(±)-1,1-dioxo-3,4-dihydro-2H-thiochromen-4-ol | 2765-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: (±)-1,1-dioxo-3,4-dihydro-2H-thiochromen-4-ol
• 英文别名: 1,1-dioxo-1-thiochroman-4-ol；1,1-dioxo-1λ⁶-thiochroman-4-ol；4-Hydroxythiochroman 1,1-dioxide；1,1-dioxo-3,4-dihydro-2H-thiochromen-4-ol
• CAS: 2765-44-8
• 化学式: C₉H₁₀O₃S
• mdl: MFCD12047732
• 分子量: 198.243
• InChiKey: HDWSBBCZEGJIPK-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97 °C
• 沸点：
  423.2±45.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 (±)-1,1-dioxo-3,4-dihydro-2H-thiochromen-4-ol 在 Burkholderia cepacia Amano-PS lipase; immobilized on diatomaceous earth 作用下， 以 甲基叔丁基醚 为溶剂， 以40%的产率得到(4S)-1,1-dioxo-3,4-dihydro-2H-thiochromen-4-ol
  参考文献：
  名称：

  Enzymatic resolution of chroman-4-ol and its core analogues with Burkholderia cepacia lipase

  摘要：

  A convenient protocol for lipase resolution of chroman-4-ol and its analogues (six- and seven-membered rings with O, S, SO2) has been elaborated. The structure of substrates has minor influence on the efficiency of resolution. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.010
• 作为产物：
  描述：

  硫代-3,4-二氢苯并吡喃-4-醇 在 (PF6)2 、 高碘酸 作用下， 以 吡啶 为溶剂， 以85%的产率得到(±)-1,1-dioxo-3,4-dihydro-2H-thiochromen-4-ol
  参考文献：
  名称：

  双核锰配合物作为催化剂将硫化物选择性有效地氧化为砜

  摘要：

  在温和条件下，双核Mn IV complexMn IV锰络合物1催化硫化物的高碘酸氧化为砜。发现该反应是高度选择性的，即使在存在其他易于氧化的基团的情况下，也给出了几乎定量的砜收率。仅发现胺会阻碍反应。

  DOI：

  10.1016/s0040-4039(98)01518-4

文献信息

• <i>ansa</i>-Ruthenium(II) Complexes of R₂NSO₂DPEN-(CH₂)_n(η⁶-Aryl) Conjugate Ligands for Asymmetric Transfer Hydrogenation of Aryl Ketones
  作者：Andrea Kišić、Michel Stephan、Barbara Mohar

  DOI：10.1002/adsc.201500288

  日期：2015.8.10

  New 3rd generation designer ansa‐ruthenium(II) complexes featuring N,C‐alkylene‐tethered N,N‐dialkylsulfamoyl‐DPEN/η6‐arene ligands, exhibited good catalytic performance in the asymmetric transfer hydrogenation (ATH) of various classes of (het)aryl ketones in formic acid/triethylamine mixture. In particular, benzo‐fused cyclic ketones furnished 98 to >99.9% ee using a low catalyst loading.

  新3次代设计师柄-钌（II）络合物配Ñ，Ç -亚烷基-拴系的Ñ，Ñ -dialkylsulfamoyl-DPEN /η 6个-arene配体，在各种类的不对称转移氢化（ATH）显示出良好的催化性能甲酸/三乙胺混合物中的（杂）芳基酮。特别是，在低催化剂负载下，苯并稠合的环状酮可提供98至99.9％ee的ee。
• Oxidation of Sulfur-Containing Compounds with HOF·CH₃CN
  作者：Shlomo Rozen、Yifat Bareket

  DOI：10.1021/jo961862e

  日期：1997.3.1

  The HOF . CH3CN complex, easily prepared by passing F-2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. All types of sulfides have been oxidized to sulfones in excellent yields, in a few minutes at room temperature. The reaction proceeds through the formation of sulfoxides which at low temperatures of around -75 degrees C could be isolated in good yields. It was demonstrated through a reaction with thianthrene 5-oxide (20) that HOF . CH3CN is strongly electrophilic in nature. Sulfides with an electron-depleted sulfur atom such as perfluoroalkyl or aryl sulfides, which could not be well oxidized by any other method, were also efficiently converted to the corresponding sulfones in minutes. Thiophenes are generally hard to oxidize to the corresponding S-dioxides since the conditions required by the orthodox oxidants encourage consecutive typical ene and diene reactions. HOF . CH3CN requires;short reaction times and low temperatures, thus enabling the isolation of thiophene dioxides, some of which could not be made by any other way. It seems that apart from unprotected amines, other functional groups such as aromatic rings, ketones, hydroxyls, and ethers do not interfere, since the sulfur atom reacts considerably faster.
• Binuclear manganese complexes as catalysts in the selective and efficient oxidation of sulfides to sulfones
  作者：Derek H.R. Barton、Wenge Li、Jason A. Smith

  DOI：10.1016/s0040-4039(98)01518-4

  日期：1998.9

  The binuclear MnIVMnIV manganese complex 1 catalyzes the periodic acid oxidation of sulfides to sulfones under mild conditions. The reaction was found to be highly selective giving almost quantitative yields of the sulfones even in the presence other easily oxidized groups. Only amines were found to hinder the reaction.

  在温和条件下，双核Mn IV complexMn IV锰络合物1催化硫化物的高碘酸氧化为砜。发现该反应是高度选择性的，即使在存在其他易于氧化的基团的情况下，也给出了几乎定量的砜收率。仅发现胺会阻碍反应。
• Enzymatic resolution of chroman-4-ol and its core analogues with Burkholderia cepacia lipase
  作者：Olexandr V. Kucher、Anastasiya O. Kolodyazhnaya、Oleg B. Smolii、Alexandr I. Boiko、Vladimir S. Kubyshkin、Pavel K. Mykhailiuk、Andrey A. Tolmachev

  DOI：10.1016/j.tetasy.2014.02.010

  日期：2014.4

  A convenient protocol for lipase resolution of chroman-4-ol and its analogues (six- and seven-membered rings with O, S, SO2) has been elaborated. The structure of substrates has minor influence on the efficiency of resolution. (C) 2014 Elsevier Ltd. All rights reserved.