2-isopropyl pyrene | 78751-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-isopropyl pyrene
• 英文别名: 2-isopropyl-pyrene；2-isopropylpyrene；Pyrene, 2-(1-methylethyl)-；2-propan-2-ylpyrene
• CAS: 78751-61-8
• 化学式: C₁₉H₁₆
• 分子量: 244.336
• InChiKey: MZHWYYWPJIVLRW-UHFFFAOYSA-N

物化性质

• 沸点：
  396.7±9.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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-isopropyl pyrene 在 氟磺酸 作用下， 以 liquid sulphur dioxide 为溶剂， 生成
  参考文献：
  名称：

  Protonation and sulfinylation of isomeric isopropylpyrenes, 2,7-di-tert-butylpyrene, and tetracyclohexyl- and tetracyclopentylpyrenes: remarkably stable, sterically crowded pyrenium cations

  摘要：

  1-Isopropyl- (1), 2-isopropyl- (2), 4-isopropyl- (3), 1,3,6,8-tetraisopropyl- (4), and 1,3,5,7,9-pentaisopropylpyrene (5), 2,7-di-tert-butylpyrene (6), and 1,3,5,8-tetracyclohexyl- (7) and 2,4,7,9-tetracyclopentylpyrene (8) in FSO3H or CF3SO3H (TfOH) in SO2 or SO2ClF solvent gave stable monopyrenium ions. In agreement with theory, exclusive alpha protonation occurred at low temperature (-75 --> -65-degrees-C) irrespective of the position of the substituents. The position of alpha-protonation is controlled by inductive stabilization of the alkyl (cycloalkyl) groups. Unlike hexahydropyrene which is diprotonated in FSO3H.SbF5 (1:1) Magic acid, with isopropylpyrenes stable dications could not be generated; in SO2 solvent the Wheland intermediates of sulfinylation were observed, whereas in SO2ClF solvent oxidation and monoprotonation were competitive. Charge distribution patterns in the sulfinylation sigma-complexes are similar to those of protonated pyrenium ions. Stable pyrenium cations deprotonate or desulfinylate on quenching without dealkylation or disproportionation. At higher temperatures (ca. -40-degrees-C), ipso-protonated 4 undergoes isomerization in FSO3H/SO2 solvent; other alkyl (cycloalkyl)pyrenium cations show no isomerization/disproportionation. Upon standing in Magic Acid, hexahydropyrene is oxidized to pyrene.

  DOI：

  10.1021/jo00024a018
• 作为产物：
  描述：

  4,5,9,10-四氢芘 在 aluminum (III) chloride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二硫化碳 为溶剂， 反应 87.0h， 生成 2-isopropyl pyrene
  参考文献：
  名称：

  2-取代pyr衍生支架的合成与结构

  摘要：

  y具有形成荧光准分子的倾向，因此这种发色团通常存在于传感器和荧光探针中。2-官能化pyr特别令人感兴趣，但是这些支架的制备并非易事，涉及需要4,5,9,10-四氢py作为关键中间体的合成途径。在此，描述了开发和优化合成2-官能化的-衍生结构单元的途径的方法，该方法具有用作制备荧光探针的标签的潜力。另外，4,5,9,10-四氢-2-py-5-氧戊酸乙酯和2-乙酰基-4,5,9,10-四氢py乙酯的晶体结构揭示了饱和的四氢py环的独特构象。

  DOI：

  10.1016/j.tetlet.2017.10.058

文献信息

• METHOD FOR PRODUCING ARENE COMPOUNDS AND ARENE COMPOUNDS PRODUCED BY THE SAME
  申请人：JSI Silicone Co.

  公开号：US20210188739A1

  公开（公告）日：2021-06-24

  Provided is a method for producing (alkyl)arene compounds represented by Formulae 3-1, 3-2, and 3-3 by the Friedel-Crafts alkylation reaction of alkyl halide compounds and arene compounds using organic phosphine compounds as a catalyst.

