rac-(2R,3R)-3-(7-ethoxycarbonyl-1,1-dimethyl-3-oxaheptyl)-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rac-(2R,3R)-3-(7-ethoxycarbonyl-1,1-dimethyl-3-oxaheptyl)-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran
• 英文别名: ethyl 5-[2-[(2S,3S)-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyloxolan-3-yl]-2-methylpropoxy]pentanoate
• 化学式: C₂₄H₃₈O₆
• 分子量: 422.562
• InChiKey: YESDSJOZPKEPGC-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2,4,4-tetramethyl-3-oxopentanedioic acid dimethyl ester 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 水 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.5h， 生成 rac-(2S,3R)-3-(7-ethoxycarbonyl-1,1-dimethyl-3-oxaheptyl)-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran 、 rac-(2R,3R)-3-(7-ethoxycarbonyl-1,1-dimethyl-3-oxaheptyl)-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran
  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

• Synthesis of bicyclic dioxetanes tethering a fluororescer through an ω-carbamoyl-substituted linker and their high-performance chemiluminescence in an aqueous system
  作者：Nobuko Watanabe、Hidetoshi Kino、Shinichiro Watanabe、Hisako K. Ijuin、Masashi Yamada、Masakatsu Matsumoto

  DOI：10.1016/j.tet.2012.04.078

  日期：2012.7

  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.