4-tert-butyl-5-[2'-hydroxy-3'-methoxycarbonyl-2-(4-methylphenylsulfonyloxy)-1,1'-binaphthyl-5-yl]-3,3-dimethyl-2,3-dihydrofuran | 918829-96-6

• 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-3'-methoxycarbonyl-2-(4-methylphenylsulfonyloxy)-1,1'-binaphthyl-5-yl]-3,3-dimethyl-2,3-dihydrofuran
• CAS: 918829-96-6
• 化学式: C₃₉H₃₈O₇S
• 分子量: 650.793
• InChiKey: XOPMDLVLAUTUFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.04
• 重原子数：
  47.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-5-[2'-hydroxy-3'-methoxycarbonyl-2-(4-methylphenylsulfonyloxy)-1,1'-binaphthyl-5-yl]-3,3-dimethyl-2,3-dihydrofuran 在 sodium hydroxide 、 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 4-tert-butyl-5-(2-hydroxy-2'-methoxy-3'-methoxycarbonyl-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
• 作为产物：
  描述：

  5'-(4-t-butyl-3,3-dimethyl-2,3-dihydrofuran-5-yl)-2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylic acid methyl ester 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以75.1%的产率得到4-tert-butyl-5-[2'-hydroxy-3'-methoxycarbonyl-2-(4-methylphenylsulfonyloxy)-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