(4R,5R)-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone | 105015-53-0

• 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: (4R,5R)-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone
• 英文别名: (4R,5R)-5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone；(4R,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one；(4R,5R)-5-n-butyl-4-methyl-dihydrofuran-2-one；cis-4-n-butyl-3-methyl-γ-butyrolactone；5-butyl-4-methyldihydro-2(3H)-furanone；5-butyl-4-methyldihydrofuran-2(3H)-one；cis-3-Methyl-4-octanolide；(4R,5R)-5-butyl-4-methyloxolan-2-one
• CAS: 105015-53-0
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: WNVCMFHPRIBNCW-HTQZYQBOSA-N

物化性质

• 沸点：
  246.5±8.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)
• 保留指数：
  1286

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-methyl-5-butyl-2(5H)furanone 生成 (4R,5R)-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  WATANABE, MITSUAKI;TSUKAZAKI, MASAO;HIRAKAWA, YOSHIAKI;IWAO, MASATOMO;FUR+, CHEM. AND PHARM. BULL., 37,(1989) N1, C. 2914-2919

  摘要：

  DOI：

文献信息

• A general and concise stereodivergent chiral pool approach toward trans-(4S,5R)- and cis-(4R,5R)-5-alkyl-4-methyl-γ-butyrolactones: Syntheses of (+)-trans- and (+)-cis-whisky and cognac lactones from d-(+)-mannitol
  作者：Avrajit Manna、Ipsita Chakraborty、Sandip Chatterjee、Tanurima Bhaumik

  DOI：10.1016/j.carres.2021.108452

  日期：2021.12

  A straightforward synthesis of (+)-trans-(4S,5R)- and (+)-cis-(4R,5R)-whisky lactones starting from d-(+)-mannitol has been reported here in fewer number of efficient steps compared to existing literature processes involving d-mannitol as the chiral pool starting material. Chiron approach directly translated chirality of d-mannitol to one of the two chiral centers in these target molecules. Toward

  从d -(+)-甘露醇开始直接合成 (+)-反式-(4 S ,5 R )- 和 (+)-顺式-(4 R ,5 R )-威士忌内酯的报道较少与涉及d-甘露醇作为手性池起始材料的现有文献方法相比，有效步骤的数量。Chiron 方法直接将d-甘露醇的手性转化为这些靶分子中的两个手性中心之一。为此，立体异构纯的反式和顺式在倒数第二步中形成碘甲基-γ-内酯。这两种作为通用的高级通用中间体也分别转化为 (+)-反式-(4 S ,5 R )- 和 (+)-顺式-(4 R ,5 R )-干邑内酯。据我们所知，迄今为止还没有报道从d-甘露醇开始合成干邑内酯。所有这些内酯都被确定为陈年酒精饮料的关键香气成分。
• Efficient Remote Axial-to-Central Chirality Transfer in Enantioselective SmI₂-Mediated Reductive Coupling of Aldehydes with Crotonates of Atropisomeric 1-Naphthamides
  作者：Yan Zhang、Yongqiang Wang、Wei-Min Dai

  DOI：10.1021/jo0526486

  日期：2006.3.1

  different 2-substituted 8-methoxy-1-naphthamides. The enantiomers of atropisomeric 8-methoxy-1-naphthamides were prepared through a chemical resolution process, and their absolute stereochemistry was determined by X-ray crystal structural analysis. It was found that the linkage between crotonate and the C2 position of 8-methoxy-1-naphthamides remarkably influenced the efficiency of remote chirality transfer

  在SmI 2介导的醛与具有不同的2-取代的8-甲氧基-1-萘酰胺的巴豆酸酯的还原偶联中，已经研究了通过远程酰胺构象控制对映选择性的方法。通过化学拆分方法制备对映异构体8-对甲氧基-1-萘酰胺的对映异构体，并通过X射线晶体结构分析确定其绝对立体化学。发现巴豆酸酯和8-甲氧基-1-萘酰胺的C2位之间的键合显着影响源自酰胺构象的远程手性转移的效率。在所检查的四种巴豆酸酯中，一种由2-羟基-8-甲氧基-1-萘酰胺衍生的戊烯酸酯与戊醛反应，以使顺式的ee最高，> 99％-γ-丁内酯，合并产率为90％，顺/反比为90:10。我们开发了一种在温和条件下通过C8氧将手性巴豆酸酯连接到Rink酰胺树脂上的新程序，并在固相反应中获得了相同水平的极远的轴向向中心手性转移。
• A simple route to the syntheses of both enantiomers of trans-oak lactone and (+)-cis-oak lactone
  作者：Manju Ghosh、Sritama Bose、Subrata Ghosh

  DOI：10.1016/j.tetlet.2008.07.026

  日期：2008.9

  Stereocontrolled syntheses of both enantiomers of trans-oak lactone and (+)-cis-oak lactone have been achieved from a common precursor.

  反式-橡木内酯和（+）-顺式-橡木内酯的两种对映异构体的立体控制合成都是由一种常见的前体完成的。
• Synthesis of γ-Lactones via the Kowalski Homologation Reaction: Protecting-Group-Free Divergent Total Syntheses of Eupomatilones-2,5,6, and 3-<i>epi</i>-Eupomatilone-6
  作者：Hosam Choi、Hanho Jang、Hyoungsu Kim、Kiyoun Lee

  DOI：10.1021/acs.orglett.9b02848

  日期：2019.10.4

  A highly efficient synthesis of functionalized chiral γ-butyrolactone scaffolds has been described. The basis of the approach is the Kowalski ester homologation that is modified for our proposed transformation. The newly developed methodology combines a divergent synthetic strategy to permit a straightforward protecting-group-free asymmetric total syntheses of eupomatilones-2,5,6, and 3-epi-eupomatilone-6

  已经描述了功能化的手性γ-丁内酯支架的高效合成。该方法的基础是Kowalski酯的同系物，该同系物针对我们提出的转化进行了修改。新开发的方法结合了多样化的合成策略，可从市售原料中分五步或六步直接合成eupomatilones-2、5、6和3 - epi -eupomatilone-6的无保护基的不对称全合成。迄今为止报道的最短的合成方法之一。
• Stereoselective Iodolactonization of 4-Allenoic Acids with Efficient Chirality Transfer: Development of a New Electrophilic Iodination Reagent
  作者：Xiaobing Zhang、Chunling Fu、Yihua Yu、Shengming Ma

  DOI：10.1002/chem.201200229

  日期：2012.10.15

  A highly stereoselective iodolactonization of 4‐allenoic acids with a new sterically demanding electrophilic iodination reagent to afford optically active γ‐butyrolactones has been developed. The reaction shows high efficiency of axial chirality transfer and excellent Z/E selectivity and has been applied to the synthesis of chiral cis‐β,γ‐disubstituted γ‐butyrolactones to give very high diastereomeric

  已经开发了一种高度立体选择性的4-烯丙酸碘代内酯化反应，并使用了一种新的空间上要求亲电的碘化试剂，以提供光学活性的γ-丁内酯。该反应显示出较高的轴向手性转移效率和出色的Z / E选择性，已被用于手性顺-β，γ-二取代的γ-丁内酯的合成，具有非常高的非对映异构体和对映异构体过量值。该反应已成功用于天然化合物（+）-顺式威士忌内酯和（+）-顺式-3-甲基-4-癸内酯的合成中。