(R)-δ-undecalactone | 108861-12-7

• 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: (R)-δ-undecalactone
• 英文别名: (R)-6-Hexyltetrahydro-2H-pyran-2-one；(6R)-6-hexyloxan-2-one
• CAS: 108861-12-7
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: YZRXRLLRSPQHDK-SNVBAGLBSA-N

物化性质

• 沸点：
  291.9±0.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)
• LogP：
  2.949 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  sodium methylate 、 (R)-δ-undecalactone 以 甲醇 为溶剂， 以62%的产率得到(R)-6-hexyl-4-methoxy-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  A facile enzyme assisted route to enantiomerically pure δ - lactones

  摘要：

  Enantiomerically pure 1,2-epoxyalkanes, obtained via enzymatic resolution of suitable precursors can serve as key building blocks for the preparation of the title compounds. Using a simple and very short synthetic protocol enantiomerically pure delta-lactones are obtained in high yields.

  DOI：

  10.1016/s0957-4166(00)82176-x
• 作为产物：
  描述：

  (R)-5-hydroxy-N-methylundecanamide 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 27.0h， 生成 (R)-δ-undecalactone
  参考文献：
  名称：

  Enantioselective Synthesis of δ-Lactones with Lipase-Catalyzed Resolution and Mitsunobu Reaction

  摘要：

  Both enantiomers of a series of delta-lactones (e.g., delta-decalactone, delta-dodelactone, and delta-hexadecalactone) were synthesized stereoselectively by Novozym 435-catalyzed resolution. Furthermore, only (S)-enantiomers of delta-lactones were synthesized with a combination of Novozym 435-catalyzed resolution and Mitsunobu reaction.

  DOI：

  10.1080/00397911.2010.529230

文献信息

• Stereoselective synthesis of chiral δ-lactones <i>via</i> an engineered carbonyl reductase
  作者：Tao Wang、Xiao-Yan Zhang、Yu-Cong Zheng、Yun-Peng Bai

  DOI：10.1039/d1cc04542c

  日期：——

  A carbonyl reductase variant, SmCRM5, from Serratia marcescens was obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg−1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5 showed a 13.8-fold higher specific activity towards the model substrate

  来自粘质沙雷氏菌的羰基还原酶变体Sm CR M5是通过结构引导的定向进化获得的。该变体对 16 种测试底物中的大多数表现出改善的比活性 (U mg -1 )，并在 13 种 γ-/δ-内酯的不对称合成中提供高达 99% 的高立体选择性。特别是，SmCR M5对模型底物（即5-氧代癸酸）的比活性高出 13.8 倍，并在 99% ee 中产生 ( R )-δ-癸内酯，时空产率 (STY) 为 301 g L -1 d -1. 六种δ-内酯的高收率和高对映体纯度的制备表明这些高附加值化学品的生物催化合成是可行的，为贵金属催化提供了一种具有成本效益的绿色替代品。
• Cascade Biotransformations via Enantioselective Reduction, Oxidation, and Hydrolysis: Preparation of (<i>R</i>)-δ-Lactones from 2-Alkylidenecyclopentanones
  作者：Ji Liu、Zhi Li

  DOI：10.1021/cs400101v

  日期：2013.5.3

  cascade biotransformation involving enantioselective reduction of a C═C double bond, Baeyer–Villiger oxidation, and lactone hydrolysis was developed as a green and sustainable tool for synthesizing enantiopure δ-lactones. One-pot cascade biotransformations were achieved with Acinetobacter sp. RS1 containing a novel enantioselective reductase and an enantioselective lactone hydrolase and Escherichia coli

  作为涉及绿色和可持续的合成对映纯δ-内酯的工具，首次涉及级联生物转化涉及C═C双键的对映选择性还原，Baeyer-Villiger氧化和内酯水解。不动杆菌属一锅级联生物转化。RS1含有新颖的对映选择性还原酶和对映体选择性内酯水解酶和大肠杆菌共表达的环己酮单加氧酶和葡糖脱氢酶，转换容易获得的2- alkylidenecyclopentanones 1 - 2成相应的有价值的香精香料（[R）-δ-内酯5 - 6在高ee中。一锅法合成优于报道的两步法制备。该概念对于开发其他包含C═C双键的底物的氧化还原级联反应很有用。
• A method for the chromatographic resolution of tetrahydropyran-2-ones
  作者：Philip Ashworth、Shiddappa L. Belagali、Sharon Casson、Anna Marczak、Philip Kocieński

  DOI：10.1016/s0040-4020(01)80729-8

  日期：1991.12

  The spirocyclic ortholactones prepared from certain tetrahydropyran-2-ones (valerolactones) and (1R)-1-phenylpropan-1,3-diol are readily separable by flash chromatography on silica gel. Hydrolysis of the resolved ortholactones then provides the pure homochiral lactones.

  由某些四氢吡喃-2-酮（戊内酯）和（1R）-1-苯基丙烷-1,3-二醇制备的螺环原内酯很容易通过硅胶快速色谱分离。然后水解分解的原内酯，得到纯的手性内酯。
• Pd-Catalyzed kinetic resolution of cyclic enol ethers. An enantioselective route to functionalised pyrans
  作者：Jean-Olivier Zirimwabagabo、Joseph P. A. Harrity

  DOI：10.1039/c4cc00109e

  日期：——

  Functionalised cyclic enol ethers can be recovered with high levels of enantiocontrol after an asymmetric catalytic [1,3]-rearrangement reaction.

  通过不对称催化[1,3]-重排反应，可以高度控制环状烯醚的手性，并使其得到回收。
• Methyl Ricinoleate as Platform Chemical for Simultaneous Production of Fine Chemicals and Polymer Precursors
  作者：Antoine Dupé、Mathieu Achard、Cédric Fischmeister、Christian Bruneau

  DOI：10.1002/cssc.201200320

  日期：2012.11

  modification of methyl ricinoleate by etherification of the hydroxyl group was accomplished by using a nonclassical ruthenium‐catalyzed allylation reaction and also by esterification. Methyl ricinoleate derivatives were engaged in ring‐closing metathesis (RCM) reactions leading to biosourced 3,6‐dihydropyran and α,β‐unsaturated lactone derivatives with concomitant production of polymer precursors. Sequential

  通过使用非经典钌催化的烯丙基化反应以及酯化反应，可以通过羟基的醚化改性蓖麻油酸甲酯。蓖麻油酸甲酯衍生物参与闭环复分解（RCM）反应，从而导致生物来源的3,6-二氢吡喃和α，β-不饱和内酯衍生物，并同时产生聚合物前体。顺序RCM /加氢和RCM /交叉复分解也被用作合成四氢吡喃和内酯衍生物以及有价值的单体（即聚酰胺前体）的直接方法。