5-溴-6-酚羟基色满 | 32337-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 5-溴-6-酚羟基色满
• 英文名称: 5-bromo-6-chromanol
• 英文别名: 5-bromo-chroman-6-ol；5-Bromo-6-chromanol；5-bromo-3,4-dihydro-2H-chromen-6-ol
• CAS: 32337-88-5
• 化学式: C₉H₉BrO₂
• 分子量: 229.073
• InChiKey: SOQLKPVPDJGAOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-6-酚羟基色满 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以21%的产率得到6-羟基色满
  参考文献：
  名称：

  Synthesis of spirodienone derivatives and their conversion into dihydrobenzopyrans

  摘要：

  The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00479-3
• 作为产物：
  描述：

  6-溴苯并二氢吡喃 在 碘 、 tetra-N-butylammonium tribromide 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 5-溴-6-酚羟基色满
  参考文献：
  名称：

  Regenerable Radical-Trapping Tellurobistocopherol Antioxidants

  摘要：

  Tellurobistocopherols 9-11 were prepared by lithiation of the corresponding bromotocopherols, reaction with tellurium tetrachloride and reductive workup. Compounds 9-11 quenched linoleic-acid-derived peroxyl radicals much more efficiently than alpha-tocopherol in a chlorobenzene/water two-phase system. N-Acetylcysteine or tris(2-carboxylethyl)phosphine as co-antioxidants in the aqueous phase could regenerate the tellurobistocopherols and increase their inhibition times. Antioxidant 11 inhibited peroxidation for 7-fold longer than that recorded with alpha-tocopherol. Thiol consumption in the aqueous phase was monitored and found to be inversely related to the inhibition time.

  DOI：

  10.1021/acs.joc.6b02450

文献信息

• 10.1021/jacs.4c04608
  作者：Kim, Raphael S.、Kgoadi, Lebogang O.、Hayes, Jacob C.、Rainboth, Derek P.、Mudd, Catherine M.、Yap, Glenn P. A.、Watson, Donald A.

  DOI：10.1021/jacs.4c04608

  日期：——

  We report a highly cross- and atroposelective coupling between ortho-(chloro)arylphosphine oxides and ortho-(bromo)aryl ethers. This previously unknown asymmetric nickel-catalyzed reaction offers a direct route to highly enantioenriched axially chiral biaryl monophosphine oxides that are difficult to access by other means. These products can be readily reduced to generate chiral MOP-type ligands bearing

  我们报道了邻（氯）芳基氧化膦和邻（溴）芳基醚之间的高度交叉和间质选择性偶联。这种以前未知的不对称镍催化反应为高度对映体富集的轴向手性联芳基单膦氧化物提供了直接途径，而这是通过其他方法难以获得的。这些产物可以很容易地还原生成带有复杂骨架的手性 MOP 型配体。还证明了这些手性配体在不对称催化中的效用。
• Synthesis of spirodienone derivatives and their conversion into dihydrobenzopyrans
  作者：Kazuki Mori、Shosuke Yamamura、Shigeru Nishiyama

  DOI：10.1016/s0040-4020(01)00479-3

  日期：2001.6

  The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Regenerable Radical-Trapping Tellurobistocopherol Antioxidants
  作者：Jia-fei Poon、Jiajie Yan、Vijay P. Singh、Paul J. Gates、Lars Engman

  DOI：10.1021/acs.joc.6b02450

  日期：2016.12.16

  Tellurobistocopherols 9-11 were prepared by lithiation of the corresponding bromotocopherols, reaction with tellurium tetrachloride and reductive workup. Compounds 9-11 quenched linoleic-acid-derived peroxyl radicals much more efficiently than alpha-tocopherol in a chlorobenzene/water two-phase system. N-Acetylcysteine or tris(2-carboxylethyl)phosphine as co-antioxidants in the aqueous phase could regenerate the tellurobistocopherols and increase their inhibition times. Antioxidant 11 inhibited peroxidation for 7-fold longer than that recorded with alpha-tocopherol. Thiol consumption in the aqueous phase was monitored and found to be inversely related to the inhibition time.