4-tert-butyl-5-(2-formyl-5-methoxyphenyl)-3,3-dimethyl-2,3-dihydrofuran | 1374343-29-9

• 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-tert-butyl-5-(2-formyl-5-methoxyphenyl)-3,3-dimethyl-2,3-dihydrofuran
• CAS: 1374343-29-9
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: HXGKTGSSYBGSPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-5-(2-formyl-5-methoxyphenyl)-3,3-dimethyl-2,3-dihydrofuran 在 偶氮二异丁腈 、 potassium tert-butylate 、 三正丁基氢锡 、 sodium thiomethoxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of Bicyclic Dioxetanes Bearing a Hydroxyphenanthrene or Hydroxy[4]helicene Moiety and Their Base-Induced Chemiluminescent Decomposition

  摘要：

  Six bicyclic dioxetanes bearing a 1-hydroxyphenanthren-3-yl 2-iv, 3-hydroxyphenanthren-1-yl 2-ov, 4-hydroxyphenanthren-2-yl 2-oh, 2-hydroxyphenanthren-4-yl 2-ih, 4-hydroxy[4]helicen-2-yl 3-iv and 2-hydroxy[4]helicen-4-yl group 3-ov were synthesized and their base-induced chemiluminescent decomposition was investigated in a TBAF (tetrabutylammonium fluoride) / MeCN system. For dioxetanes in the iv-series 2-iv and 3-iv including alpha-naphthol-analog 17a and those in the ov-series 2-ov and 3-ov including beta-naphthol-analog 17b, we investigated how the chemiluminescence properties changed with an increase in the number of fused benzene rings of a hydroxyarene moiety attached to a dioxetane ring. The results showed that a) maximum wavelength of chemiluminescence lambda(CL)(max) tended to shift to a longer wavelength region as the number of fused benzene rings increased, b) the k(CTID) values for the iv-series were >1000 times larger than those for the ov-series regardless of the number of fused benzene rings, and c) a dioxetane in the iv-series tended to have a higher singlet-chemiexcitation efficiency Phi(S) than the corresponding dioxetane in the ov-series. This tendency could be explained by the "syn/anti" rotational isomerism of an aromatic electron donor, where an anti-rotamer gives Phi(S) far more effectively than a syn-rotamer.

  DOI：

  10.3987/com-14-s(k)43

文献信息

• Base-Induced Chemiluminescent Decomposition of Bicyclic Dioxetanes Bearing a (Benzothiazol-2-yl)-3-hydroxyphenyl Group: A Radiationless Pathway Leading to Marked Decline of Chemiluminescence Efficiency
  作者：Masatoshi, Tanimura、Nobuko Watanabe、Hisako K. Ijuin、Masakatsu Matsumoto

  DOI：10.1021/jo300417e

  日期：2012.5.18

  Charge-transfer-induced decomposition (CTID) of bicyclic dioxetanes 1b–d bearing a 3-hydroxylphenyl moiety substituted with a benzothiazol-2-yl group at the 2-, 6-, or 5-position was investigated, and their chemiluminescence properties were compared to each other, based on those for a 4-benzothiazolyl analogue 1a. Dioxetanes 1c and 1d underwent CTID to give the corresponding oxido anions of keto esters

  研究了在2-，6-或5-位上带有被苯并噻唑-2-基取代的3-羟基苯基部分的双环二氧杂环丁烷1b - d的电荷转移诱导分解（CTID），其化学发光性质为根据4-苯并噻唑基类似物1a的结果进行比较。与1a的情况类似，对二氧环乙烷1c和1d进行CTID生成单线激发态的酮酸酯8c或8d的相应氧化阴离子。另一方面，尽管1b仅产生酮酸酯，但其化学发光效率很低。2b。1b化学发光效率的显着下降归因于1b主要通过无辐射途径分解为8b，其中苯并噻唑基中氮的分子内亲核攻击二氧杂环丁烷O-O产生环状中间体cis - 11。