(S)-(-)-5-butyl-δ-valerolactone | 109061-96-3

• 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: (S)-(-)-5-butyl-δ-valerolactone
• 英文别名: S-(-)-5-nonyl-δ-valerolactone；(S)-6-n-butyltetrahydropyran-2-one；(S)-6-butyltetrahydropyran-2-one；nonan-5-olide；(S)-6-Butyltetrahydro-2H-pyran-2-one；(6S)-6-butyloxan-2-one
• CAS: 109061-96-3
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: PXRBWNLUQYZAAX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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

• 作为反应物：
  描述：

  (S)-(-)-5-butyl-δ-valerolactone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以94%的产率得到S-(+)-5-hydroxy-1-nonanol
  参考文献：
  名称：

  Optical Resolution of 5-Alkyl-δ-Valerolactones and Synthesis of Optically Active 5-Fluoroalkanols

  摘要：

  Optical resolutions of 5-alkyl-delta-valerolactones were carried out by derivatization to the diastereomeric amides, in which (R)-(+)1-(1-naphthyl)ethylamine or (S)-(-)-1-phenylethylamine were used as resolving agents. Optically active 5-fluoroalkanols, useful intermediates for fluorinated ferroelectric liquid crystals, were derived from the resolved lactones in four steps without racemization.

  DOI：

  10.1080/10242430210707
• 作为产物：
  描述：

  丁基环氧乙烷 在 palladium on activated charcoal 、 Lindlar's catalyst 吡啶 、 喹啉 、 4-二甲氨基吡啶 、 sodium hydroxide 、 正丁基锂 、 三氟化硼乙醚 、 水 、 氢气 、 trimethoxonium tetrafluoroborate 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 27.25h， 生成 (S)-(-)-5-butyl-δ-valerolactone
  参考文献：
  名称：

  Enzyme assisted synthesis of enantiomerically pure δ-lactones

  摘要：

  Both enantiomeric series of a wide variety of optically pure 6-alkylated delta-lactones - saturated as well as unsaturated - were prepared via an enzyme mediated route. The key reaction step is the nucleophilic ring opening of enantiomerically pure alkyl-oxiranes, accessible via the corresponding beta-hydroxythioethers which can be obtained enantiomerically pure via enzyme catalyzed kinetic resolutions.

  DOI：

  10.1016/s0957-4166(00)80146-9

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。
• Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the CC double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones
  作者：Ji Liu、Jinchuan Wu、Zhi Li

  DOI：10.1039/c4cc04150j

  日期：——

  Enoyl-ACP reductase (FabI) was identified as a non-OYE 'ene'-reductase for asymmetric reduction of the C=C double bond of alpha, beta-unsaturated ketones. Reduction of several 2-alkylidenecyclopentanones with A-FabI and E-FabI gave (R)-2-alkylcyclopentanones in 95-90% and 70-81% ee, respectively. The product ee was improved to 99-98% in high yield by subsequent one-pot biooxidation.

  烯丙基ACP还原酶（FabI）被鉴定为非OYE'烯'还原酶，用于不对称还原α，β-不饱和酮的C = C双键。用A-FabI和E-FabI还原几种2-亚烷基环戊酮，分别得到95-90％和70-81％ee的（R）-2-烷基环戊酮。通过随后的一锅式生物氧化，产物ee以高产率提高至99-98％。
• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.
  作者：Masayuki SATO、Satoshi SUNAMI、Yoshiaki SUGITA、Chikara KANEKO

  DOI：10.1248/cpb.42.839

  日期：——

  A novel enantioselective synthesis of 1, 3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1, 3-dioxin-4-one with achiral aldehydes.

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。
• Gadnon, Rene; Grogan, Gideon; Levitt, Melissa S., Journal of the Chemical Society. Perkin transactions I, 1994, # 18, p. 2537 - 2544
  作者：Gadnon, Rene、Grogan, Gideon、Levitt, Melissa S.、Roberts, Stanley M.、Wan, Peter W. H.、Willetts, Andrew J.

  DOI：——

  日期：——
• Enantio- and Regioselective Baeyer−Villiger Oxidations of 2- and 3-Substituted Cyclopentanones Using Engineered Bakers' Yeast
  作者：Margaret M. Kayser、Gang Chen、Jon D. Stewart

  DOI：10.1021/jo980737v

  日期：1998.10.1