(R)-(+)-1-(2-furyl)but-3-ynyl acetate | 924295-39-6

• 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-ynyl acetate
• 英文别名: [(1R)-1-(furan-2-yl)but-3-ynyl] acetate
• CAS: 924295-39-6
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: BEYASEBOZAOVQE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 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-ynyl acetate 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 生成 (R)-(-)-1-(furan-2-yl)but-3-yn-1-ol
  参考文献：
  名称：

  Conformational control on remote stereochemistry in the intramolecular Pauson–Khand reactions of enynes tethered to homoallyl and homopropargyl alcohols

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2006.11.012
• 作为产物：
  描述：

  糠醛 在 zinc/copper couple 、 PS-C Amona II lipase 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (R)-(+)-1-(2-furyl)but-3-ynyl acetate
  参考文献：
  名称：

  经由闭环易位反应的立体选择性合成光学活性二氢呋喃和二氢吡喃

  摘要：

  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。

  DOI：

  10.1016/j.tetasy.2011.07.003

文献信息

• 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.