2-bromo-3-chloronorbornadiene | 128780-26-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-bromo-3-chloronorbornadiene
• 英文别名: 2-bromo-3-chloromorbornadiene；2-chloro-3-bromo-norbornadiene；2-bromo-3-chlorobicyclo[2.2.1]hepta-2,5-diene
• CAS: 128780-26-7
• 化学式: C₇H₆BrCl
• 分子量: 205.482
• InChiKey: LQJYBSLPWXFMCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-bromo-3-chloronorbornadiene 在 苯乙酮 作用下， 以 乙醚 为溶剂， 以66%的产率得到1-bromo-5-chlorotetracyclo[3.2.0.02,7.04,6]heptane
  参考文献：
  名称：

  Generation and trapping of 1,5-dehydroquadricyclane

  摘要：

  DOI：

  10.1021/ja00172a031
• 作为产物：
  描述：

  2-chloro-3-lithionorbornadiene 在 1,2-二溴乙烷 作用下， 生成 2-bromo-3-chloronorbornadiene
  参考文献：
  名称：

  Generation and trapping of 1,5-dehydroquadricyclane

  摘要：

  DOI：

  10.1021/ja00172a031

文献信息

• Synthesis of 2,3-disubstituted norbornadienes
  作者：Geoffrey K Tranmer、Carol Yip、Sean Handerson、Robert W Jordan、William Tam

  DOI：10.1139/v00-047

  日期：2000.5.1

  Various 2,3-disubstituted norbornadienes that can hardly be made by the traditional Diels-Alder method were synthesized by double lithium halide exchange of 2,3-dibromonorbornadiene in moderate to good yields.Key words: 2,3-disubstituted norbornadienes, Diels-Alder reaction, lithium halide exchange.

  通过对2,3-二溴去氢莰烯进行双锂卤化物交换，合成了各种传统Diels-Alder方法难以制备的2,3-二取代莰烯，产率在中等到良好之间。关键词：2,3-二取代莰烯，Diels-Alder反应，锂卤化物交换。
• Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrile Oxides
  作者：Carol Yip、Sean Handerson、Geoffrey K. Tranmer、William Tam

  DOI：10.1021/jo005611o

  日期：2001.1.1

  Efficient routes to the synthesis of norbornadiene-tethered nitrile oxides have been developed, and their intramolecular 1,3-dipolar cycloadditions were studied. The cycloadditions occurred in good yields for a variety of substrates and were found to be highly regio- and stereoselective, giving single regio- and stereoisomers in most cases.

  已经开发了合成降冰片二烯系氮氧化物的有效途径，并且研究了它们的分子内1，3-偶极环加成反应。对于多种底物，环加成反应的收率很高，并且被发现具有很高的区域和立体选择性，在大多数情况下可得到单一的区域和立体异构体。
• Norbornadiene-bridged diarylethenes and their conversion into turn-off fluorescent photoswitches
  作者：Simon M. Büllmann、Andres Jäschke

  DOI：10.1039/d0cc02210a

  日期：——

  A new class of reversible fluorogenic diarylethenes, assembled by iEDDA chemistry, with high switching efficiencies and quantum yields is described.

  一种新型可逆荧光二芳基乙烯类化合物，由iEDDA化学方法组装而成，具有高开关效率和量子产率。
• Diaryl-substituted norbornadienes with red-shifted absorption for molecular solar thermal energy storage
  作者：Victor Gray、Anders Lennartson、Phasin Ratanalert、Karl Börjesson、Kasper Moth-Poulsen

  DOI：10.1039/c3cc47517d

  日期：——

  Red-shifting the absorption of norbornadienes (NBDs), into the visible region, enables the photo-isomerization of NBDs to quadricyclanes (QCs) to be driven by sunlight. This is necessary in order to utilize the NBD–QC system for molecular solar thermal (MOST) energy storage. Reported here is a study on five diaryl-substituted norbornadienes. The introduced aryl-groups induce a significant red-shift of the UV/vis absorption spectrum of the norbornadienes, and device experiments using a solar-simulator set-up demonstrate the potential use of these compounds for MOST energy storage.

  将降冰片二烯（NBDs）的吸收红移到可见光区域，可使 NBDs 在阳光的驱动下光异构化为四环（QCs）。这对于利用 NBD-QC 系统进行分子太阳能热（MOST）储能是非常必要的。本文报告了对五种二芳基取代的降冰片二烯的研究。引入的芳基使降冰片二烯的紫外/可见吸收光谱发生了显著的红移，使用太阳能模拟装置进行的设备实验证明了这些化合物用于 MOST 储能的潜力。
• Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrones
  作者：Geoffrey K. Tranmer、William Tam

  DOI：10.1021/jo015610b

  日期：2001.7.1

  Efficient routes to the synthesis of norbornadiene-tethered nitrones have been developed, and their intramolecular 1,3-dipolar cycloadditions were studied. The cycloadditions occurred in moderate to good yields for a variety of substrates and were found to be highly regio- and stereoselective, giving single regio- and stereoisomers in most cases.