3,3,7-trimethyl-1-indanone | 99553-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3,3,7-trimethyl-1-indanone
• 英文别名: 3,3,7-trimethyl-2H-inden-1-one
• CAS: 99553-63-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: FYCRPBXTLKDQRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  一氧化碳 、 2-t-butyl-6-methylphenyl triflate 在 palladium(II) trifluoroacetate 、 [1,3-bis(2,4,6-trimethylphenyl)-4,5-dimethyl]imidazolium chloride 、 cesium pivalate 作用下， 以 乙基苯 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以42%的产率得到3,3,7-trimethyl-1-indanone
  参考文献：
  名称：

  NHC Ligand-Enabled, Palladium-Catalyzed Non-Directed C(sp³)–H Carbonylation To Access Indanone Cores

  摘要：

  A palladium-catalyzed C(sp(3))-H carbonylation of alkylated aryl triflates or bromides under 1 atm of CO has been developed, in which no directing group or oxidant was required. The essence of this reaction is the combination of appropriate NHC ligands with palladium to facilitate the formation of the five-membered cyclopalladium intermediate. Mechanism studies suggest that the insertion of carbon monoxide into two five-membered cyclopalladium species generated via palladium migration might be the crucial step for this transformation. This method offers an efficient solution for expedient construction of indanone cores, which are valuable synthons and pharmacophores ubiquitously found in numerous natural products.

  DOI：

  10.1021/acscatal.9b03426

文献信息

• Arylpyran Pseudoacid Racemization: Rate Estimation and Structural Influences
  作者：Jonathan Fung、Truc-Vi Duong、Keean C. A. Braceros、Marilyn L. Brooks、Katie Schloesser-Lingscheit、Tristen K. S. Tagawa、Johanna M. Wilson、Kevin K. Jones、Edward J. Valente

  DOI：10.1007/s10870-020-00829-2

  日期：2021.3

  frustrated by aryl substituent rearrangement upon ring closure to the intermediate indanones. Structures of rearranged 3-hydroxy-4-methyl-4-(2′-chloro-5′-methylphenyl)isobenzopyran-1-one (pseudoacid) and N-benzyl-6-isopropyl-4,4,8-trimethylisobenzopyrimidin-1-one (pseudoamide) are reported. Graphic Abstract Arylpyran pseudoacids undergo slow ring opening and fast ring closing in solution amounting to racemization

  摘要 芳基吡喃假酸在相当于外消旋化的过程中对氧代羧酸显示出缓慢的开环和对内酯（假酸）的快速闭环。所研究的化合物在“Cooper's Pseudoacid”[3-羟基-4,4-二甲基异苯并吡喃-1-one, 1 ] 上形成图案，通过空间压缩对其进行修饰以影响外消旋化速率。d 6 -DMSO 中的假酸 1 对外消旋化的屏障 (ΔH ‡ ) 为 +77.8(3) kJ/mol，通过在 25 °C 至 100 °C 下测得的动态核磁共振谱线展宽及其非对映宝石的聚结确定-二甲基信号在 78.5 °C。1 在室温下的溶液半衰期是几秒钟。各种芳基 5-取代基的引入导致 5-氟-8-甲基衍生物类似的外消旋化障碍，5-甲基-8-甲基、5-氯-8-甲基和5-溴-7-甲基衍生物的壁垒越来越高。在 3-羟基-4,4,5,8-四甲基异苯并吡喃-1-one 中，屏障为 + 104(6) kJ/mol，室温下的溶液对映异构体
• 6-Alkylindan-1-one als Riechstoffe
  申请人：HAARMANN & REIMER GMBH

  公开号：EP1310240A1

  公开（公告）日：2003-05-14

  Die Erfindung betrifft die Verwendung von 6-Alkylindan-1-onen als Riechstoffe, ein Verfahren zu ihrer Herstellung, Riechstoffmischungen enthaltend 6-Alkylindan-1-one sowie parfümierte Produkte enthaltend 6-Alkylindan-1-one.

  本发明涉及 6-烷基茚满-1-酮作为香水的用途、其制备工艺、含有 6-烷基茚满-1-酮的香水混合物以及含有 6-烷基茚满-1-酮的香水产品。
• NHC Ligand-Enabled, Palladium-Catalyzed Non-Directed C(sp³)–H Carbonylation To Access Indanone Cores
  作者：Shou-Le Cai、Yan Li、Chi Yang、Jie Sheng、Xi-Sheng Wang

  DOI：10.1021/acscatal.9b03426

  日期：2019.11.1

  A palladium-catalyzed C(sp(3))-H carbonylation of alkylated aryl triflates or bromides under 1 atm of CO has been developed, in which no directing group or oxidant was required. The essence of this reaction is the combination of appropriate NHC ligands with palladium to facilitate the formation of the five-membered cyclopalladium intermediate. Mechanism studies suggest that the insertion of carbon monoxide into two five-membered cyclopalladium species generated via palladium migration might be the crucial step for this transformation. This method offers an efficient solution for expedient construction of indanone cores, which are valuable synthons and pharmacophores ubiquitously found in numerous natural products.