4-[2-(3-methoxybenzyloxy)-1,1-dimethylethyl]-2,2,5,5-tetramethyl-1,3-dioxane | 594859-72-0

• 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: 4-[2-(3-methoxybenzyloxy)-1,1-dimethylethyl]-2,2,5,5-tetramethyl-1,3-dioxane
• 英文别名: 4-[1-[(3-Methoxyphenyl)methoxy]-2-methylpropan-2-yl]-2,2,5,5-tetramethyl-1,3-dioxane
• CAS: 594859-72-0
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: IWUXATDCAXNYHL-UHFFFAOYSA-N

物化性质

• 沸点：
  398.0±27.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[2-(3-methoxybenzyloxy)-1,1-dimethylethyl]-2,2,5,5-tetramethyl-1,3-dioxane 在 盐酸 、 水 、 4-甲基苯磺酸吡啶 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-5-(tetrahydro-2H-pyran-2-yloxy)-pentan-3-ol
  参考文献：
  名称：

  Synthesis of bicyclic dioxetanes tethering a fluororescer through an ω-carbamoyl-substituted linker and their high-performance chemiluminescence in an aqueous system

  摘要：

  Bicyclic dioxetanes 3 and 4 tethering a fluorescein or 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety through a linker were synthesized by the use of dihydrofuran-intermediate 5 or its advanced intermediate 6. These dioxetanes underwent base-induced decomposition to effectively give light due to intramolecular energy-transfer from an excited oxidobenzoate to a tethered fluorophore. Although the chemiluminescence efficiency Phi(CL) values for 3 and 4 were only ca. 2-fold greater than that for parent 2 in a TBAF/acetonitrile system, these values were 30-550-fold greater than that for 2 in a NaOH/H2O system. Such marked increase of Phi(CL) was hardly observed by the simple addition of 25 or 26 as a model of a tethered fluorescer. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.078
• 作为产物：
  描述：

  2,2,4,4-tetramethyl-3-oxopentanedioic acid dimethyl ester 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.0h， 生成 4-[2-(3-methoxybenzyloxy)-1,1-dimethylethyl]-2,2,5,5-tetramethyl-1,3-dioxane
  参考文献：
  名称：

  Synthesis of bicyclic dioxetanes tethering a fluororescer through an ω-carbamoyl-substituted linker and their high-performance chemiluminescence in an aqueous system

  摘要：

  Bicyclic dioxetanes 3 and 4 tethering a fluorescein or 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety through a linker were synthesized by the use of dihydrofuran-intermediate 5 or its advanced intermediate 6. These dioxetanes underwent base-induced decomposition to effectively give light due to intramolecular energy-transfer from an excited oxidobenzoate to a tethered fluorophore. Although the chemiluminescence efficiency Phi(CL) values for 3 and 4 were only ca. 2-fold greater than that for parent 2 in a TBAF/acetonitrile system, these values were 30-550-fold greater than that for 2 in a NaOH/H2O system. Such marked increase of Phi(CL) was hardly observed by the simple addition of 25 or 26 as a model of a tethered fluorescer. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.078

文献信息

• 1,2-DIOXETANE DERIVATES AND REAGENTS EMPLOYING THEM
  申请人：TOSOH CORPORATION

  公开号：EP1342724B1

  公开（公告）日：2016-01-06