(R)-(+)-5-propyl-δ-valerolactone | 108943-45-9

• 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)-(+)-5-propyl-δ-valerolactone
• 英文别名: (R)-6-n-propyltetrahydropyran-2-one；(R)-(+)-5-octanolide；(6R)-6-propyloxan-2-one
• CAS: 108943-45-9
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: FYTRVXSHONWYNE-SSDOTTSWSA-N

物化性质

• 沸点：
  239.8±8.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)
• LogP：
  1.355 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (R)-(+)-5-propyl-δ-valerolactone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-(-)-5-hydroxyoctanol
  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：

  1,5-辛内酯 在 盐酸 作用下， 以 乙醇 、 苯 为溶剂， 生成 (R)-(+)-5-propyl-δ-valerolactone
  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

• 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。
• Titanocene-Catalyzed Regiodivergent Epoxide Openings
  作者：Andreas Gansäuer、Chun-An Fan、Florian Keller、Jutta Keil

  DOI：10.1021/ja0686211

  日期：2007.3.1

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.
• Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids
  作者：Mario Aquino、Silvia Cardani、Giovanni Fronza、Claudio Fuganti、Rosalino Pulido Fernandez、Auro Tagliani

  DOI：10.1016/s0040-4020(01)81944-x

  日期：1991.9

  gamma- and delta-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3 ,4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid: the delta-lactones were always obtained in an ee% higher than the gamma-lactones and ranging from 70% to 100%.
• Asymmetric reduction of the prochiral carbonyl group of aliphatic .gamma.- and .delta.-keto acids by use of fermenting bakers' yeast
  作者：Masanori Utaka、Hisashi Watabu、Akira Takeda

  DOI：10.1021/jo00228a039

  日期：1987.9
• 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