4-(1'-naphthoyl)-2,7-di-tert-butyl-10b,10c-dimethyl-trans-10b,10c-dihydropyrene

• 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-(1'-naphthoyl)-2,7-di-tert-butyl-10b,10c-dimethyl-trans-10b,10c-dihydropyrene
• 英文别名: 2,7-di-tert-butyl-4-(1-naphthoyl)-trans-10b,10c-dimethyl-10b,10c-dihydropyrene；[(10bR,10cR)-2,7-ditert-butyl-10b,10c-dimethylpyren-4-yl]-naphthalen-1-ylmethanone
• 化学式: C₃₇H₃₈O
• 分子量: 498.708
• InChiKey: RAZFKOSDKXUFAY-FZNHDDJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(1'-naphthoyl)-2,7-di-tert-butyl-10b,10c-dimethyl-trans-10b,10c-dihydropyrene 以 氘代氯仿 为溶剂， 生成
  参考文献：
  名称：

  The Effect of Addition of Fluorescent Moieties to Dihydropyrenes:  Enhancing Photochromicity and Fluorescence Monitoring

  摘要：

  A series of dihydropyrenes with appending fluorescent moieties were synthesized with the objective of increasing the photochromic efficiency for this class of compounds and to establish how suitable fluorescence would be to follow their photochromic behavior. The ring opening quantum yields of dihydropyrenes with aroyl substituents at the 4-position showed increased ring opening quantum yields without a decrease of the half-life for the thermal reversion of the less stable open isomer, the metacyclophanediene to the dihydropyrene. The fluorescence of the appending naphthoyl or pyrenoyl moieties was not suitable to follow the photochromic cycling of the dihydropyrenes. However, the emission detected above 600 nm of the closed isomer of the dihydropyrene moiety was shown to be a good monitoring method for the photochromic cycling.

  DOI：

  10.1021/jo0712392
• 作为产物：
  描述：

  生成 4-(1'-naphthoyl)-2,7-di-tert-butyl-10b,10c-dimethyl-trans-10b,10c-dihydropyrene
  参考文献：
  名称：

  The Effect of Addition of Fluorescent Moieties to Dihydropyrenes:  Enhancing Photochromicity and Fluorescence Monitoring

  摘要：

  A series of dihydropyrenes with appending fluorescent moieties were synthesized with the objective of increasing the photochromic efficiency for this class of compounds and to establish how suitable fluorescence would be to follow their photochromic behavior. The ring opening quantum yields of dihydropyrenes with aroyl substituents at the 4-position showed increased ring opening quantum yields without a decrease of the half-life for the thermal reversion of the less stable open isomer, the metacyclophanediene to the dihydropyrene. The fluorescence of the appending naphthoyl or pyrenoyl moieties was not suitable to follow the photochromic cycling of the dihydropyrenes. However, the emission detected above 600 nm of the closed isomer of the dihydropyrene moiety was shown to be a good monitoring method for the photochromic cycling.

  DOI：

  10.1021/jo0712392

文献信息

• Platinum Complexes of Alkynyl-Substituted Dimethyldihydropyrenes
  作者：Pengrong Zhang、David J. Berg、Reginald H. Mitchell、Allen Oliver、Brian Patrick

  DOI：10.1021/om3007008

  日期：2012.12.10

  precursors to ethynyl ligands. Dehydrohalogenation of the adduct of these ethynes with various PtCl2(L)2 complexes afforded a series of cis and trans square-planar bis(DHP-ethynyl) platinum complexes, (RDHP-C≡C)2Pt(L)2 (cis, R = H, L2 = PEt3 (9), acetyl, PEt3 (10), benzoyl, PEt3 (11), 1-naphthoyl, PEt3 (12), benzo[e], PEt3 (13), benzoyl, PPh3 (14), benzo[e], PPh3 (15); trans, R = H, L2 = dppe (16), benzo[e]

