2-(tert-butyl)-11,12-didehydro-8-methoxy-6H-dibenzo[b,f]oxocine | 1403778-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(tert-butyl)-11,12-didehydro-8-methoxy-6H-dibenzo[b,f]oxocine
• 英文别名: oxodibenzocyclooctyne；14-Tert-butyl-6-methoxy-2-oxatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yne；14-tert-butyl-6-methoxy-2-oxatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yne
• CAS: 1403778-15-3
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: JKHIEZXMKXUSEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-(tert-butyl)-11,12-didehydro-8-methoxy-6H-dibenzo[b,f]oxocine 、 3'-[[3-[3-(2-Azidoethoxy)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methoxy]-6'-[(3-hydroxynaphthalen-2-yl)methoxy]spiro[2-benzofuran-3,9'-xanthene]-1-one 以 甲醇 为溶剂， 生成 3'-[[3-[3-[2-(9-Tert-butyl-17-methoxy-13-oxa-3,4,5-triazatetracyclo[13.4.0.02,6.07,12]nonadeca-1(15),2(6),4,7(12),8,10,16,18-octaen-3-yl)ethoxy]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methoxy]-6'-[(3-hydroxynaphthalen-2-yl)methoxy]spiro[2-benzofuran-3,9'-xanthene]-1-one
  参考文献：
  名称：

  Photoactivatable Fluorescein Derivatives Caged with a (3-Hydroxy-2-naphthalenyl)methyl Group

  摘要：

  The (3-hydroxy-2-naphthalenyl)methyl (NQMP) group represents an efficient photocage for fluorescein-based dyes. Thus, irradiation of the 6-NQMP ether of 2'-hydroxymethylfluorescein with low-intensity UVA light results in a 4-fold increase in emission intensity. Photoactivation of nonfluorescent NQMP-caged 3-allyloxyfluorescein produces a highly emissive fluorescein monoether. To facilitate conjugation of the caged dye to the substrate of interest via click chemistry, the allyloxy appendage was functionalized with an azide moiety.

  DOI：

  10.1021/jo501116g
• 作为产物：
  描述：

  间甲氧基苯甲醇 在 aluminum (III) chloride 、 三溴化磷 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.38h， 生成 2-(tert-butyl)-11,12-didehydro-8-methoxy-6H-dibenzo[b,f]oxocine
  参考文献：
  名称：

  Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations

  摘要：

  氧杂二苯并环辛炔（ODIBO，2a-c）是通过相应的环丙烯酮（光-ODIBO，1a-c）的光化学脱羰基反应制备的。虽然光-ODIBO 不与叠氮化物反应，但 ODIBO 是活性最高的环辛炔之一，在水溶液中的环加成速率超过 45 M-1 s-1。ODIBO 在环境条件下很稳定，对硫醇的反应性很低。光-ODIBO 在加热至 160 °C 时仍能存活，并且不会与硫醇发生反应。

  DOI：

  10.1039/c2ob26581h

文献信息

• Photoactivatable Fluorescein Derivatives Caged with a (3-Hydroxy-2-naphthalenyl)methyl Group
  作者：Emmanuel E. Nekongo、Vladimir V. Popik

  DOI：10.1021/jo501116g

  日期：2014.8.15

  The (3-hydroxy-2-naphthalenyl)methyl (NQMP) group represents an efficient photocage for fluorescein-based dyes. Thus, irradiation of the 6-NQMP ether of 2'-hydroxymethylfluorescein with low-intensity UVA light results in a 4-fold increase in emission intensity. Photoactivation of nonfluorescent NQMP-caged 3-allyloxyfluorescein produces a highly emissive fluorescein monoether. To facilitate conjugation of the caged dye to the substrate of interest via click chemistry, the allyloxy appendage was functionalized with an azide moiety.
• Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations
  作者：Christopher D. McNitt、Vladimir V. Popik

  DOI：10.1039/c2ob26581h

  日期：——

  Oxa-dibenzocyclooctynes (ODIBO, 2a–c) are prepared by photochemical decarbonylation of corresponding cyclopropenones (photo-ODIBO, 1a–c). While photo-ODIBO does not react with azides, ODIBO is one of the most reactive cyclooctynes exhibiting rates of cycloaddition over 45 M−1 s−1 in aqueous solutions. ODIBO is stable under ambient conditions and has low reactivity towards thiols. Photo-ODIBO survives heating up to 160 °C and does not react with thiols.

  氧杂二苯并环辛炔（ODIBO，2a-c）是通过相应的环丙烯酮（光-ODIBO，1a-c）的光化学脱羰基反应制备的。虽然光-ODIBO 不与叠氮化物反应，但 ODIBO 是活性最高的环辛炔之一，在水溶液中的环加成速率超过 45 M-1 s-1。ODIBO 在环境条件下很稳定，对硫醇的反应性很低。光-ODIBO 在加热至 160 °C 时仍能存活，并且不会与硫醇发生反应。