5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran | 594859-92-4

• 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
• 英文别名: 4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-5-(3-t-butyldimethylsiloxyphenyl)-3,3-dimethyl-2,3-dihydrofuran；5-[2-[5-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]-3,3-dimethyl-2H-furan-4-yl]-2-methylpropoxy]pentanoic acid
• CAS: 594859-92-4
• 化学式: C₂₇H₄₄O₅Si
• 分子量: 476.729
• InChiKey: VDSLJZCQALKSBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

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 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 C₂₇H₄₃ClO₄Si
  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-ethoxycarbonyl-1,1-dimethyl-3-oxaheptyl)-5-(3-methoxyphenyl)-3,3-dimethyl-2,3-dihydrofuran 在 咪唑 、 sodium thiomethoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran
  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 derivatives and reagents employing them
  申请人：TOSOH CORPORATION

  公开号：US20030207329A1

  公开（公告）日：2003-11-06

  A 1,2-dioxetane derivative of the formula (I): 1 wherein Ar is an aryl group which may have an alkyl group, an aryl group, a halogen atom, an alkoxyl group, a carboxyl group, a formyl group, an alkyl ester, an aryl ester, an alkylketone, an arylketone or a hetero ring bonded thereto, X is a substituent capable of labeling an organic compound or a biological molecule, or an ester, Y is a hydrogen atom, an acyl group or a group of the formula —Si(R 4 R 5 R 6 ) (wherein each of R 4 , R 5 and R 6 which are independent of one another, is an alkyl group or an aryl group), Z is an alkyl group, an aryl group, an oxygen atom, a sulfur atom, a carbonyl group, —(CO)—O—, —O—(CO)—, —NH—, —NH—CO—, —CO—NH—, —OSi(R 7 R 8 )— (wherein each of R 7 and R 8 which are independent of each other, is an alkyl group or aryl group) or a group of the formula —(R 9 R 10 )SiO— (wherein each of R 9 and R 10 which are independent of each other, is an alkyl group or an aryl group), each of R 1 and R 2 is an alkyl group or an aryl group, and R 3 is a spacer.

  Ar是一个可能带有烷基，芳香基，卤素原子，烷氧基，羧基，甲酰基，烷基酯，芳基酯，烷基酮，芳基酮或异环与之结合的芳基，X是能够标记有机化合物或生物分子的取代基，或酯，Y是氢原子，酰基或式—Si(R4R5R6)的基团（其中R4、R5和R6各自独立，是烷基或芳基），Z是烷基，芳基，氧原子，硫原子，羰基，—(CO)—O—，—O—(CO)—，—NH—，—NH—CO—，—CO—NH—，—OSi(R7R8)—（其中R7和R8各自独立，是烷基或芳基）或式—(R9R10)SiO—（其中R9和R10各自独立，是烷基或芳基），R1和R2各自是烷基或芳基，R3是一个间隔物。
• 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.