6,17-Bis[[tert-butyl(dimethyl)silyl]oxy]-9,14-dioxapentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione | 918314-88-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 6,17-Bis[[tert-butyl(dimethyl)silyl]oxy]-9,14-dioxapentacyclo[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-bis[[tert-butyl(dimethyl)silyl]oxy]-9,14-dioxapentacyclo[10.8.0.02,11.03,8.015,20]icosa-3(8),4,6,15(20),16,18-hexaene-10,13-dione
• CAS: 918314-88-2
• 化学式: C₃₀H₄₀O₆Si₂
• 分子量: 552.815
• InChiKey: MFRCVLSQRHHKPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.41
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,17-Bis[[tert-butyl(dimethyl)silyl]oxy]-9,14-dioxapentacyclo[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-((tert-butyldimethylsilyl)oxy)-2H-chromen-2-one
  参考文献：
  名称：

  Optimisation of two-photon induced cleavage of molecular linker systems for drug delivery

  摘要：

  Photoreactive linker systems for drug delivery in modern ophthalmology are crucial for the efficiency of such applications. We compare 5 different linker molecule candidates (truxillic acid and 4 dimers of coumarin derivates) in solution regarding their chemical stability and two-photon induced cleavage efficiency, and shed light into the role of molecular structure in the cleavage reaction. Dimers of the coumarin family showed much higher two-photon induced cleavage efficiency, achieving the highest reaction cross-section when tert-Butyldimethylsilyl (TBS) was used as a substituent, being almost 5-times higher than the unsubstituted coumarin dimer. Coumarin-based linker systems react promptly with nucleophilic solvents, in particular with short chain alcohols. The polarity of such solvents which do not cause a lactone ring opening seems not to influence the cleavage of the cyclobutane ring in coumarin dimers. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2009.12.016

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.