methyl 2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 134644-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: Methyl 2-hydroxy-1-oxo-3,4-dihydronaphthalene-2-carboxylate
• CAS: 134644-00-1
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: OJTQXBXQDKVOLE-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  349.2±42.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 水 、 magnesium iodide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到2-hydroxy-1-tetralone
  参考文献：
  名称：

  Lewis acid-promoted α-hydroxy β-dicarbonyl to α-ketol ester rearrangement

  摘要：

  The decarbomethoxylation reaction of a substituted alpha-hydroxy-alpha-carbomethoxy pentacyclic substituted ketone, used as an advanced intermediate in the synthesis of the alkaloid aspidophytine, can be effected by heating with MgI2 in CH3CN. The reaction was shown to proceed by a novel a-hydroxy beta-dicarbonyl to alpha-ketol ester rearrangement. It was possible to isolate a carbonate intermediate in 75% yield, thereby providing support for the proposed pathway. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.071
• 作为产物：
  描述：

  methyl 1-hydroxy-3,4-dihydronaphthalene-2-carboxylate 在 亚甲兰 氧气 、 三苯基膦 作用下， 以 甲醇 、 苯 为溶剂， 生成 methyl 2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  单线态氧与β-二羰基的烯醇互变异构体的反应。2-酰基和2-羰基烷氧基-3,4-二氢萘-1（2H）-ones的α-羟基化

  摘要：

  萘酚烯丙基互变异构体的染料敏化光氧化（5）得到氢过氧萘酚（6）和萘酚（7）。三苯膦将6脱氧得到羟基萘酮（8）。

  DOI：

  10.1016/0040-4039(91)80361-9

文献信息

• Magnesium Monoperphthalate (MMPP): a Convenient Oxidant for the Direct Rubottom Oxidation of Malonates, β‐Keto Esters, and Amides
  作者：Sara Meninno、Rosaria Villano、Alessandra Lattanzi

  DOI：10.1002/ejoc.202100098

  日期：2021.3.19

  Commercially available and inexpensive magnesium monoperphthalate (MMPP) was found to be an effective oxidant for the first direct Rubottom hydroxylation of α‐substituted malonates, β‐ketoesters, and β‐ketoamides, when working in ethanol at room temperature and using NaHCO3 as basic additive. The feasibility of gram scale oxidation was also demonstrated.

  当在室温下在乙醇中工作并且使用NaHCO 3作为碱性溶液时，发现市售廉价的单过苯甲酸镁（MMPP）是α-取代的丙二酸酯，β-酮酸酯和β-酮酰胺的首次直接Rubottom羟基化的有效氧化剂。添加剂。还证明了克级氧化的可行性。
• Kinetic Resolution of Oxaziridines via Chiral Bifunctional Guanidine-Catalyzed Enantioselective α-Hydroxylation of β-Keto Esters
  作者：Xiaobin Lin、Sai Ruan、Qian Yao、Chengkai Yin、Lili Lin、Xiaoming Feng、Xiaohua Liu

  DOI：10.1021/acs.orglett.6b01614

  日期：2016.8.5

  efficient kinetic resolution of racemic oxaziridines has been realized via catalytic asymmetric α-hydroxylation of available β-keto esters. In the presence of a chiral bifunctional guanidine catalyst, a variety of optically active oxaziridines and chiral α-hydroxy β-keto esters were generated with excellent results (ee’s of up to 99% and 97% and yields of up to 44% and 54%, respectively).

  通过可利用的β-酮酯的催化不对称α-羟基化，已经实现了外消旋恶唑烷的有效动力学拆分。在手性双官能胍催化剂的存在下，生成了多种旋光性恶唑烷和手性α-羟基β-酮酸酯，具有优异的结果（ee高达99％和97％，产率高达44％和54％ ， 分别）。
• 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。
• Aerobic α-hydroxylation of β-keto esters and amides by co-catalysis of SmI3 and I2 under mild base-free conditions
  作者：Shun-Ming Yu、Kai Cui、Fei Lv、Zhen-Yu Yang、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2016.05.052

  日期：2016.6

  A clean base-free α-hydroxylation of β-keto esters and amides has been developed, in which air was used as the oxygen source and SmI3 and I2 were applied as the catalysts, affording the corresponding α-hydroxylated 1,3-dicarbonyl products in good to excellent yields under mild conditions. Mechanism discussion shows that both oxygen atoms of dioxygen are utilized and incorporated into the product through

  已经开发出清洁的无碱的β-酮酯和酰胺的α-羟基化反应，其中空气用作氧气源，SmI 3和I 2被用作催化剂，得到相应的α-羟基化的1,3-在温和条件下，二羰基产品的收率好至极好。机理讨论表明，双氧的两个氧原子都被利用，并通过独特的自由基过程掺入产物中。
• 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...