2-(3-methyl-n-butanoyl)cyclopentanone | 2570-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-methyl-n-butanoyl)cyclopentanone
• 英文别名: 2-Isovaleroyl-cyclopentan-1-on；2-Isovaleryl-cyclopentanon；2-(3-Methylbutanoyl)cyclopentan-1-one；2-(3-methylbutanoyl)cyclopentan-1-one
• CAS: 2570-71-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: JXHAGPWNUCDUAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-(3-methyl-n-butanoyl)cyclopentanone 在 sodium hydroxide 作用下， 反应 1.0h， 生成 6-Oxo-8-methyl-nonansaeure
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Alkyl-Perhydroazepines from [5,3,0]-Bicyclic Lactams

  摘要：

  The synthesis and utility of a novel class of [5,3,0]-bicyclic lactams are described. Produced by the cyclodehydration of (R)-phenylglycinol with omega -keto acids, lactams 4-6 were obtained as separable diastereomeric mixtures (similar to2:1) in low yields (similar to 40%). Higher chemical yield (up to 61%) was realized tia an alternate route involving ring closure metathesis of 2-allyl-N-acroyl oxazolidines, 8. Stereoselective reductions of the syn-bicyclic lactams, 4a and 5a, occurred with the use of alane or lithiumaluminum hydride, affording azepine alcohols, 11a and;15a, of the R configuration at the 2-position, in good to moderate yields (50-88%). High selectivity was also observed in the diisobutylaluminum hydride reduction of the epimeric anti lactams, 4b and 5b, affording azepine alcohols, 11b and 15b, of the S configuration at C-2. Hydrogenolytic cleavage of the N-benzyl moiety afforded chiral 2-substituted perhydroazepines, (R)- and (S)-12, in good yields and good enantiomeric excesses (84-94%).

  DOI：

  10.1021/jo001548r
• 作为产物：
  描述：

  异戊酰氯 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 101.0h， 生成 2-(3-methyl-n-butanoyl)cyclopentanone
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Alkyl-Perhydroazepines from [5,3,0]-Bicyclic Lactams

  摘要：

  The synthesis and utility of a novel class of [5,3,0]-bicyclic lactams are described. Produced by the cyclodehydration of (R)-phenylglycinol with omega -keto acids, lactams 4-6 were obtained as separable diastereomeric mixtures (similar to2:1) in low yields (similar to 40%). Higher chemical yield (up to 61%) was realized tia an alternate route involving ring closure metathesis of 2-allyl-N-acroyl oxazolidines, 8. Stereoselective reductions of the syn-bicyclic lactams, 4a and 5a, occurred with the use of alane or lithiumaluminum hydride, affording azepine alcohols, 11a and;15a, of the R configuration at the 2-position, in good to moderate yields (50-88%). High selectivity was also observed in the diisobutylaluminum hydride reduction of the epimeric anti lactams, 4b and 5b, affording azepine alcohols, 11b and 15b, of the S configuration at C-2. Hydrogenolytic cleavage of the N-benzyl moiety afforded chiral 2-substituted perhydroazepines, (R)- and (S)-12, in good yields and good enantiomeric excesses (84-94%).

  DOI：

  10.1021/jo001548r

文献信息

• Catalytic Highly Enantioselective Direct Amination of 1,3-Diketones
  作者：Karl Anker Jørgensen、Mauro Marigo、Nagaswamy Kumaragurubaran

  DOI：10.1055/s-2005-861796

  日期：——

  The direct asymmetric amination of 1,3-diketones by azodicarboxylates catalyzed by chiral copper(II) bisoxazolines is presented. Screening of chiral bisoxazoline ligands, Lewis acids, solvents, and other reaction parameters led to an enantioselective direct amination in the 2-position of 1,3-diketones and the optically active functionalized molecules were obtained in high yields and enantioselectivities

