4-tert-butyl-5-(2-hydroxy-1,1'-binaphthyl-5-yl)-3,3-dimethyl-2,3-dihydrofuran | 918830-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-tert-butyl-5-(2-hydroxy-1,1'-binaphthyl-5-yl)-3,3-dimethyl-2,3-dihydrofuran
• 英文别名: 5-(4-tert-butyl-3,3-dimethyl-2H-furan-5-yl)-1-naphthalen-1-ylnaphthalen-2-ol
• CAS: 918830-05-4
• 化学式: C₃₀H₃₀O₂
• 分子量: 422.567
• InChiKey: BZEWAOVSLONRMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-5-(2-hydroxy-1,1'-binaphthyl-5-yl)-3,3-dimethyl-2,3-dihydrofuran 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-tert-butyl-1-(2-hydroxy-1,1'-binaphthyl-5-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane 、 5-tert-butyl-1-(2-hydroxy-1,1'-binaphthyl-5-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
  参考文献：
  名称：

  Synthesis of bicyclic dioxetanes bearing a 2-hydroxy-1,1′-binaphthyl-5-yl moiety active toward intramolecular charge-transfer-induced chemiluminescent decomposition

  摘要：

  Five pairs of diastereoisomeric dioxetanes, cis- and trans-2a-2e, were synthesized. These dioxetanes underwent intramolecular charge-transfer-induced decomposition with accompanying emission of orange light in TBAF in DMSO (system A) as a complete homoge of neous system and in [K subset of (18C6)](+)t-BuO- in PhH-THF (system B) as a sterically anisotropic environment. Maximum wavelength (lambda(CTICL)(max)) chemiluminescence did not vary practically with the triggering system. The lambda(CTICL)(max) was little affected also by substituents on the upper-Nap of dioxetanes 2, nor by the difference in their stereochemistry, namely, cis- or trans-isomer. On the other hand, chemiluminescent efficiency was found to split up depending on stereochemistry of 2. Dioxetane 2b bearing a methoxycarbonyl group on the upper-Nap gave significantly weak light, while its free carboxylic acid analog 2c afforded light effectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.108
• 作为产物：
  描述：

  1-萘基溴化镁, 0.5M IN METHF 在 四(三苯基膦)钯 sodium thiomethoxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 4-tert-butyl-5-(2-hydroxy-1,1'-binaphthyl-5-yl)-3,3-dimethyl-2,3-dihydrofuran
  参考文献：
  名称：

  Synthesis of bicyclic dioxetanes bearing a 2-hydroxy-1,1′-binaphthyl-5-yl moiety active toward intramolecular charge-transfer-induced chemiluminescent decomposition

  摘要：

  Five pairs of diastereoisomeric dioxetanes, cis- and trans-2a-2e, were synthesized. These dioxetanes underwent intramolecular charge-transfer-induced decomposition with accompanying emission of orange light in TBAF in DMSO (system A) as a complete homoge of neous system and in [K subset of (18C6)](+)t-BuO- in PhH-THF (system B) as a sterically anisotropic environment. Maximum wavelength (lambda(CTICL)(max)) chemiluminescence did not vary practically with the triggering system. The lambda(CTICL)(max) was little affected also by substituents on the upper-Nap of dioxetanes 2, nor by the difference in their stereochemistry, namely, cis- or trans-isomer. On the other hand, chemiluminescent efficiency was found to split up depending on stereochemistry of 2. Dioxetane 2b bearing a methoxycarbonyl group on the upper-Nap gave significantly weak light, while its free carboxylic acid analog 2c afforded light effectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.108

文献信息

• Synthesis of bicyclic dioxetanes bearing a 2-hydroxy-1,1′-binaphthyl-5-yl moiety active toward intramolecular charge-transfer-induced chemiluminescent decomposition
  作者：Naoyuki Hoshiya、Nobuko Watanabe、Hisako K. Ijuin、Masakatsu Matsumoto

  DOI：10.1016/j.tet.2006.09.108

  日期：2006.12

  Five pairs of diastereoisomeric dioxetanes, cis- and trans-2a-2e, were synthesized. These dioxetanes underwent intramolecular charge-transfer-induced decomposition with accompanying emission of orange light in TBAF in DMSO (system A) as a complete homoge of neous system and in [K subset of (18C6)](+)t-BuO- in PhH-THF (system B) as a sterically anisotropic environment. Maximum wavelength (lambda(CTICL)(max)) chemiluminescence did not vary practically with the triggering system. The lambda(CTICL)(max) was little affected also by substituents on the upper-Nap of dioxetanes 2, nor by the difference in their stereochemistry, namely, cis- or trans-isomer. On the other hand, chemiluminescent efficiency was found to split up depending on stereochemistry of 2. Dioxetane 2b bearing a methoxycarbonyl group on the upper-Nap gave significantly weak light, while its free carboxylic acid analog 2c afforded light effectively. (c) 2006 Elsevier Ltd. All rights reserved.