cis,syn-cyclobutadiindene | 25456-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: cis,syn-cyclobutadiindene
• 英文别名: 4b,4c,9,9a,9b,10-hexahydrocyclobuta[1,2-a:4,3-a']diindene；syn-Kopf-Kopf-cyclobutdiinden；(1S,2R,10R,11S)-pentacyclo[9.7.0.02,10.03,8.013,18]octadeca-3,5,7,13,15,17-hexaene
• CAS: 25456-57-9
• 化学式: C₁₈H₁₆
• 分子量: 232.325
• InChiKey: CCYRGSGMKDEJFK-USTZCAOPSA-N

物化性质

• 沸点：
  353.4±32.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

上下游信息

反应信息

• 作为反应物：
  描述：

  cis,syn-cyclobutadiindene 在 DCNB 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 exo-1-nitro-endo-2-phenyl-1,1a,2,2a-tetrahydro-7H-cyclobutindene
  参考文献：
  名称：

  Redox-photosensitized reactions. 5. Redox-photosensitized ring cleavage of 1,1a,2,2a-tetrahydro-7H-cyclobut[a]indene derivatives: mechanism and structure-reactivity relationship

  摘要：

  DOI：

  10.1021/ja00536a025
• 作为产物：
  描述：

  茚 在 二茂铁 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以32%的产率得到cis,syn-cyclobutadiindene
  参考文献：
  名称：

  Redox-photosensitized reactions. 5. Redox-photosensitized ring cleavage of 1,1a,2,2a-tetrahydro-7H-cyclobut[a]indene derivatives: mechanism and structure-reactivity relationship

  摘要：

  DOI：

  10.1021/ja00536a025

文献信息

• Photodimerization of hydrophobic guests within a water-soluble nanocapsule
  作者：Anand Parthasarathy、Shampa R. Samanta、V. Ramamurthy

  DOI：10.1007/s11164-012-0633-7

  日期：2013.1

  Conducting reactions in environmentally benign conditions is one of the major objectives of “green chemistry.” In this context, developing ways to conduct reactions in water seems obvious. In this report, we present our results on photodimerization of select guest molecules placed within the rigid reaction cavity of a water-soluble cavitand, octa acid. The results presented herein highlight the value of a supramolecular approach in achieving selectivity in photoreactions and opening reaction pathways that are latent in solution chemistry.

  在对环境无害的条件下进行反应是 "绿色化学 "的主要目标之一。在这种情况下，开发在水中进行反应的方法似乎显而易见。在本报告中，我们介绍了置于水溶性空穴剂辛酸的刚性反应腔内的精选客体分子的光二聚化结果。本文介绍的结果凸显了超分子方法在实现光反应选择性和打开溶液化学潜在反应途径方面的价值。
• Photochemical Reactions of Aromatic Compounds. XXXIII. Photoreactions of 1-Cyanonaphthalene with Indene in Various Solvents
  作者：Masahide Yasuda、Chyongjin Pac、Hiroshi Sakurai

  DOI：10.1246/bcsj.53.502

  日期：1980.2

  accompanied by the formation of 2-methoxyindan and 2,2′-dimethoxy-1,1′-biindanyl or 2-indanol and 1-hydroxy-2,2′-biindanyl. In these solvents, the reactions were suggested to be initiated by photochemical electron transfer; the methoxylated or hydroxylated compounds are formed by the nucleophilic attack of methanol or water on the indene cation. Anionic species, including the 1-cyanonaphthalene anion, were

  1-氰基萘与茚的立体有择光环加成反应发生在环己烷、苯、乙醚、四氢呋喃和乙酸乙酯中，得到内端头对头环加成物作为唯一的 1:1 加成物。该机制是根据激基复合物中介进行讨论的。在甲醇或乙腈中，在水存在下，光反应得到二氢环加合物 (8)，同时形成 2-甲氧基茚满和 2,2'-二甲氧基-1,1'-二茚满基或 2-茚满醇和 1-羟基-2,2'-联茚基。在这些溶剂中，反应被认为是由光化学电子转移引发的；通过甲醇或水对茚阳离子的亲核攻击形成甲氧基化或羟基化化合物。阴离子物质，包括 1-氰基萘阴离子，被认为在 8 的形成中起重要作用。
• Organophotocatalytic [2+2] Cycloaddition of Electron‐Deficient Styrenes**
  作者：Maxim Golfmann、Louis Glagow、Antonios Giakoumidakis、Christopher Golz、Johannes C. L. Walker

  DOI：10.1002/chem.202202373

  日期：2023.1.12

  The [2+2] cycloaddition of alkenes is a powerful method of preparing cyclobutanes, but the use of electron-deficient styrenes has been largely neglected so far. By using the organophotocatalyst 4CzIPN, a visible-light-mediated procedure to cyclobutane motifs bearing electron-deficient aryl substituents has been developed. Homodimerisations as well as intramolecular reactions to fused bicyclic motifs

  烯烃的[2+2] 环加成是制备环丁烷的有效方法，但迄今为止，缺电子苯乙烯的使用在很大程度上被忽视了。通过使用有机光催化剂 4CzIPN，开发了一种可见光介导的方法来处理带有缺电子芳基取代基的环丁烷基序。同二聚化以及融合双环基序的分子内反应可以以良好到极好的收率进行。
• Metzner,W.; Wendisch,D., Justus Liebigs Annalen der Chemie, 1969, vol. 730, p. 111 - 120
  作者：Metzner,W.、Wendisch,D.

  DOI：——

  日期：——
• Water-soluble octa acid capsule as a reaction container: Templated photodimerization of indene in water
  作者：Anand Parthasarathy、V. Ramamurthy

  DOI：10.1016/j.jphotochem.2015.11.005

  日期：2016.2

  In the context of green chemistry, identifying strategies to carry out organic reactions in aqueous medium in the absence of organic and inorganic reagents is important. We show below that octa acid (OA), a water-soluble cavitand, is capable of solubilizing water insoluble reactant in water and yielding selective product by confining the reactants and intermediates during a light initiated reaction. By employing indene as the substrate we have observed that the OA capsule upon irradiation facilitates the formation of anti-head-tail dimer, the isomer that is generally not obtained upon direct excitation and triplet and electron transfer sensitizations in isotropic organic solvents. (C) 2015 Elsevier B.V. All rights reserved.