dithiocarbonic acid ethyl ester [2-(2-hydroxy-4-methoxy-phenyl)-2-oxo-ethyl] ester | 616892-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dithiocarbonic acid ethyl ester [2-(2-hydroxy-4-methoxy-phenyl)-2-oxo-ethyl] ester
• 英文别名: O-ethyl S-(2-(2-hydroxy-4-methoxyphenyl)-2-oxoethyl) carbonodithioate；O-ethyl [2-(2-hydroxy-4-methoxyphenyl)-2-oxoethyl]sulfanylmethanethioate
• CAS: 616892-31-0
• 化学式: C₁₂H₁₄O₄S₂
• 分子量: 286.373
• InChiKey: IQBZDPWLCWINOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid ethyl ester [2-(2-hydroxy-4-methoxy-phenyl)-2-oxo-ethyl] ester 在 吡啶 、 过氧化双月桂酰 、 乙酸酐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 33.5h， 生成 2,2-dimethyl-propionic acid 5-hydroxy-7-methoxy-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Total Synthesis of 10-Norparvulenone and of O-Methylasparvenone Using a Xanthate-Mediated Free Radical Addition−Cyclization Sequence

  摘要：

  A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.

  DOI：

  10.1021/ol035394o
• 作为产物：
  描述：

  3-甲氧基苯酚 在 三氯化铝 作用下， 以 二硫化碳 、 丙酮 为溶剂， 反应 2.0h， 生成 dithiocarbonic acid ethyl ester [2-(2-hydroxy-4-methoxy-phenyl)-2-oxo-ethyl] ester
  参考文献：
  名称：

  Total Synthesis of 10-Norparvulenone and of O-Methylasparvenone Using a Xanthate-Mediated Free Radical Addition−Cyclization Sequence

  摘要：

  A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.

  DOI：

  10.1021/ol035394o

文献信息

• A radical-based approach to hydroxytetralones from unprotected phenols
  作者：Laurent Petit、Samir Z. Zard

  DOI：10.1039/c0cc00680g

  日期：——

  Xanthates derived from unprotected 2-hydroxyacetophenones undergo smooth intermolecular addition to unactivated alkenes and subsequent cyclisation to give hydroxytetralones in good yield.

  未受保护的2-羟基乙酰苯酮衍生的黄原酸盐能够顺利地对非活化烯烃进行分子间加成，随后环化生成高产率的羟基四氢萘酮。
• Facile Synthesis of β-Keto Sulfones Employing Fenton’s Reagent in DMSO
  作者：Vladimir Abaev、Olga Serdyuk、Petrakis Chalikidi、Maxim Uchuskin、Igor Trushkov

  DOI：10.1055/s-0036-1589151

  日期：2018.3

  A new facile method for the synthesis of β-keto sulfones employing xanthates, DMSO, and Fenton’s reagent is described. The reaction proceeds under very mild conditions providing a cost-effective straightforward approach to various β-keto sulfones in high yields.

  描述了一种使用黄原酸盐、DMSO 和 Fenton 试剂合成 β-酮砜的新方法。该反应在非常温和的条件下进行，为高产率的各种 β-酮砜提供了一种具有成本效益的直接方法。
• Radical Instability in Aid of Efficiency: A Powerful Route to Highly Functional MIDA Boronates
  作者：Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/jacs.5b03893

  日期：2015.6.3

  The inability of the sp(3) boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array Of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical Stabilization also allows the exchange Of the Xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.
• Total Synthesis of 10-Norparvulenone and of <i>O</i>-Methylasparvenone Using a Xanthate-Mediated Free Radical Addition−Cyclization Sequence
  作者：Alejandro Cordero Vargas、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ol035394o

  日期：2003.10.1

  A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.