1-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)ethan-1-ol | 926907-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)ethan-1-ol
• CAS: 926907-29-1
• 化学式: C₁₆H₂₈O₄Si
• 分子量: 312.481
• InChiKey: CFBJWPBTLCILBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)ethan-1-ol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 2,6-Dimethoxy-4-(2-methyl-1,3-dioxolan-2-yl)phenol
  参考文献：
  名称：

  Total synthesis of (±)-nitidanin and novel procedures for determination of the location of the side chains on 1,4-benzodioxane

  摘要：

  Regioselective cycloaddition of o-quinone 4 and protected sinapyl alcohol 2 gave 1,4-benzodioxane 5, which was converted to (+/-)-nitidanin (6), an antimalarial compound. Two novel procedures were developed to determine the location of the side chains of the adduct (5) based on partial ring cleavage. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.170
• 作为产物：
  描述：

  丁香醛 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)ethan-1-ol
  参考文献：
  名称：

  Total synthesis of (±)-nitidanin and novel procedures for determination of the location of the side chains on 1,4-benzodioxane

  摘要：

  Regioselective cycloaddition of o-quinone 4 and protected sinapyl alcohol 2 gave 1,4-benzodioxane 5, which was converted to (+/-)-nitidanin (6), an antimalarial compound. Two novel procedures were developed to determine the location of the side chains of the adduct (5) based on partial ring cleavage. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.170

文献信息

• Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins
  作者：Biao Yang、Kui Dong、Xiang-Sheng Li、Li-Zhu Wu、Qiang Liu

  DOI：10.1021/acs.orglett.2c00566

  日期：2022.3.18

  photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water

  通过含有催化质子化部花青 (MEH) 的亚稳态光酸体系，开发了一种环境友好且高度非对映选择性合成茚满的方法。在可见光照射下，MEH 产生亚稳态螺结构并释放质子，这有助于从苯甲醇中形成碳正离子，从而在各种亲核试剂存在下传递多种分子。主要是从苯甲醇和烯烃中很容易得到多种茚满烷，而水是唯一的副产物。
• Inverse electron demand hetero-Diels–Alder reaction in preparing 1,4-benzodioxin from o-quinone and enamine
  作者：Jinsong Zhang、Chris Taylor、Erich Bowman、Leo Savage-Low、Michael W. Lodewyk、Larry Hanne、Guang Wu

  DOI：10.1016/j.tetlet.2013.09.013

  日期：2013.11

  A process for synthesizing 1,4-benzodioxin, through oxidation of a phenol to an o-quinone followed by treatment with an enamine, has been developed. Adduct stereochemistry is found to be retained via this one-pot reaction. The method uses hypervalent iodine reagent under mild conditions and is compatible with a wide scope of phenols and enamines. Published by Elsevier Ltd.