5,6-Bis(2,5-dimethylthiophen-3-yl)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione | 862260-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 5,6-Bis(2,5-dimethylthiophen-3-yl)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione
• CAS: 862260-09-1
• 化学式: C₂₀H₂₀O₃S₂
• 分子量: 372.509
• InChiKey: QKIAOYBOWJWBPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-Bis(2,5-dimethylthiophen-3-yl)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione 以 乙腈 为溶剂， 生成 4,6,7,9-Tetramethyl-16-oxa-5,8-dithiapentacyclo[10.7.0.02,6.07,11.014,18]nonadeca-1,3,9,11-tetraene-15,17-dione
  参考文献：
  名称：

  Reactivity-Gated Photochromism of 1,2-Dithienylethenes for Potential Use in Dosimetry Applications

  摘要：

  A novel molecular switching system based on reactivity-gated photochromism operates because a butadiene undergoes a [4 + 2] cycloaddition reaction with a dienophile to produce the photoresponsive 1,2-dithienylethene backbone. The reversible change in color when samples are irradiated with appropriate wavelengths of light occurs only after the Diels-Alder cycloaddition reaction takes place.

  DOI：

  10.1021/ol050971p
• 作为产物：
  描述：

  1,2-bis[2,5-dimethyl(3-thienyl)]ethane-1,2-dione 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 5,6-Bis(2,5-dimethylthiophen-3-yl)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione
  参考文献：
  名称：

  Reactivity-Gated Photochromism of 1,2-Dithienylethenes for Potential Use in Dosimetry Applications

  摘要：

  A novel molecular switching system based on reactivity-gated photochromism operates because a butadiene undergoes a [4 + 2] cycloaddition reaction with a dienophile to produce the photoresponsive 1,2-dithienylethene backbone. The reversible change in color when samples are irradiated with appropriate wavelengths of light occurs only after the Diels-Alder cycloaddition reaction takes place.

  DOI：

  10.1021/ol050971p

文献信息

• PHOTOCHROMIC AND ELECTROCHROMIC COMPOUNDS AND SYNTHESIS AND USE THEREOF
  申请人：Branda Neil R.

  公开号：US20100190868A1

  公开（公告）日：2010-07-29

  Novel photochromic and electrochromic hexadiene compounds are described. The compounds are reversibly convertible between ring-open and ring-closed isomeric forms as indicated in structures I(o) and I(c) below. (See formula in original abstract of application) The conversion between the different isomeric forms may be induced by light or electricity. In one embodiment the compounds may include a charge transfer moiety including electron donor and acceptor groups. The electron donor and acceptor are linearly conjugated in the ring-open form to enable electron transfer but are electrically insulated in the ring-closed form. Methods for synthesizing the compounds from photochemically and/or electrically inert precursors are also described. For example, the photoresponsive compounds may be synthesized by reacting diene precursors with dienophiles in a condensation reaction. The compounds may be utilized in reactivity-gated photochromic or electrochromic applications. In one embodiment of the invention, compounds of the invention may be used in a method to selectively release a releasable agent, such as a small molecule. According to this method, a photochemically inert precursor compound is reacted with the releasable agent to form a carrier compound comprising a switching moiety, the switching moiety being reversibly convertible between a thermally unstable form and a thermally stable form. The switching moiety may be selectively converted between the first and second forms to cause controlled release of the releasable agent from the carrier compound.

  本文描述了新型的光致变色和电致变色六烯基化合物。这些化合物可以在开环和闭环异构形式之间可逆转化，如下所示的结构I（o）和I（c）。 （请参见申请书原摘要中的公式）不同异构形式之间的转化可以通过光或电引发。在一种实施例中，这些化合物可以包括一个电荷转移基团，包括电子给体和受体基团。在开环形式中，电子给体和受体是线性共轭的，以实现电子转移，但在闭环形式中是电绝缘的。本文还描述了从光化学和/或电化学惰性前体合成这些化合物的方法。例如，可以通过将二烯前体与二烯酰亲合剂在缩合反应中反应来合成光响应化合物。这些化合物可以用于反应门控的光致变色或电致变色应用中。在本发明的一种实施例中，本发明的化合物可以用于选择性释放可释放剂（例如小分子）的方法。根据这种方法，将光化学惰性前体化合物与可释放剂反应以形成载体化合物，其中载体化合物包含可转换为热不稳定形式和热稳定形式的开关基团。可以选择性地在第一和第二形式之间转换开关基团，以从载体化合物中控制释放可释放剂。
• WO2006/125317
  申请人：——

  公开号：——

  公开（公告）日：——
• US8536205B2
  申请人：——

  公开号：US8536205B2

  公开（公告）日：2013-09-17
• Reactivity-Gated Photochromism of 1,2-Dithienylethenes for Potential Use in Dosimetry Applications
  作者：Vincent Lemieux、Neil R. Branda

  DOI：10.1021/ol050971p

  日期：2005.7.1

  A novel molecular switching system based on reactivity-gated photochromism operates because a butadiene undergoes a [4 + 2] cycloaddition reaction with a dienophile to produce the photoresponsive 1,2-dithienylethene backbone. The reversible change in color when samples are irradiated with appropriate wavelengths of light occurs only after the Diels-Alder cycloaddition reaction takes place.