(R)-(+)-1-(2-furyl)but-3-en-1-yl acetate | 517907-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (R)-(+)-1-(2-furyl)but-3-en-1-yl acetate
• 英文别名: (R)-(+)-1-(furan-2-yl)but-3-enyl acetate；(R)-1-(furan-2-yl)but-3-en-1-yl acetate；(R)-1-(2-furyl)but-3-en-1-yl acetate；[(1R)-1-(furan-2-yl)but-3-enyl] acetate
• CAS: 517907-50-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: QHZMBJOQUONRJX-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-(2-furyl)but-3-en-1-yl acetate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 (R)-1-furan-2-yl-but-3-en-1-ol
  参考文献：
  名称：

  化学酶法合成旋光性杂环​​均烯丙基和均丙炔醇

  摘要：

  已开发出一种化学酶学方法，该方法是在水性介质中使用铟介导的杂环醛的烯丙基化烯丙基化，然后在有机介质中假单胞菌cepcia脂肪酶催化外消旋均烯丙基和均炔丙醇的对映选择性酰化。观察到，与天然酶（PS Amano）相比，固定在陶瓷颗粒上的脂肪酶（PS-C Amano II）以更少的时间以高对映选择性的方式催化拆分。该方法提供了新的功能化手性合成子，可用于合成天然和假天然产物。

  DOI：

  10.1016/s0957-4166(02)00743-7
• 作为产物：
  描述：

  糠醛 在 碘 、 magnesium 、 lipase 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 (R)-(+)-1-(2-furyl)but-3-en-1-yl acetate
  参考文献：
  名称：

  旋光共轭γ-和δ-内酯衍生物的合成及生物学评价

  摘要：

  已经通过闭环易位反应有效地合成了由烯丙基和高烯丙基醇骨架衍生的杂芳基取代的γ-和δ-内酯衍生物的外消旋形式和对映体形式。2-杂芳基取代的烯丙基和高烯丙基醇已通过酶法高效分离，具有高ee（97-99％）和已知的立体化学。评价目标内酯的抗微生物和抗氧化活性。

  DOI：

  10.1016/j.bmcl.2012.07.090

文献信息

• Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction
  作者：Merve Çayir、Sema Demirci、Serdar Sezer、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2011.07.003

  日期：2011.6

  derivatives, respectively, with chemical yields which varied between 72% and 88%. On the other hand, enantiomerically enriched enynes derived from homoallyl and homopropargyl alcohols gave the corresponding optically active dihydropyrans with conjugated diene units with chemical yields between 70% and 80%. A subsequent Diels–Alder reaction of the dihydropyran derivatives with a diene unit with tetracyanoethylene

  描述了二烯的闭环复分解反应和衍生自烯丙基，高烯丙基和高炔丙醇主链的闭环烯炔复分解反应。2-杂芳基取代的烯丙基，高烯丙基和高炔丙基醇可通过高ee（93-99％）的酶促拆分和已知的立体化学方法轻松有效地拆分。衍生自烯丙醇和高烯丙基醇的对映体富集的二烯分别提供相应的对映体富集的二氢呋喃和二氢吡喃衍生物，化学收率在72％至88％之间变化。另一方面，衍生自高烯丙基和高炔丙基醇的对映异构体富集的炔烃得到具有共轭二烯单元的相应的旋光性二氢吡喃，其化学收率在70％至80％之间。
• Dynamic Kinetic Resolution of Homoallylic Alcohols: Application to the Synthesis of Enantiomerically Pure 5,6-Dihydropyran-2-ones and δ-Lactones
  作者：Madeleine C. Warner、Grigory A. Shevchenko、Suzan Jouda、Krisztián Bogár、Jan-E. Bäckvall

  DOI：10.1002/chem.201301980

  日期：2013.10.4

  Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transformed into homoallylic acrylates after hydrolysis of the ester function and subsequent DMAP‐catalyzed esterification with acryloyl chloride. After ring‐closing

  使用南极假丝酵母脂肪酶B和钌催化剂2对各种均烯丙基醇进行动态动力学拆分，可得到高收率和高对映选择性的均烯丙基乙酸酯。酯官能团水解后，这些对映体纯乙酸酯进一步转化为均烯丙基丙烯酸酯，随后通过DMAP催化用丙烯酰氯酯化。开环易位后，获得了5,6-二氢吡喃-2-酮。碳碳双键的选择性加氢可提供相应的δ-内酯，而不会丢失手性信息。
• Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines
  作者：Serdar Sezer、Yasemin Gümrükçü、İrem Bakırcı、M. Yağız Ünver、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2012.04.016

  日期：2012.5

  The intramolecular Pauson-Khand and ring closing metathesis (RCM) reactions of nitrogen containing chiral enynes and dienes are described. The enyne and diene systems comprised of N-propargylated and N-allylated units are constructed on chiral homoallylic or homopropargylic alcohol backbones, respectively, via S(N)2 and/or modified Mitsunobu reactions. The racemic homoallylic and homopropargylic alcohol derivatives were successfully resolved in high ee (93-99%) by applying chemoenzymatic methods using various lipases such as PS-C II, Lipozyme, and CAL-B. Each enantiomerically enriched enyne afforded the most conformationally stable diastereomeric cyclopenta[c]pyridine ring system as the sole product, whereas enantiomerically enriched dienes gave tetrahydropyridine derivatives as a result of intramolecular Pauson-Khand and RCM reactions, respectively. (C) 2012 Elsevier Ltd. All rights reserved.
• Conformational control on remote stereochemistry in the intramolecular Pauson–Khand reactions of enynes tethered to homoallyl and homopropargyl alcohols
  作者：Serdar Sezer、Devrim Özdemirhan、Ertan Şahin、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2006.11.012

  日期：2006.11

  An intramolecular Pauson-Khand reaction of enynes derived from homoallyl and homopropargyl alcohols is described. 2-Furyl substituted homoallyl and homopropargyl alcohols are easily and efficiently resolved through enzymatic resolution in a high ee (93-99%) with a known stereochemistry. Each enantiomerically enriched enyne affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system. (c) 2006 Elsevier Ltd. All rights reserved.