4,5,9,10-tetrabromo-2,7-di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene | 76447-51-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4,5,9,10-tetrabromo-2,7-di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene
• CAS: 76447-51-3
• 化学式: C₂₆H₂₈Br₄
• 分子量: 660.124
• InChiKey: UGVBPERXRKQBKL-DIVCQZSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.15
• 重原子数：
  30.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4,5,9,10-tetrabromo-2,7-di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene 反应 0.08h， 以55%的产率得到(3aS,10bS)-4,5,9,10-Tetrabromo-2,7-di-tert-butyl-3a,10b-dimethyl-3a,10b-dihydro-pyrene
  参考文献：
  名称：

  Metacyclophanes and related compounds. 5. Thermal rearrangement of 10b,10c-dialkyl-2,7-di-tert-butyl-trans-10b,10c-dihydropyrenes

  摘要：

  DOI：

  10.1021/jo00135a020
• 作为产物：
  描述：

  5,13-di-tert-butyl-8,16-dimethyl[2,2]metacyclophan-1-ene 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.02h， 以87.8%的产率得到4,5,9,10-tetrabromo-2,7-di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene
  参考文献：
  名称：

  Metacyclophanes and related compounds. 4. Halogenations of 8,16-dialkyl-anti-5,13-di-tert-butyl[2.2]metacyclophan-1-enes and 2,7-di-tert-butyl-trans-10b,10c-dialkyl-10b,10c-dihydropyrenes

  摘要：

  DOI：

  10.1021/ja00377a027

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)
• HALOGENATION OF 2,7-DI-<i>TERT</i>-BUTYL-<i>TRANS</i>-10b,10c-DIALKYL-10b,10c-DIHYDROPYRENES
  作者：Masashi Tashiro、Takehiko Yamato

  DOI：10.1246/cl.1980.1127

  日期：1980.9.5

  Treatment of 2,7-di-tert-butyl-trans-10b,10c-dialkyl-10b,10c-dihydropyrene 5a–5c with bromine afforded the corresponding tetrabromides 7a–7c in good yields, respectively. The tetrachloro derivative of 5a was also obtained in 40% yield by the treatment of 5a with SO2Cl2. The bromination of 5a–5c with bromine in the presence of Fe powder gave the dealkylated compound 2,7-di-tert-4,5,9,10-tetrabromopyrene 8 in good yields, respectively. When 5a–5c were treated with I2 2,7-di-tert-butylpyrene 9 was obtained in good yields, in all cases.

  用溴处理 2,7-二叔丁基-反式-10b,10c-二烷基-10b,10c-二氢芘 5a-5c，可分别得到相应的四溴化物 7a-7c，收率很高。用 SO2Cl2 处理 5a 也能得到 5a 的四氯衍生物，收率为 40%。在有铁粉存在的情况下，用溴对 5a-5c 进行溴化，分别得到了脱烷基化合物 2,7-二叔丁基-4,5,9,10-四溴芘 8，收率很高。当 5a-5c 用 I2 处理时，在所有情况下都能以良好的产率得到 2,7-二叔丁基芘 9。
• Selective preparation. 30. A convenient preparation of 5,13-di-tert-butyl-8,16-disubstituted-[2.2]metacyclophanes and their trans-tert-butylation and halogenation reactions
  作者：Masashi Tashiro、Takehiko Yamato

  DOI：10.1021/jo00321a005

  日期：1981.4
• Dimethyldihydropyrene−Dehydrobenzoannulene Hybrids:  Studies in Aromaticity and Photoisomerization
  作者：David B. Kimball、Michael M. Haley、Reginald H. Mitchell、Timothy R. Ward、Subhajit Bandyopadhyay、Richard Vaughan Williams、John R. Armantrout

  DOI：10.1021/jo020462q

  日期：2002.12.1

  The synthesis and study of dehydrobenzoannulene (DBA)-dimethyldihydropyrene (DDP) hybrids as models for the investigation of aromaticity in weakly diatropic systems is reported. Three new monofused DBA-DDP hybrids have been synthesized, and their NMR spectra are discussed with regard to quantifying the aromaticity remaining in multibenzene-fused DBAs. Nucleus-independent chemical shifts, determined at a series of locations for each compound, bond lengths, and H-1 and C-13 NMR chemical shifts were calculated and used to probe the aromaticity of these hybrids. Systems where more than one annulene/DBA is fused to the DDP core have also been obtained, and their potential use in photoinduced isomerization applications is discussed.
• Dehydrobenzoannulene−Dimethyl- dihydropyrene Hybrids:  Model Systems for the Synthesis of Molecular Aromatic Probes
  作者：David B. Kimball、Michael M. Haley、Reginald H. Mitchell、Timothy R. Ward

  DOI：10.1021/ol015898r

  日期：2001.5.1

  Synthesis of two novel dehydrobenzoannulene-dimethyldihydropyrene (DBA-DDP) hybrids has been achieved using a Pd/Cu cross-coupling strategy.