful ee's (82–95%) were observed

  在环状和非环状体系中都研究了（樟脑磺酰基）恶二吡啶2对1，3-二羰基化合物的氧化作用。确定了两个反应途径：烯醇化α-羟基化反应和新型Baeyer-Villiger型氧化反应。仅对酮观察到了Baeyer-Villiger氧化产物，并且是通过烷氧基环氧化物的重排而产生的。仅在酮基为6元环的一部分的β-酮酸酯的烯醇化物中观察到合成有用的ee（82–95％）。
• HYDROXYLATION OF BETA-DICARBONYLS WITH ZIRCONIUM CATALYSTS
  申请人：CASALNUOVO ALBERT LOREN

  公开号：US20080306259A1

  公开（公告）日：2008-12-11

  The present invention pertains to a process for preparing a compound of Formula I that is achiral, racemic or enantiomerically enriched at the hydroxylation center indicated by * comprising contacting a compound of Formula II with an oxidant selected from oxygen, hydrogen peroxide, peracids or alkyl hydropetoxides in the presence of a zirconium complex, wherein R 1 , R 2 and R 3 are as defined in the disclosure. This invention also pertains to zirconium complexes useful in this procedure comprising zirconium and a ligand of Formula III or its enantiomer wherein J, R 6 and n are as defined in the disclosure. This invention further pertains to a compound of Formula III or its enantiomer.

  本发明涉及一种制备公式I化合物的方法，该化合物是在羟基化中心处无手性、外消旋或对映富集的，所述方法包括将公式II化合物与氧、过氧化氢、过酸或烷基过氧化物等氧化剂在锆配合物的存在下接触，其中R1、R2和R3如本文所定义。本发明还涉及在该过程中有用的锆配合物，其包括锆和公式III配体或其对映体，其中J、R6和n如本文所定义。本发明还涉及公式III或其对映体的化合物。
• Hydroxylation of Beta-Dicarbonyls with Zirconium Catalysts
  申请人：Casalnuovo Albert Loren

  公开号：US20100185014A1

  公开（公告）日：2010-07-22

  The present invention pertains to a process for preparing a compound of Formula I that is achiral, racemic or enantiomerically enriched at the hydroxylation center indicated by * comprising contacting a compound of Formula II with an oxidant selected from oxygen, hydrogen peroxide, peracids or alkyl hydroperoxides in the presence of a zirconium complex, wherein R 1 , R 2 and R 3 are as defined in the disclosure. This invention also pertains to zirconium complexes useful in this procedure comprising zirconium and a ligand of Formula III or its enantiomer wherein J, R 6 and n are as defined in the disclosure. This invention further pertains to a compound of Formula III or its enantiomer.

  本发明涉及一种制备公式I化合物的方法，该化合物是在*处的羟基化中心上是无手性、外消旋或对映富集的，包括将公式II化合物与氧气、过氧化氢、过酸或烷基过氧化物等氧化剂在锆配合物存在下接触，其中R1、R2和R3如本文所定义。本发明还涉及在该过程中有用的锆配合物，包括锆和公式III或其对映体的配体，其中J、R6和n如本文所定义。本发明还涉及公式III或其对映体的化合物。