2H-吡喃-2-酮,6-乙基四氢-,(S)- | 108943-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 2H-吡喃-2-酮,6-乙基四氢-,(S)-
• 英文名称: (S)-(-)-5-ethyl-δ-valerolactone
• 英文别名: (S)-6-ethyl-tetrahydro-pyran-2-one；(S)-[5]heptanolide；S-(-)-5-ethyl-5-hydroxy-valeric acid lactone；2H-Pyran-2-one, 6-ethyltetrahydro-, (6S)-；(6S)-6-ethyloxan-2-one
• CAS: 108943-44-8
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: JFVQYQDTHWLYHG-LURJTMIESA-N

物化性质

• 沸点：
  227.0±8.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  2H-吡喃-2-酮,6-乙基四氢-,(S)- 在 三乙烯二胺 、 lithium aluminium tetrahydride 、 二乙胺基三氟化硫 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-(-)-5-fluoroheptyl benzoate
  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：

  6-乙基四氢-2H-吡喃-2-酮 在 盐酸 作用下， 以 乙醇 、 苯 为溶剂， 生成 2H-吡喃-2-酮,6-乙基四氢-,(S)-
  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

文献信息

• An Enantioselective Synthetic Route to Atractyligenin Using the Oxazaborolidine-Catalyzed Reduction of β-Silyl- or β-Stannyl-Substituted α,β-Enones as a Key Step
  作者：E. J. Corey、Angel Guzman-Perez、Scott E. Lazerwith

  DOI：10.1021/ja973034o

  日期：1997.12.1

  enantioselective synthetic route to the bicyclic tetraene ester 3, a key intermediate for the synthesis of the naturally occurring adenosine diphosphate transport inhibitor atractyligenin (2). The success of this route depended on the extension of the oxazaborolidine-catalyzed (CBS) reduction of an achiral β-stannyl-substituted α,β-enone (6c) to form a chiral allylic alcohol and further steps to effect simultaneous

  在本文中，我们描述了双环四烯酯 3 的新型催化对映选择性合成路线，这是合成天然存在的二磷酸腺苷转运抑制剂苍术 (2) 的关键中间体。该路线的成功取决于恶唑硼烷催化 (CBS) 还原非手性 β-甲锡烷基取代的 α,β-烯酮 (6c) 以形成手性烯丙醇，以及实现手性同时转移的进一步步骤，碳环形成和四元立体中心形成，这导致了三烯酸 13。13 到 3 的转化是通过四步序列有效地进行的，包括碘内酯化、双消除和酯化。结合使用 CBS 减少适当的 α，
• Preparation of vinyl lactones and corresponding Mannich bases
  申请人：Hoffmann-La Roche Inc.

  公开号：US03984427A1

  公开（公告）日：1976-10-05

  Vinyl ketones and Mannich-bases obtained therefrom are useful as intermediates in the total synthesis of steroids having valuable pharmacological properties. These compounds are prepared by the low temperature reaction of a vinyl Grignard e.g., vinyl magnesium chloride with substituted .gamma., .delta. or .epsilon. lactones followed, if desired, by reaction of the vinyl ketone obtained with a primary or secondary amine. Particular compounds prepared by this procedure include 2-(2-substituted aminoethyl)-6-substituted-2-hydroxy-tetrahydropyrans and the tautomers thereof.

  乙烯酮和由此得到的曼尼希碱在合成具有有价值药理特性的类固醇的过程中作为中间体是有用的。这些化合物通过乙烯格氏试剂（例如乙烯镁氯化物）与取代的γ、δ或ε内酯的低温反应制备得到，随后，如果需要，再将得到的乙烯酮与一级或二级胺反应。通过这种方法制备的特定化合物包括2-(2-取代氨基乙基)-6-取代-2-羟基四氢吡喃及其互变异构体。
• Catalytic Asymmetric Synthesis of Alkyl Substituted Lactones by Enantioselective and Chemoselective Alkylation of Formylesters with Dialkylzincs Using<i>N</i>,<i>N</i>-Dibutylnorephedrine
  作者：Kenso Soai、Shuji Yokoyama、Tomoiki Hayasaka、Katsumi Ebihara

  DOI：10.1246/cl.1988.843

  日期：1988.5.5

  Optically active 4-alkyl-γ-butyrolactones and 5-alkyl-δ-valerolactones were obtained in high enantiomeric excesses (85–95% e.e.) from the catalytic asymmetric alkylation of 3- and 4-formylesters with dialkylzincs using N,N-dibutylnorephedrine as catalyst.

  以 N,N-二丁基去甲麻黄碱为催化剂，用二烷基锌催化 3-和 4-甲酸酯与二烷基锌的不对称烷基化反应，获得了光学活性较高的 4-烷基-γ-丁内酯和 5-烷基-δ-戊内酯对映体过量（85-95% e.e.）。
• Synthesis and Properties of Ferroelectric Liquid Crystals Derived from 5-Alkyl-δ-Valerolactones
  作者：Riswoko Asep、Yoshio Aoki、Takuji Hirose、Hiroyuki Nohira

  DOI：10.1080/10587250008023865

  日期：2000.7

  New homologous FLCs (I similar to II-n [n=1 similar to4]) derived from optically active 5-alkyl-6-valerolactones were synthesized. Their mesomorphic properties were systematically investigated with respect to their molecular structures, which were different in terms of the length of an alkyl group attached to a chiral centre and the direction of phenylpyrimidyl group. For compounds type I-n, with pyrimidyl group conjugated to the terminal position carrying chiral 5-fluoro-alkyloxy tail, elongation of the attached alkyl groups enhanced the stability of the chiral smectic C phase, while the other type, with pyrimidyl group conjugated to the terminal position carrying achiral alkyloxy tail, showed no remarkable alteration in the stability of the phase. Short optical response time (22 mus, 80 degreesC[Tc-T=10K]) was found for the FLC II-3 that has almost the same magnitude of spontaneous polarization (25nCcm(-2), 80 degreesC[Tc-T=10K]) with that of 11-4.
• Steroid Total Synthesis, Part II; (?)-17?-Hydroxy-des-A-androst-9-en-5-one
  作者：G. Saucy、R. Borer

  DOI：10.1002/hlca.19710540746

  日期：1971.11.1

  AbstractBased on the results obtained in the racemic series (part I), (—)‐17β‐hydroxy‐des‐A‐androst‐9‐en‐5‐one has been synthesized, starting with (S)‐(—)‐5‐heptanolide. The key step, viz. the condensation of (S)‐(—)‐7‐hydroxy‐1‐nonen‐3‐one (or its amine adduct) with 2‐methyl‐cyclopentane‐1, 3‐dione involves an asymmetric induction. Model experiments with (R)‐(+)‐5‐decanolide leading to the enantiomeric homolog of the BCD‐tricyclic compound are also described.