1,3-dimesityl-1H-indene | 133338-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1,3-dimesityl-1H-indene
• 英文别名: 1,3-dimesitylindene；1,3-bis(2,4,6-trimethylphenyl)-1H-indene
• CAS: 133338-93-9
• 化学式: C₂₇H₂₈
• 分子量: 352.519
• InChiKey: QSMASBMGKOFTHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  1H-茚-1,2,3-三酮2-肟 在 磷化氢 、 高氯酸 、 lithium (1 percent sodium) 、 氢碘酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 1,3-dimesityl-1H-indene
  参考文献：
  名称：

  2-Diazo-1,3-dimesityl-2H-indene and 1,3-dimesitylisoindenylidene

  摘要：

  Reduction of 1,3-dihydroxy-1,3-dimesitylindan-2-one oxime 5 with Hl-HOAc gives the primary enamine, 2-amino-1,3-dimesitylindene 7. This resists hydrolysis to 1,3-dimesitylindan-2-one 6 even with boiling concentrated HCl-dioxane (1:1); steric protection of C-3 by the mesityl group and an overwhelming preference for the enamine tautomer may account for the unusual stability of 7. With NaNO2-HOAc 7 gives 2-diazo-1,3-dimesityl-2H-indene 2, the only known 2-diazoindene. The C-13 and N-15 NMR shifts of C-2 and the terminal nitrogen in 2 suggest somewhat greater diazonium indenylide character than for 1-diazoindene. Though isolable, 2 decomposes slowly at 20-degrees-C or upon exposure to visible light to give the hydrocarbons 14, 15 and 16, which probably arise via 1,3-dimesitylisoindenylidene 3 and the o-quinodimethanes 18 and 19. The decomposition of 2 in the presence of oxygen, 4-phenyltriazoline-3,5-dione, and N-phenylmaleimide are described.

  DOI：

  10.1039/p19910000249

文献信息

• Preparation, thermolysis, and photolysis of 2-diazo-1,3-dimesityl-2H-indene: a sterically stabilised 2-diazoindene
  作者：David W. Jones、Alan Pomfret

  DOI：10.1039/c39820000919

  日期：——

  2-Diazo-1,3-dimesityl-2H-indene (2) is prepared by reaction of 2-amino-1,3-dimesityl-2H-indene with sodium nitrite–acetic acid; though isolable (2) decomposes either thermally (20 ° C) or on exposure to visible light to give the hydrocarbons (6), (7), and (8) derived via the carbene (9) and the o-quinodimethane (10).

  2-重氮基1,3-二基2 ħ茚（2）由2-氨基1,3-二基2的反应制备ħ用亚硝酸钠-乙酸-茚; 尽管可分离的（2）在热（20°C）或暴露于可见光下会分解，从而生成通过卡宾（9）和邻喹啉二甲烷（10）衍生出的碳氢化合物（6），（7）和（8）。 。
• Tunable Gold‐catalyzed Reactions of Propargyl Alcohols and Aryl Nucleophiles
  作者：Helgi Freyr Jónsson、Thomas Nordbø Solvi、Sondre Lomeland、Ann Christin Reiersølmoen、Anne Fiksdahl

  DOI：10.1002/open.202200030

  日期：2022.5

  alcohols with aryl nucleophiles were studied. Highly selective and tunable synthetic methods were developed for one-pot formation of either triaryl-allenes, diaryl-indenes or tetraaryl-allyl target products by appropriate reaction conditions (time, temperature, catalyst, substrate, nucleophile, solvent). Corresponding 2-halo-indenes, appropriate for further Pd-catalyzed reactions, were also obtained

  研究了 1,3-二芳基炔丙醇与芳基亲核试剂的可调谐金 (III) 催化转化。通过适当的反应条件（时间、温度、催化剂、底物、亲核试剂、溶剂），开发了高选择性和可调节的合成方法，用于一锅形成三芳基-丙二烯、二芳基-茚或四芳基-烯丙基目标产物。在 NXS (X=Br, I) 的存在下，也以一锅法获得了适用于进一步 Pd 催化反应的相应 2-卤代茚。
• JONES, D. W.;POMFRET, A., J. CHEM. SOC. CHEM. COMMUN., 1982, N 16, 919-921
  作者：JONES, D. W.、POMFRET, A.

  DOI：——

  日期：——
• 2-Diazo-1,3-dimesityl-2H-indene and 1,3-dimesitylisoindenylidene
  作者：David W. Jones、Alan Pomfret

  DOI：10.1039/p19910000249

  日期：——

  Reduction of 1,3-dihydroxy-1,3-dimesitylindan-2-one oxime 5 with Hl-HOAc gives the primary enamine, 2-amino-1,3-dimesitylindene 7. This resists hydrolysis to 1,3-dimesitylindan-2-one 6 even with boiling concentrated HCl-dioxane (1:1); steric protection of C-3 by the mesityl group and an overwhelming preference for the enamine tautomer may account for the unusual stability of 7. With NaNO2-HOAc 7 gives 2-diazo-1,3-dimesityl-2H-indene 2, the only known 2-diazoindene. The C-13 and N-15 NMR shifts of C-2 and the terminal nitrogen in 2 suggest somewhat greater diazonium indenylide character than for 1-diazoindene. Though isolable, 2 decomposes slowly at 20-degrees-C or upon exposure to visible light to give the hydrocarbons 14, 15 and 16, which probably arise via 1,3-dimesitylisoindenylidene 3 and the o-quinodimethanes 18 and 19. The decomposition of 2 in the presence of oxygen, 4-phenyltriazoline-3,5-dione, and N-phenylmaleimide are described.