  介绍了手性铜 (II) 双恶唑啉催化偶氮二羧酸盐对 1,3-二酮的直接不对称胺化。通过筛选手性双恶唑啉配体、路易斯酸、溶剂和其他反应参数，可以在 1,3-二酮的 2 位进行对映选择性直接胺化，并以高产率和对映选择性获得光学活性官能化分子。
• Formation of δ-Lactones by Cerium-Catalyzed, Baeyer–Villiger-Type Coupling of β-Oxoesters, Enol Acetates, and Dioxygen
  作者：Irina Geibel、Anna Dierks、Marc Schmidtmann、Jens Christoffers

  DOI：10.1021/acs.joc.6b01441

  日期：2016.9.2

  Formation of δ-lactones is observed when cyclopentanone-2-carboxylates are converted in a cerium-catalyzed reaction with α-aryl vinyl acetates under oxidative conditions. The products of this transformation possess a 1,4-dicarbonyl constitution together with a quaternary carbon center. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points

  当环戊酮-2-羧酸酯在铈催化下与α-芳基乙酸乙烯酯在氧化条件下转化为铈时，可观察到δ-内酯的形成。该转化的产物具有1，4-二羰基结构以及季碳中心。大气中的氧气是该过程中的氧化剂，从经济和生态角度来看，这可以认为是理想的氧化剂。这种新的C–C偶联和氧化反应的其他优点是操作简便以及无毒廉价的CeCl 3 ·7 H 2的应用O作为前催化剂。提出了迄今为止前所未有的反应，它是通过1,2-二恶烷衍生物进行的，该衍生物在Baeyer-Villiger型途径中的氧碳正离子形成时分解。这种机理的观点得到了以下观察结果的支持：富电子的（供体取代的或杂芳族的）烯醇酯比缺电子的同类物具有更高的产率。除了作为副产物形成的1,4-二酮和α-羟基化的β-氧代酯外，δ-内酯的收率范围从中等到良（最高74％）。
• Synthesis of 2-Substituted 1,3-Cycloheptanedione via a Lewis Acid Mediated Ring Expansion Reaction
  作者：Kohei Inomata、Yasuyuki Endo

  DOI：10.3987/com-13-s(s)55

  日期：——

  We have established a new route to provide 2-substituted 1,3-cycloheptanediones via a Lewis acid mediated ring expansion reaction of cyclobutanones as the key step. The ring expansion reactions were mediated by a series of Lewis acids. Among the used Lewis acids, ZnI2 was the most practical mediator. This route has succeeded in providing the title compounds even on a multi-gram scale. During the research, the Baeyer-Villiger oxidation of the cyclobutanones to obtain the new bicyclic lactones was also examined. The regioselective oxidation was observed in the case of chlorinated cyclobutanones.
• Blaha,L. et al., Collection of Czechoslovak Chemical Communications, 1965, vol. 30, p. 1214 - 1220
  作者：Blaha,L. et al.

  DOI：——

  日期：——
• Asymmetric Synthesis of 2-Alkyl-Perhydroazepines from [5,3,0]-Bicyclic Lactams
  作者：A. I. Meyers、Susan V. Downing、Michael J. Weiser

  DOI：10.1021/jo001548r

  日期：2001.2.1

  The synthesis and utility of a novel class of [5,3,0]-bicyclic lactams are described. Produced by the cyclodehydration of (R)-phenylglycinol with omega -keto acids, lactams 4-6 were obtained as separable diastereomeric mixtures (similar to2:1) in low yields (similar to 40%). Higher chemical yield (up to 61%) was realized tia an alternate route involving ring closure metathesis of 2-allyl-N-acroyl oxazolidines, 8. Stereoselective reductions of the syn-bicyclic lactams, 4a and 5a, occurred with the use of alane or lithiumaluminum hydride, affording azepine alcohols, 11a and;15a, of the R configuration at the 2-position, in good to moderate yields (50-88%). High selectivity was also observed in the diisobutylaluminum hydride reduction of the epimeric anti lactams, 4b and 5b, affording azepine alcohols, 11b and 15b, of the S configuration at C-2. Hydrogenolytic cleavage of the N-benzyl moiety afforded chiral 2-substituted perhydroazepines, (R)- and (S)-12, in good yields and good enantiomeric excesses (84-94%).