(S)-6-n-propyltetrahydropyran-2-one | 108943-46-0

• 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: (S)-6-n-propyltetrahydropyran-2-one
• 英文别名: (6S)-propyltetrahydropyranone；(S)-6-propyltetrahydro-2H-pyran-2-one；(6S)-6-propyloxan-2-one
• CAS: 108943-46-0
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: FYTRVXSHONWYNE-ZETCQYMHSA-N

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：

  (S)-6-n-propyltetrahydropyran-2-one 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
  参考文献：
  名称：

  Synthesis and Properties of Ferroelectric Liquid Crystals Derived from 5-Alkyl-δ-Valerolactones

  摘要：

  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.

  DOI：

  10.1080/10587250008023865
• 作为产物：
  描述：

  5-氧代戊酸甲酯 在 Ra-Ni sodium hydroxide 、 氢气 、 双氧水 、 对甲苯磺酸 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 10.0h， 生成 (S)-6-n-propyltetrahydropyran-2-one
  参考文献：
  名称：

  A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B-allyldiisopinocampheylborane

  摘要：

  Asymmetric allylboration of aldehydes containing an adjacent ester group with B-allyldiisopinocampheylborane, followed by hydrolysis and cyclization, provides the corresponding allyl substituted lactones in high yields and greater than or equal to 92% enantiomeric excess. Hydrogenation of these lactones provides the corresponding propyl substituted lactones without any loss of optical purity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00477-7

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。
• Regio- and enantioselective remote dioxygenation of internal alkenes
  作者：Xiaonan Li、Tilong Yang、Jiayuan Li、Xiang Li、Pinhong Chen、Zhenyang Lin、Guosheng Liu

  DOI：10.1038/s41557-023-01192-3

  日期：2023.6

  internal alkenes. Here we report a palladium-catalysed highly regio- and enantioselective remote 1,n-dioxygenation (n ≥ 4) of internal alkenes with engineered pyridine-oxazoline (Pyox) ligands. The reactions proceed efficiently and exhibit a broad substrate scope with excellent regio- and enantioselectivity, affording optically pure 1,n-diol acetates as the key synthons for important bioactive molecules

  内部烯烃的对映选择性直接氧化方法为化学家提供了多功能和强大的工具箱，用于合成光学纯醇，这是最特殊的结构基序之一。然而，区域选择性仍然是内部烯烃功能化的一个巨大挑战。在这里，我们报告了钯催化的高度区域选择性和对映选择性远程 1，n-双氧化（n≥4  ）内部烯烃与工程吡啶-恶唑啉 (Pyox) 配体。反应高效进行并表现出广泛的底物范围，具有出色的区域选择性和对映选择性，提供光学纯 1, n-二醇乙酸酯作为重要生物活性分子的关键合成子。实验研究和密度泛函理论计算提供的证据表明，区域选择性受两个烯丙基 C-H 键的反应性差异控制，其中氧钯化是可逆的，第一个钯迁移步骤被证明是区域选择性决定步骤，通过修改苯基取代的 Pyox 配体。
• 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%.
• 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