5-(4-bromo-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-bromo-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran
• 英文别名: 5-(4-bromo-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2H-furan
• 化学式: C₁₇H₂₃BrO₂
• 分子量: 339.272
• InChiKey: QVFZNZSWXBBWAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-bromo-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran 在 正丁基锂 、 三氟甲磺酸酐 、 三苯基氧化膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-tert-butyl-5-[3-methoxy-4-(N-phenylbenzimidazol-2-yl)phenyl]-3,3-dimethyl-2,3-dihydrofuran
  参考文献：
  名称：

  Synthesis of Bicyclic Dioxetanes Bearing a 4-(Benzimidazol-2-yl)-3-hydroxyphenyl Group and Their Base-Induced Chemiluminescent Decomposition in an Aprotic Medium and in an Aqueous Medium

  摘要：

  Bicyclic dioxetane, 5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane, bearing a 4-(benzimidazol-2-yl)-3-hydroxyphenyl group at the 1-position and its N-substituted benzimidazolyl-analogs were synthesized. N-Methylbenzimidazolyl-analog and N-phenylbenzimidazolyl-analog were found to undergo charge-transfer-induced decomposition (CTID) to effectively give light in both TBAF/MeCN and in NaOH/H2O. The CTID of N-(4-carboxybutyl)benzimidazolyl-analog gave also effectively light both in MeCN and in H2O. On the other hand, chemiluminescent CTID of the unsubstituted benzimidazolyl-analog changed depending on the base used: TBAF/MeCN induced weak emission of yellow light due to a dianion of the dioxetane, while TMG(tetramethylguanidine)/MeCN induced strong emission of blue light due to a monoanion of the dioxetane.

  DOI：

  10.3987/com-12-12602
• 作为产物：
  描述：

  2-(4-bromo-3-methoxyphenyl)-3-t-butyl-3-hydroxy-4,4-dimethyl-2,3,4,5-tetrahydrofuran 在 sodium chloride 、 对甲苯磺酸一水合物 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 以85%的产率得到5-(4-bromo-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran
  参考文献：
  名称：

  1,2-dioxetane derivates, luminescent reagents, luminescence methods and measuring methods

  摘要：

  公开号：

  EP1238976B1

文献信息

• Highly effective and rapid emission of light from bicyclic dioxetanes bearing a 3-hydroxyphenyl substituted with a 4-p-oligophenylene moiety in an aqueous system: Two different ways for the enhancement of chemiluminescence efficiency
  作者：Nobuko Watanabe、Hikaru Takatsuka、Hisako K. Ijuin、Masakatsu Matsumoto

  DOI：10.1016/j.tet.2020.131203

  日期：2020.6

  Base-induced decomposition (BID) of bicyclic dioxetanes bearing a 3-hydroxyphenyl substituted with 4-p-oligophenylene moiety proceeded rapidly to give bright light even in water as well as in acetonitrile or DMSO. Addition of β-MCD (methylated β-cyclodextrin) or TBHP (tributylhexadecylphosphonium bromide) to an aqueous system improved chemiluminescence efficiency of these dioxetanes. However, β-MCD

  带有3-对羟基苯并被4-对-低聚亚苯基部分取代的双环二氧杂环丁烷的碱诱导分解（BID）迅速进行，即使在水以及乙腈或DMSO中也能发出明亮的光。将β-MCD（甲基化的β-环糊精）或TBHP（三丁基十六烷基溴化phosph）添加到水性体系中可改善这些二氧杂环丁烷的化学发光效率。然而，β-MCD在不降低BID发生率的情况下起作用，而TBHP大大降低了发生率。
• 1,2-Dioxetane derivatives, luminescent reagents, luminescence methods and measuring methods
  申请人：TOSOH CORPORATION

  公开号：US20020132365A1

  公开（公告）日：2002-09-19

  A 1,2-dioxetane derivative of the formula (I): 1 wherein each of R 1 and R 2 which are independent of each other, is a hydrogen atom, an alkyl group or an aryl group, or R 1 and R 2 may together form a cyclic or polycyclic organic ring group spiro-bonded to the dioxetane ring, R 3 is an alkyl group or an aryl group, or R 3 and R 1 or R 2 may together form a condensed ring containing the dioxetane ring and a hetero atom, and Ar is a group of the formula (A): 2 wherein R 4 is a hydroxyl group , an alkoxyl group, an aralkyloxy group, a group of —OSi(R 5 R 6 R 7 ) (wherein each of R 5 , R 6 and R 7 which are independent of one another, is an alkyl group alky; group or and aryl group), a phosphate group or a group of —S(C═O)R 8 (wherein R 8 is an alkyl group or an aryl group), each of R 9 and R 10 which are independent of each other, is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, X is a halogen atom, and V is an oxygen atom or a sulfur atom, or a group of the formula (B): 3 wherein R 4 is the same as R in the above formula (A), each of R 11 and R 12 which are independent of each other, is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, Y is a halogen atom, and W is an oxygen atom or a sulfur atom.

