5-tert-butyl-1-(4-cyanomethyl)phenyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane | 526198-09-4

• 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-tert-butyl-1-(4-cyanomethyl)phenyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
• 英文别名: 2-[4-(5-Tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptan-1-yl)phenyl]acetonitrile；2-[4-(5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptan-1-yl)phenyl]acetonitrile
• CAS: 526198-09-4
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: MGGWKRBRSOPBME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-1-(4-cyanomethyl)phenyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane 以 对二甲苯 为溶剂， 反应 2.0h， 生成 4-(cyanomethyl)benzoic acid 2,2,4,4-tetramethyl-3-oxopentyl ester
  参考文献：
  名称：

  Intramolecular charge-transfer-induced chemiluminescent decomposition of 1,2-dioxetanes bearing a phenylmethanide anion

  摘要：

  Dioxetanes (1) bearing a phenyl moiety substituted with a methylene or methine having an electron-withdrawing group(s) (-CH2-Ew or -CH(X)-Ew) and dioxetane (2) bearing a 3-(1-cyanoethenyl)phenyl group were synthesized. Treatment of dioxetanes (1) with tetrabutylammonium fluoride (TBAF) caused their decomposition with accompanying emission of light with maximum wavelength at 530-758 nm. The Michael addition of a bis(methoxycarbonyl)methanide anion to dioxetane (2) produced initially ail unstable dioxetane bearing a phenylmethanide anion, decomposition of which gave light with maximum wavelength at 710-740 nm. Intramolecular cyclopropanation without decomposition of the dioxetane ring took place concurrently for the Michael reaction-induced decomposition of 2 with the bis(methoxycarbonyl)chloromethanide anion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.081
• 作为产物：
  描述：

  4-tert-butyl-5-[4-(bromomethyl)phenyl]-3,3-dimethyl-2,3-dihydrofuran 在 氧气 、 四丁基硫酸氢铵 、 tetraphenylporphyrin 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 5-tert-butyl-1-(4-cyanomethyl)phenyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
  参考文献：
  名称：

  Intramolecular charge-transfer-induced chemiluminescent decomposition of 1,2-dioxetanes bearing a phenylmethanide anion

  摘要：

  Dioxetanes (1) bearing a phenyl moiety substituted with a methylene or methine having an electron-withdrawing group(s) (-CH2-Ew or -CH(X)-Ew) and dioxetane (2) bearing a 3-(1-cyanoethenyl)phenyl group were synthesized. Treatment of dioxetanes (1) with tetrabutylammonium fluoride (TBAF) caused their decomposition with accompanying emission of light with maximum wavelength at 530-758 nm. The Michael addition of a bis(methoxycarbonyl)methanide anion to dioxetane (2) produced initially ail unstable dioxetane bearing a phenylmethanide anion, decomposition of which gave light with maximum wavelength at 710-740 nm. Intramolecular cyclopropanation without decomposition of the dioxetane ring took place concurrently for the Michael reaction-induced decomposition of 2 with the bis(methoxycarbonyl)chloromethanide anion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.081

文献信息

• Fluoride-induced chemiluminescent decomposition of 1,2-dioxetanes bearing a phenyl moiety substituted with a methyl having an electron-withdrawing groupElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b2/b210857g/
  作者：Masakatsu Matsumoto、Toshiyuki Mizuno、Nobuko Watanabe

  DOI：10.1039/b210857g

  日期：2003.2.7

  A new type of dioxetane bearing a 3-(cyanomethyl)phenyl (1a), 3-(methoxycarbonylmethyl)phenyl (1b), 3-(benzoylmethyl)phenyl (1c), or 3-[cyano(methoxycarbonyl)methyl]phenyl group (1d) decomposed through an intermediary dioxetane bearing a benzylic carbanion to afford crimson to yellow light on treatment with TBAF in DMSO.

  一种新型二氧杂环丁烷，其含有3-(氰甲基)苯基(1a)、3-(甲氧羰基甲基)苯基(1b)、3-(苯甲酰甲基)苯基(1c)或3-[氰基(甲氧羰基)甲基]苯基团(1d)，通过具有苄基碳负离子的中间体二氧杂环丁烷分解，在DMSO中与TBAF处理后产生从绯红到黄色的光。