  一系列光致变色dimethyldihydropyrenes的（DHP）在4位上轴承乙炔取代基（ř DHP-C≡CH; R = H（4），乙酰基（5），苯甲酰基（6），1-萘甲酰基（7），苯并[ e ]（8））被制备用作乙炔基配体的前体。这些乙炔与各种氯铂酸的加合物的脱卤化氢2（L）2种复合物，得到一系列的顺式和反式正方形平面双（DHP-乙炔基）铂络合物，（- [R DHP-C≡C）2铂（L）2（顺式，R = H，L 2 = PEt 3（9），乙酰基，PEt 3（10），苯甲酰基，PEt 3（11），1-萘甲酰基，PEt 3（12），苯并[ e ]，PEt 3（13），苯甲酰基，PPh 3（14），苯并[ e ]，PPh 3（15）；反式，R ＝ H，L 2＝ dppe（16），苯并[ e ]，dppe（17），乙酰基，联吡啶（18），1-萘甲酰基，联吡啶（19），H，phen（20））。DHP-乙炔带有酰基和苯并[
• Stable Ion NMR and GIAO-DFT Study of Novel Cations from 8,16-Dicyano[2.2]metacyclophanedienes and from Strategically Substituted/Benzannelated Dihydropyrenes:  Charge-Induced Tropicity Modulation and π-Switching
  作者：Kenneth K. Laali、Takao Okazaki、Reginald H. Mitchell、Khurshid Ayub、Rui Zhang、Stephen G. Robinson

  DOI：10.1021/jo701932j

  日期：2008.1.1

  [GRAPHICS]The dicyanometacyclophanediene 1 is diprotonated at the cyano groups (1H(2)(2+)) in various superacid media. Upon quenching, intact 1 and the ring-closed CPD 2 were obtained in a 3:2 or 3:1 ratio, depending on the superacid system. Compound 2 undergoes ring opening in the superacid to give the ipso-monoprotonated 2H(+), which on quenching furnishes 1-cyanopyrene as a major product together with 2 and 1. The dication 3(2+), with strongly deshielded internal methyls, was generated from the epoxyannulene 3. Ketones 4-6 and ester 7 are O/C diprotonated to give paratropic carboxonium-annulenium dications (4H(2)(2+), 5H(2)(2+), 6H(2)(2+), and -7H(2)(2+), respectively). Ester 8 gives a trication by two-electron oxidation and O-protonation. Conjugated carboxylic acid 9 gives a mixture of two dications by CO and ring protonation. The dibromo derivatives 10 and 11 form carboxoniurn ions, whereas the monobromo derivative 12 is O/C diprotonated to give an oxonium-annulenium dication. Charge delocalization modes and tropicity in the resulting species are evaluated by NMR and GIAO-DFT. Facile formation of 2 from I in quenching experiments indicates that thermal closing can be achieved with the diprotonated dinitrile, without imposing skeletal rearrangement.
• The Effect of Addition of Fluorescent Moieties to Dihydropyrenes:  Enhancing Photochromicity and Fluorescence Monitoring
  作者：Reginald H. Mitchell、Cornelia Bohne、Stephen G. Robinson、Yanhong Yang

  DOI：10.1021/jo0712392

  日期：2007.10.1

  A series of dihydropyrenes with appending fluorescent moieties were synthesized with the objective of increasing the photochromic efficiency for this class of compounds and to establish how suitable fluorescence would be to follow their photochromic behavior. The ring opening quantum yields of dihydropyrenes with aroyl substituents at the 4-position showed increased ring opening quantum yields without a decrease of the half-life for the thermal reversion of the less stable open isomer, the metacyclophanediene to the dihydropyrene. The fluorescence of the appending naphthoyl or pyrenoyl moieties was not suitable to follow the photochromic cycling of the dihydropyrenes. However, the emission detected above 600 nm of the closed isomer of the dihydropyrene moiety was shown to be a good monitoring method for the photochromic cycling.