methyl 2-hydroxy-5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate | 1412888-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 2-hydroxy-5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: methyl 2-hydroxy-6-methoxy-3-oxo-1H-indene-2-carboxylate
• CAS: 1412888-70-0
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: KTHHZARBOQNQDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of indoxacarb analogs as voltage-gated sodium channel blocker

  摘要：

  Indoxacarb, the first commercialized pyrazoline-type sodium-channel blocker, is a commonly used insecticide because of high selectivity. To discover sodium-channel blocker with high insecticidal activity, a series of novel indoxacarb analogs were designed and synthesized by judicious structural modifications of the substituent group of C-5, C-6 in indenone and C-4' in benzene ring. Some analogs exhibited significant insecticidal activities against Spodoptera litura F. and excellent BgNav1-1a channel inhibitory activity. The structure-activity analysis indicated that the presence of strong electron-withdrawing group and decreased steric hindrance of indenone ring (R-1, R-2) in 5- and 6-position could enhance larvicidal activity and BgNav1-1a channel inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.058
• 作为产物：
  描述：

  5-甲氧基-1-茚酮 在 氧气 、 sodium hydride 、 potassium hydrogencarbonate 作用下， 以 水 、 乙腈 、 mineral oil 为溶剂， 30.0~80.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 methyl 2-hydroxy-5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  分子氧包埋的金纳米团簇催化 1,3-二羰基化合物的α-羟基化

  摘要：

  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...

  DOI：

  10.1246/cl.2012.976

文献信息

• Ligand Modification of Au₂₅ Nanoclusters for Near-Infrared Photocatalytic Oxidative Functionalization
  作者：Shuxin Wang、Li Tang、Baogui Cai、Zhengmao Yin、Yangfeng Li、Lin Xiong、Xi Kang、Jun Xuan、Yong Pei、Manzhou Zhu

  DOI：10.1021/jacs.2c01570

  日期：2022.3.9

  The inorganic–organic interface between metal catalysts and their substrates greatly influences reaction processes, but few studies of this interface have been conducted for a detailed understanding of its structure. Herein, we describe the synthesis and structural determination of an arylthiolated Au25(F-Ph)18– nanocluster and characterize in detail the key roles of its ligands in photocatalyzed oxidative

  金属催化剂与其底物之间的无机-有机界面对反应过程有很大影响，但很少有人对该界面进行研究以详细了解其结构。在这里，我们描述了芳硫醇化 Au 25 (F-Ph) 18的合成和结构测定——纳米团簇并详细描述了其配体在光催化氧化功能化反应中的关键作用。最重要的发现是（i）在配体之间建立相互作用以避免几何结构的扭曲，限制 Jahn-Teller 效应，并保护纳米团簇免受氧化和（ii）低能隙（HOMO-LUMO）合成簇能够通过近红外光（850 nm）实现三种类型的光催化氧化功能化反应。
• Transition-metal, organic solvent and base free α-hydroxylation of β-keto esters and β-keto amides with peroxides in water
  作者：Yakun Wang、Shuaifei Wang、Qinghe Gao、Luohao Li、Haoyu Zhi、Tao Zhang、Jixia Zhang

  DOI：10.1016/j.tet.2019.06.011

  日期：2019.7

  facile, economical and environmentally friendly strategy has been developed for the α-hydroxylation of β-keto esters and β-keto amides with peroxides via radical cross-coupling reaction in water under open-air conditions. This protocol allows a convenient access to various α-hydroxy-β-keto esters and α-hydroxy-β-keto amides with up to 92% yield (34 examples). Moreover, the reaction was successfully

  在不使用任何过渡金属，有机溶剂和碱的情况下，已开发出一种简便，经济和环保的策略，可在水中在开放的条件下通过自由基交叉偶联反应将β-酮酯和β-酮酰胺与过氧化物进行α-羟基化。空调。该方案允许以高达92％的收率方便地获得各种α-羟基-β-酮酯和α-羟基-β-酮酰胺（34个实例）。此外，反应已成功扩大至克量，机理研究表明自由基途径参与了该羟基化反应。
• 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 and structure–activity relationship of indoxacarb analogs as voltage-gated sodium channel blocker
  作者：Wenbo Hao、Chunling Fu、Huijuan Yu、Jian Chen、Hanhong Xu、Guang Shao、Dingxin Jiang

  DOI：10.1016/j.bmcl.2015.08.058

  日期：2015.10

  Indoxacarb, the first commercialized pyrazoline-type sodium-channel blocker, is a commonly used insecticide because of high selectivity. To discover sodium-channel blocker with high insecticidal activity, a series of novel indoxacarb analogs were designed and synthesized by judicious structural modifications of the substituent group of C-5, C-6 in indenone and C-4' in benzene ring. Some analogs exhibited significant insecticidal activities against Spodoptera litura F. and excellent BgNav1-1a channel inhibitory activity. The structure-activity analysis indicated that the presence of strong electron-withdrawing group and decreased steric hindrance of indenone ring (R-1, R-2) in 5- and 6-position could enhance larvicidal activity and BgNav1-1a channel inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.