methyl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate | 51737-05-4

• 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-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: 2-Hydroxy-2-carbomethoxyindanon；methyl 2-hydroxy-3-oxo-1H-indene-2-carboxylate
• CAS: 51737-05-4
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: VDOINBMNOYWSMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-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：

  1H-茚-2-甲酸,2,3-二氢-1-氧代-,甲酯 在 氧气 、 异丁醛 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以70%的产率得到methyl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  与介孔氮化碳相连的分子钴催化剂实现高效的光催化有氧氧化

  摘要：

  绿色和可持续氧化反应的发展需要高效的催化剂来利用分子氧作为末端氧化剂。在目前的工作中，通过将钴分子络合物作为电子转移介质通过酰胺键共价接枝到介孔氮化碳上，合理地设计了一种特定的杂化光催化剂。这种纳米结构的双功能光催化剂通过各种光谱技术进行了表征，并被证明是一种选择性且有效的催化剂，可用于光催化可见光驱动的有机分子有氧氧化。该策略提供了分子催化剂和半导体材料之间的有效电子通信，因此为化学合成中的光催化有氧氧化开辟了一条途径。

  DOI：

  10.1016/j.catcom.2022.106498

文献信息

• Reactivity of Hydroxy- and Aquo(hydroxy)-λ³-iodane-Crown Ether Complexes
  作者：Kazunori Miyamoto、Yukie Yokota、Takashi Suefuji、Kentaro Yamaguchi、Tomoyuki Ozawa、Masahito Ochiai

  DOI：10.1002/chem.201304961

  日期：2014.4.25

  designed a series of hydroxy(aryl)‐λ3‐iodane–[18]crown‐6 complexes, prepared from the corresponding iodosylbenzene derivatives and superacids in the presence of [18]crown‐6, and have investigated their reactivities in aqueous media. These activated iodosylbenzene monomers are all non‐hygroscopic shelf‐storable reagents, but they maintain high oxidizing ability in water. The complexes are effective for

  我们已经设计了一系列羟基（芳基）的-λ 3 -iodane- [18]冠-6配合物，从在存在相应的亚碘酰苯衍生物和超酸制备[18]冠-6，并在含水研究了它们的反应性媒体。这些活化的碘烷基苯单体都是非吸湿性的可货架存储的试剂，但是它们在水中具有很高的氧化能力。该络合物可在温和条件下有效氧化苯酚，硫化物，烯烃，甲硅烷基烯醇醚和烷基（三氟）硼酸酯。此外，羟基λ 3 -iodane- [18]冠-6配合物作为有效祖细胞为的二芳基- ，乙烯基-的合成，和炔基- λ 3水中的碘。在某些情况下，也可以使用其他极性较小的有机溶剂，例如甲醇，乙腈和二氯甲烷。
• A Simple and Effective Method for α-Hydroxylation of β-Dicarbonyl Compounds Using Oxone as an Oxidant without a Catalyst
  作者：Jun Yu、Jian Cui、Chi Zhang

  DOI：10.1002/ejoc.201000940

  日期：2010.12

  Oxone has been found to be a highly efficient reagent for the introduction of a hydroxy group at the α position of a variety of β-dicarbonyl compounds in the homogeneous solvent mixture of water and 1,4-dioxane at 60 °C.

  已发现 Oxone 是一种高效试剂，可在 60 °C 下在水和 1,4-二恶烷的均相溶剂混合物中在各种 β-二羰基化合物的 α 位引入羟基。
• Visible light-mediated selective α-functionalization of 1,3-dicarbonyl compounds <i>via</i> disulfide induced aerobic oxidation
  作者：Jingnan Zhao、Fan Yang、Zongyi Yu、Xiaofei Tang、Yufeng Wu、Cunfei Ma、Qingwei Meng

  DOI：10.1039/c9cc06544j

  日期：——

  A visible light-mediated α-functionalization of 1,3-dicarbonyl compounds with switchable selectivity induced by disulfide is disclosed. Upon irradiation with visible light, the metal- and base-free α-hydroxylation or α-hydroxymethylation reaction proceeded smoothly through a disulfide-catalyzed oxidation under mild conditions. The combination of a continuous-flow strategy could further improve the

  公开了可见光介导的1，3-二羰基化合物的α-官能化，其具有由二硫化物诱导的可选择性切换。在可见光照射下，无金属和无碱的α-羟基化或α-羟甲基化反应在温和的条件下通过二硫键催化的氧化反应顺利进行。连续流策略的组合可以进一步提高反应效率。
• Cu(I)-catalyzed asymmetric α-hydroxylation of β-keto esters in the presence of chiral phosphine-Schiff base-type ligands
  作者：Jia-Jun Jiang、Jian Huang、De Wang、Mei-Xin Zhao、Fei-Jun Wang、Min Shi

  DOI：10.1016/j.tetasy.2010.05.011

  日期：2010.4

  Chiral phosphine-Schiff base-type ligand L1 prepared from (R)-(−)-2-(diphenylphosphino)-1,1′-binaphthyl-2′-amine was found to be a fairly effective ligand for Cu(I)-promoted enantioselective α-hydroxylation of β-keto esters using oxaziridine 2a as the oxidant to give the corresponding products in high yields along with moderate enantioselectivities.

  发现由（R）-（-）-2-（二苯基膦基）-1,1'-联萘基-2'-胺制备的手性膦-席夫碱型配体L1是Cu（I）-的相当有效的配体恶唑烷2a作为氧化剂促进β-酮酯的对映选择性α-羟基化，从而以高收率和适度的对映选择性提供相应的产物。
• 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％）。