2-Methyl-2-(3-methylbutyl)-1,3-cyclopentanedione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-2-(3-methylbutyl)-1,3-cyclopentanedione
• 英文别名: 2-Methyl-2-(3-methylbutyl)cyclopentane-1,3-dione
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: COKANOWZJIANMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-2-(3-methylbutyl)-1,3-cyclopentanedione 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-hydroxy-2-isopentyl-2-methylcyclopentan-1-one
  参考文献：
  名称：

  CuH 催化的环状 1,3-二酮的对映选择性去对称化

  摘要：

  在此，我们报告了 CuH 催化的前手性环戊烷-1,3-二酮的不对称去对称化，使用 PMHS 作为廉价的氢化物源，通过氢化硅烷化反应获得具有全碳季中心和高非对映选择性的环状 3-羟基酮。该反应显示出高官能团耐受性，包括具有广泛底物范围的可还原炔烃、烯烃和酯基团。手性环状 3-羟基酮结构单元的重要性也通过 (-)-雌酮、毒柯烯烷 E 核心和稠合吲哚的合成得到证明。

  DOI：

  10.1021/acs.orglett.2c03359
• 作为产物：
  描述：

  二(三甲基硅氧基)环丁烯 、 5-甲基-2-己酮 在 三氟化硼乙醚 作用下， 反应 72.0h， 以65%的产率得到2-Methyl-2-(3-methylbutyl)-1,3-cyclopentanedione
  参考文献：
  名称：

  Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones

  摘要：

  Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.

  DOI：

  10.1021/jo00085a041

文献信息

• Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones
  作者：Tracy J. Jenkins、D. Jean Burnell

  DOI：10.1021/jo00085a041

  日期：1994.3

  Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.
• CuH-Catalyzed Enantioselective Desymmetrization of Cyclic 1,3-Diketones
  作者：Vaibhav B. Patil、Sandip B. Jadhav、Jagadeesh Babu Nanubolu、Rambabu Chegondi

  DOI：10.1021/acs.orglett.2c03359

  日期：2022.11.11

  cyclopentane-1,3-diones to access cyclic 3-hydroxy ketones having an all-carbon quaternary center with high diastereoselectivity via hydrosilylation using PMHS as an inexpensive hydride source. This reaction displays high functional group tolerance including reducible alkyne, alkene, and ester groups with a broad substrate scope. The importance of chiral cyclic 3-hydroxy ketone building blocks was also demonstrated

  在此，我们报告了 CuH 催化的前手性环戊烷-1,3-二酮的不对称去对称化，使用 PMHS 作为廉价的氢化物源，通过氢化硅烷化反应获得具有全碳季中心和高非对映选择性的环状 3-羟基酮。该反应显示出高官能团耐受性，包括具有广泛底物范围的可还原炔烃、烯烃和酯基团。手性环状 3-羟基酮结构单元的重要性也通过 (-)-雌酮、毒柯烯烷 E 核心和稠合吲哚的合成得到证明。