5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran N-hydroxysuccinimide ester | 594859-93-5

• 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: 5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran N-hydroxysuccinimide ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 5-[2-[5-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]-3,3-dimethyl-2H-furan-4-yl]-2-methylpropoxy]pentanoate
• CAS: 594859-93-5
• 化学式: C₃₁H₄₇NO₇Si
• 分子量: 573.802
• InChiKey: QSAABHQPJRPTNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  611.5±65.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran N-hydroxysuccinimide ester 在 氧气 、 tetraphenylporphyrin 、 三乙胺 、 sodium thiomethoxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 N-(4-(benzo[d]thiazol-2-yl)-3-hydroxybenzyl)-5-(2-(1-(3-hydroxyphenyl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptan-5-yl)-2-methylpropoxy)pentanamide
  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：

  4-(7-carboxy-1,1-dimethyl-3-oxaheptyl )-5-(3-hydroxyphenyl)-3,3-dimethyl-2,3-dihydrofuran 在 咪唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran N-hydroxysuccinimide ester
  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.