  提供了一种通过使用有机膦化合物作为催化剂，通过烷基卤化物化合物和芳烃化合物进行弗里德尔-克拉夫茨烷基化反应生产代表为Formulae 3-1、3-2和3-3的(烷基)芳烃化合物的方法。
• 一种铁催化苄位叔碳断键氧化合成芳酮的方法
  申请人：南京师范大学

  公开号：CN115010584A

  公开（公告）日：2022-09-06

  本发明公开了一种铁催化苄位叔碳断键氧化合成芳酮的方法，以有机溶剂和水溶液为溶剂，在氧化剂的作用下，催化氧化苄位叔碳合成芳酮，反应通式表示如下。本发明使用廉价绿色的铁催化剂，在绿色氧化剂过氧化氢作用下，以乙腈和水为溶剂，将苄位叔碳断键氧化成羰基生成相应的芳酮。本发明催化氧化反应制备芳酮的方法，使用环境友好的廉价金属催化剂和氧化剂，而且反应底物廉价易得性质稳定，具有较好的官能团相容性。在优化的反应条件之下，目标产品分离收率高达96％。
• Berg, Arne; Lam, Joergen; Hansen, Poul Erik, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 8, p. 665 - 677
  作者：Berg, Arne、Lam, Joergen、Hansen, Poul Erik

  DOI：——

  日期：——
• Nitration of isopropylpyrenes. Strained models for protonation and transfer-nitration in the condensed phase
  作者：Kenneth Khosrow Laali、Tze Ming Liang、Poul Erik Hansen

  DOI：10.1021/jo00035a022

  日期：1992.4

  Protic mono- and dinitration of 1,3,5,7,9-pentaisopropylpyrene (1) occurred at the available alpha positions to give 2 and 3. Despite steric crowding, 2 and 3 did not exhibit a torsional barrier to i-Pr rotation at ambient temperatures; however, buttressing of the peri i-Pr groups was evident (H-1 NMR, UV, and force field energy minimizations). Persistent (dihydroxyiminium)pyrenium dications 2a+2 and 3a+2 were formed by low temperature protonation of 2 and 3 with CF3SO3H (TfOH)/SO2 or with FSO3H/SO2. Intramolecular cyclization of the nitro group of 2a+2 gave the rearranged pyrenium ion 2c+. 1 reacted with NO2+BF4- in acetonitrile solvent to give two pyrenium ions stable at rt, viz. the Wheland intermediate of alpha-nitration 2b+2 and the (dihydroxyiminium)pyrenium dication 2a+2; the latter was also the predominant pyrenium ion formed in the reaction of 1 with NO+BF4- in acetonitrile. Reaction of 1 with NO2+BF4- in chloroform solvent gave alpha-nitration products and a persistent radical cation RC. The simultaneous presence of alpha-nitration products and a persistent pyrenium RC was also observed in the reaction of 1 with NO+BF4- in chloroform, where broader NMR line widths and a stronger ESR signal suggested more extensive oxidation. Protic and aprotic nitrations of 1,3,6,8-tetraisopropylpyrene (10) occurred at the alpha-beta positions; a minor addition product (26) was also found. A mixture of isomeric dinitropyrenes was obtained in NO2+ nitration of 1-isopropylpyrene (13). In line with low temperature protonation studies, aprotic nitrations of 2-isopropyl- and 4-isopropylpyrenes occurred predominantly at the alpha positions. The crowded pyrenium ion of 3 and 2 transfer nitrate to aromatics (toluene, mesitylene, benzene) under mild conditions in competition with a more facile transalkylation.
• BERG A.; LAM J.; HANSEN P. E., ACTA CHEM. SCAND., 40,(1986) N 8, 665-677
  作者：BERG A.、 LAM J.、 HANSEN P. E.

  DOI：——

  日期：——

表征谱图