6,17-Dimethoxy-9,9,14,14-tetramethylpentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione | 1262108-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,17-Dimethoxy-9,9,14,14-tetramethylpentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione
• 英文别名: 6,17-dimethoxy-9,9,14,14-tetramethylpentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione
• CAS: 1262108-75-7
• 化学式: C₂₆H₂₈O₄
• 分子量: 404.506
• InChiKey: WWEROAWXJFWGIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,17-Dimethoxy-9,9,14,14-tetramethylpentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione 以 乙腈 为溶剂， 生成 7-methoxy-1,1-dimethylnaphthalenone
  参考文献：
  名称：

  1,1-Dimethylnaphthalenon-dimers as photocleavable linkers with improved two-photon-absorption efficiency and hydrolytic stability

  摘要：

  Coumarins are well known for reversible dimer formation with wavelengths greater than 300 nm and dimer cleavage below 300 nm. In a photochemical [2+2]-cycloaddition a cyclobutane ring is formed. Formation as well as cleavage of the cyclobutane ring may be accomplished by a single-photon-absorption as well as by a two-photon-absorption triggered reaction. The coumarin system is of interest for various kinds of applications, ranging from drug delivery for ophthalmic implants to optical data storage. However, the two-photon-absorption coefficient of coumarin dimers is rather low falling in the range of 1 GM in the visible range. We present here a substitute for the coumarin dinner system which not only has an about one order of magnitude higher two-photon-absorption coefficient, but also overcomes several other problems of the coumarin dimer system. Coumarines and in particular coumarine dimers have a very limited solubility in common solvents and are susceptible to hydrolysis of the lactone ring, which leads to an undesired complexity in the photochemical cleavage reaction. The 1,1-dimethylnaphtalenone dimers introduced here show excellent stability, lead only to a single cleavage product,and have a two-photon-absorption coefficient of about 10 GM at 532 nm. These properties make the 1,1-dimethylnaphtalenone dimers a superior substitute over the well-known coumarin dimers in particular in applications where two-photon-absorption induced photocleavage is required. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2009.11.005
• 作为产物：
  描述：

  7-methoxy-1,1-dimethylnaphthalenone 在 二苯甲酮 作用下， 以 氯仿 为溶剂， 反应 192.0h， 以72%的产率得到6,17-Dimethoxy-9,9,14,14-tetramethylpentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione
  参考文献：
  名称：

  1,1-Dimethylnaphthalenon-dimers as photocleavable linkers with improved two-photon-absorption efficiency and hydrolytic stability

  摘要：

  Coumarins are well known for reversible dimer formation with wavelengths greater than 300 nm and dimer cleavage below 300 nm. In a photochemical [2+2]-cycloaddition a cyclobutane ring is formed. Formation as well as cleavage of the cyclobutane ring may be accomplished by a single-photon-absorption as well as by a two-photon-absorption triggered reaction. The coumarin system is of interest for various kinds of applications, ranging from drug delivery for ophthalmic implants to optical data storage. However, the two-photon-absorption coefficient of coumarin dimers is rather low falling in the range of 1 GM in the visible range. We present here a substitute for the coumarin dinner system which not only has an about one order of magnitude higher two-photon-absorption coefficient, but also overcomes several other problems of the coumarin dimer system. Coumarines and in particular coumarine dimers have a very limited solubility in common solvents and are susceptible to hydrolysis of the lactone ring, which leads to an undesired complexity in the photochemical cleavage reaction. The 1,1-dimethylnaphtalenone dimers introduced here show excellent stability, lead only to a single cleavage product,and have a two-photon-absorption coefficient of about 10 GM at 532 nm. These properties make the 1,1-dimethylnaphtalenone dimers a superior substitute over the well-known coumarin dimers in particular in applications where two-photon-absorption induced photocleavage is required. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2009.11.005

文献信息

• 1,1-Dimethylnaphthalenon-dimers as photocleavable linkers with improved two-photon-absorption efficiency and hydrolytic stability
  作者：Julia Liese、Norbert A. Hampp

  DOI：10.1016/j.jphotochem.2009.11.005

  日期：2010.1

  Coumarins are well known for reversible dimer formation with wavelengths greater than 300 nm and dimer cleavage below 300 nm. In a photochemical [2+2]-cycloaddition a cyclobutane ring is formed. Formation as well as cleavage of the cyclobutane ring may be accomplished by a single-photon-absorption as well as by a two-photon-absorption triggered reaction. The coumarin system is of interest for various kinds of applications, ranging from drug delivery for ophthalmic implants to optical data storage. However, the two-photon-absorption coefficient of coumarin dimers is rather low falling in the range of 1 GM in the visible range. We present here a substitute for the coumarin dinner system which not only has an about one order of magnitude higher two-photon-absorption coefficient, but also overcomes several other problems of the coumarin dimer system. Coumarines and in particular coumarine dimers have a very limited solubility in common solvents and are susceptible to hydrolysis of the lactone ring, which leads to an undesired complexity in the photochemical cleavage reaction. The 1,1-dimethylnaphtalenone dimers introduced here show excellent stability, lead only to a single cleavage product,and have a two-photon-absorption coefficient of about 10 GM at 532 nm. These properties make the 1,1-dimethylnaphtalenone dimers a superior substitute over the well-known coumarin dimers in particular in applications where two-photon-absorption induced photocleavage is required. (C) 2009 Elsevier B.V. All rights reserved.