β-valerolactone | 15890-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: β-valerolactone
• 英文别名: 4-ethyloxetan-2-one；(S)-4-methyl-β-butyrolactone；Racemic beta-valerolactone
• CAS: 15890-55-8
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: QTWLQDVFHKLZRA-UHFFFAOYSA-N

物化性质

• 沸点：
  152.7±9.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-valerolactone 生成 4-ethylpropiolactone
  参考文献：
  名称：

  HUFFER, MANFRED;SCHREIER, PETER, FRESENIUS Z. ANAL. CHEM., 333,(1989) N, C. 736-737

  摘要：

  DOI：
• 作为产物：
  描述：

  (RS)-carbonyl(cyclopentadienyl)[(RS)-3-hydroxypentanoyl](triphenylphosphino)iron 在 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以90%的产率得到β-valerolactone
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydrolipstatin and valilactone

  摘要：

  The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(eta(5)-C5H5)Fe(CO)(PPh3)] and beta-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to beta-substituted and alpha,beta-disubstituted beta-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetra hydrolipstatin and valilactone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.012

文献信息

• Succinic anhydrides from epoxides
  申请人：Coates Geoffrey W.

  公开号：US08481756B1

  公开（公告）日：2013-07-09

  Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

  揭示了用于环氧化物的双羰基化的催化剂和方法。每个环氧化物分子与两个一氧化碳分子反应，产生琥珀酸酐。该反应由将Lewis酸性物种与过渡金属羰基络合物结合的催化剂促进。通过使用反应条件，使得两种羰基化反应在无需分离或纯化第一次羰基化产物的情况下在单个过程中实现双羰基化。
• Asymmetric [2 + 2] cycloaddition of ketene with aldehydes catalysed by chiral bissulfonamide–trialkylaluminium complexes
  作者：Yasufumi Tamai、Hideki Yoshiwara、Masahiro Someya、Jun Fukumoto、Sotaro Miyano

  DOI：10.1039/c39940002281

  日期：——

  Asymmetric [2 + 2] cycloaddition of ketene with the aldehydes 1a–g, catalysed by 10 mol% of C2-symmetric bissulfonamide 2a–c–R3Al complexes afforded optically active 4-substituted oxetan-2-ones 3a–g in up to 74% enantiomeric excess.

  C2对称性双磺酰胺2a-c-R3Al络合物催化剂用量为10 mol%时，实现了与醛1a-g的不对称[2+2]环加成反应，合成了光学活性的4-取代氧杂环丁烷-2-酮3a-g，其对映体过量率高达74%。
• Cationic palladium(ii) complex-catalyzed [2 + 2] cycloaddition and tandem cycloaddition–allylic rearrangement of ketene with aldehydes: an improved synthesis of sorbic acid
  作者：Tetsutaro Hattori、Yutaka Suzuki、Osamu Uesugi、Shuichi Oi、Sotaro Miyano

  DOI：10.1039/a908709e

  日期：——

  Cationic palladium(II) complexes [PdL2(PhCN)2](BF4)2 efficiently catalyze the [2 + 2] cycloaddition of ketene with aldehydes to give the corresponding oxetan-2-ones, among which 4-vinyl-substituted ones are further isomerized under the conditions to give 3,6-dihydro-2H-pyran-2-ones in good yields.

  阳离子钯(II)配合物[PdL2(PhCN)2](BF4)2有效催化烯酮与醛的[2 + 2]环加成反应生成相应的oxetan-2-ones，其中4-乙烯基取代的更进一步条件下异构化，以良好的收率得到 3,6-二氢-2H-吡喃-2-酮。
• Practical β-Lactone Synthesis:  Epoxide Carbonylation at 1 atm
  作者：John W. Kramer、Emil B. Lobkovsky、Geoffrey W. Coates

  DOI：10.1021/ol061292x

  日期：2006.8.1

  text] A readily prepared bimetallic catalyst is capable of effecting epoxide carbonylation to produce beta-lactones at substantially lower CO pressures than previously reported catalyst systems. A functionally diverse array of beta-lactones is produced in excellent yields at CO pressures as low as 1 atm. This procedure allows for epoxide carbonylation on a multigram scale without the requirement of specialized

  [反应：见正文]易于制备的双金属催化剂能够在比以前报道的催化剂体系低得多的CO压力下进行环氧化物羰基化反应以生成β-内酯。在低至1 atm的CO压力下，以优异的收率生产出功能多样的β-内酯。该方法允许在数克规模上进行环氧羰基化，而无需专门的高压设备。
• 2-Substituted-6-methyl-1,3-dioxan-4-one
  申请人：Imperial Chemical Industries PLC

  公开号：US04835294A1

  公开（公告）日：1989-05-30

  Novel substituted dioxanones obtained from (R)-3-hydroxybutyric acid, for example 2,2-dimethoxy-6-methyl-1,3-dioxan-4-one, a method for their preparation and processes using the dioxanones as starting material. The dioxanones can be used in particular as intermediates in the preparation of (S)-4-methyl-.beta.-butyrolactone.

  从（R）-3-羟基丁酸获得的替代二氧杂环己酮，例如2,2-二甲氧基-6-甲基-1,3-二氧杂环己-4-酮，以及它们的制备方法和使用二氧杂环己酮作为起始材料的过程。这些二氧杂环己酮可以特别用作（S）-4-甲基-β-丁内酯的制备中间体。