  公式（I）的1,2-二氧杂环戊烷衍生物，其中R1和R2各自独立地是氢原子、烷基或芳基，或者R1和R2可以共同形成一个环状或多环有机环基，与二氧杂环戊烷环螺合，R3是烷基或芳基，或者R3和R1或R2可以共同形成一个含有二氧杂环戊烷环和杂原子的缩合环，Ar是公式（A）的基团：其中R4是羟基、烷氧基、芳基烷氧基、—OSi（R5R6R7）（其中R5、R6和R7各自独立地是烷基、烷基或芳基），磷酸酯基或—S（C═O）R8（其中R8是烷基或芳基），R9和R10各自独立地是氢原子、烷基、芳基或卤素原子，X是卤素原子，V是氧原子或硫原子，或者公式（B）的基团：其中R4与上述公式（A）中的R相同，R11和R12各自独立地是氢原子、烷基、芳基或卤素原子，Y是卤素原子，W是氧原子或硫原子。
• Hydrogen bonding network-assisted chemiluminescent thermal decomposition of 3-hydroxyphenyl-substituted dioxetanes in crystal
  作者：Nobuko Watanabe、Hikaru Takatsuka、Hisako K. Ijuin、Ayu Wakatsuki、Masakatsu Matsumoto

  DOI：10.1016/j.tetlet.2016.05.004

  日期：2016.6

  thermal decomposition in solution (TDsoln) to form 3-oxopentyl 3-hydroxybenzoate 4 accompanied by the emission of light [λmaxCL (TDsoln) = 405 nm] due to an excited 3-oxopentyl group in 4. Dioxetane 1 also exclusively gave 4 by thermal decomposition in crystal (TDcryst). However, in contrast to TDsoln, TDcryst of 1 gave light [λmaxCL (TDcryst) = 464 nm] due to excited oxidobenzoate 3∗ and/or its closely

  双环二恶丁环1轴承3-羟基苯基组中的溶液（TD进行热分解SOLN），以形成3-氧代戊基-3-羟基苯4伴随的发光[ λ最大CL（TD SOLN）= 405 nm]的由于激发3 -氧戊基4。二氧杂环丁烷1还通过晶体热分解（TD cryST）专门得到4。然而，在对比TD SOLN，TD CRYST的1得到的光[ λ最大CL（TD CRYST）= 464 nm]是由于受激发的氧化苯甲酸酯3 ∗和/或由CTID（电荷转移诱导分解）机制形成的紧密相关的物种。独特的化学发光TD cryST为1大概是由于在二氧杂环丁烷分子的酚质子和另一个二氧杂环丁烷分子的过氧化物氧之间的晶体中形成了氢键的结果。在这项工作中，还研究了带有4-芴基-3-羟苯基部分10的双环二氧杂环丁烷类似物和带有3-羟苯基5b的金刚烷-二氧杂环丁烷的TD晶体和TD溶胶。
• 1,2-dioxetane derivative
  申请人：FUJIREBIO INC.

  公开号：EP0943618A2

  公开（公告）日：1999-09-22

  The present invention has its objects to provide a compound not only which is easy to handle, thermally stable, and high in emission efficiency, but also which can show high emission efficiency without coexisting enhancer in the system even in a protic solvent. The present invention is related to a 1,2-dioxetane derivative of general formula (I). [wherein R1, R2, R3, R4 and R5 each independently represents hydrogen, alkyl or aryl; a pair of R2 and R3 and a pair of R4 and R5 may respectively be joined to each other to form a cycloalkyl group.

  本发明的目的是提供一种不仅易于处理、热稳定性好、发射效率高，而且即使在质子溶剂中也能在体系中不共存增强剂的情况下显示出高发射效率的化合物。 本发明涉及通式（I）的 1，2-二氧杂环丁烷衍生物。 [其中 R1、R2、R3、R4 和 R5 各自独立地代表氢、烷基或芳基；一对 R2 和 R3 以及一对 R4 和 R5 可分别相互连接形成环烷基。
• US6218135B1
  申请人：——

  公开号：US6218135B1

  公开（公告）日：2001-04-17