anti-[1,2:9,10]-dibenzo-5,13-di-tert-butyl-8,16-dimethyl[2.2]metacyclophane | 181486-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: anti-[1,2:9,10]-dibenzo-5,13-di-tert-butyl-8,16-dimethyl[2.2]metacyclophane
• 英文别名: 10,21-Ditert-butyl-23,24-dimethylpentacyclo[17.3.1.18,12.02,7.013,18]tetracosa-1(22),2,4,6,8,10,12(24),13,15,17,19(23),20-dodecaene
• CAS: 181486-14-6
• 化学式: C₃₄H₃₆
• 分子量: 444.66
• InChiKey: DGOAFZYKWTVWJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  anti-[1,2:9,10]-dibenzo-5,13-di-tert-butyl-8,16-dimethyl[2.2]metacyclophane 以 氘代四氢呋喃 为溶剂， 反应 0.17h， 以35%的产率得到(3a1s,7b1s)-2,9-di-tert-butyl-3a1,7b1-dimethyl-3a1,7b1-dihydrodibenzo[fg,op]tetracene
  参考文献：
  名称：

  Synthesis of the elusive dibenzannelated dihydropyrene dibenzo[e,l]dimethyldihydropyrene, a molecular photo-switch

  摘要：

  Synthesis of the unknown o-m-o-m-cyclophane derivative 13 is achieved by deoxygenation of the adduct 12, derived from a bis-Diels-Alder addition of furan to the intermediate bis-aryne generated by bis-dehydrobromination of dibromide 11. The colorless photochromic cyclophanediene 13 switches to the green dibenzannulene 14 on uv irradiation, and 14 thermally or photochemically reverts to 13, with E(act) = 20 kcal/mole. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)01074-x
• 作为产物：
  描述：

  anti-6,13-di-tert-butyl-1,4:8,11-diepoxy-trans-14b,14c-dimethyl-1,4,8,11,14b,14c-hexahydrodibenzo[fg,op]naphthacene 在 diiron nonacarbonyl 作用下， 以 苯 为溶剂， 以68%的产率得到anti-[1,2:9,10]-dibenzo-5,13-di-tert-butyl-8,16-dimethyl[2.2]metacyclophane
  参考文献：
  名称：

  Synthesis of the elusive dibenzannelated dihydropyrene dibenzo[e,l]dimethyldihydropyrene, a molecular photo-switch

  摘要：

  Synthesis of the unknown o-m-o-m-cyclophane derivative 13 is achieved by deoxygenation of the adduct 12, derived from a bis-Diels-Alder addition of furan to the intermediate bis-aryne generated by bis-dehydrobromination of dibromide 11. The colorless photochromic cyclophanediene 13 switches to the green dibenzannulene 14 on uv irradiation, and 14 thermally or photochemically reverts to 13, with E(act) = 20 kcal/mole. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)01074-x

文献信息

• Synthesis and Photochromic Properties of Molecules Containing [<i>e</i>]-Annelated Dihydropyrenes. Two and Three Way π-Switches Based on the Dimethyldihydropyrene−Metacyclophanediene Valence Isomerization
  作者：Reginald H. Mitchell、Timothy R. Ward、Yongsheng Chen、Yunxia Wang、S. Ananda Weerawarna、Peter W. Dibble、Michael J. Marsella、Adah Almutairi、Zhi-Qiang Wang

  DOI：10.1021/ja0288136

  日期：2003.3.1

  more than one photochromic switch present and thus have more than a simple "on-off" state. Thermodynamic data are obtained for the thermal closing reactions. The anthrodihydropyrene (12) has the fastest thermal closing (tau(1/2) = 20 min), while the furanodihydropyrene (19') has the slowest (tau(1/2) = 63 h) at 46 degrees C. An electrochemical readout of the state of the switch is demonstrated for the

  描述了几种新的简单负片、一个简单正片和多个负片光致变色材料的合成，这些光色素包含二氢芘-环芳二烯光致变色系统。母体 2,7-di-的 [e]-退火苯并 (7)、萘并 (9)、蒽 (11)、呋喃 (19) 和三苯并 (15) 衍生物的光开孔叔丁基-反式 10b,10c-二甲基-二氢芘 (5) 及其 4,5-二溴衍生物 (13) 被描述为提供相应的环芳二烯，以及它们的光封闭和热封闭二氢芘。将这些与正性光致变色二苯并[e，l]二氢芘（21）和双（二氢芘）芘（44）和（二氢芘苯并）（苯并）间环芘（47）光致变色的结果进行比较，它们具有多个光致变色开关，因此不仅仅是简单的“开-关”状态。获得热闭合反应的热力学数据。蒽二氢芘 (12) 的热闭合速度最快 (tau(1/2) = 20 分钟)，而呋喃二氢芘 (19') 的热闭合最慢 (tau(1/2) = 63 h) 在 46 摄氏度。对苯并二氢芘 (7)
• Multistate π Switches:  Synthesis and Photochemistry of a Molecule Containing Three Switchable Annelated Dihydropyrene Units
  作者：Reginald H. Mitchell、Cornelia Bohne、Yunxia Wang、Subhajit Bandyopadhyay、Chelsea B. Wozniak

  DOI：10.1021/jo052153g

  日期：2006.1.1

  The synthesis of the multistate photochromic switch 3 is described. This switch contains three dihydropyrene (DHP) units in the most conjugated fully closed form 3-c,c,c. The thermally stable form has the central DHP unit open and is 3-c,o,c. NMR and laser flash photolysis experiments were used to characterize the multiple states in the photoswitching of 3 by visible and UV light. Three of the possible five isomeric states of 3-c,o,c were observed. Irradiation of 3-c,o,c by visible light led to the formation of 3-o,o,o via the isomer 3-c,o,o as an intermediate, which were observed by NMR. Irradiation by UV light led to the formation of 3-c,c,c, which decays with a lifetime of 7.5 ms.