(R)-6-allyl-tetrahydropyran-2-one | 214335-61-2

• 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)-6-allyl-tetrahydropyran-2-one
• 英文别名: 6-allyl-tetrahydropyran-2-one；(6R)-allyltetrahydropyranone；(6R)-6-prop-2-enyloxan-2-one
• CAS: 214335-61-2
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: SPYPESQMARESMP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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)-6-allyl-tetrahydropyran-2-one 在 Ra-Ni 氢气 作用下， 以 水 、 乙酸乙酯 为溶剂， 以90%的产率得到(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
• 作为产物：
  描述：

  5-氧代戊酸甲酯 在 sodium hydroxide 、 双氧水 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 (R)-6-allyl-tetrahydropyran-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

• Convergent Strategy Towards the Synthesis of Restricted Analogues of Peloruside A
  作者：Nicolas Zimmermann、Pierre Pinard、Bertrand Carboni、Pascal Gosselin、Catherine Gaulon-Nourry、Gilles Dujardin、Sylvain Collet、Jacques Lebreton、Monique Mathé-Allainmat

  DOI：10.1002/ejoc.201201728

  日期：2013.4

  A rapid convergent strategy to access unsaturated analogues of peloruside A has been demonstrated. This is depicted as an original C11-C12 aldol connection between a C12-C20 ketone fragment and a C2-C11 pyran fragment bearing an aldehyde function, with high yield and a good level of diastereoselectivity. The desired unsaturated macrocycle was obtained by a late-stage ring closing metathesis reaction

  已经证明了一种获取 peloruside A 的不饱和类似物的快速收敛策略。这被描述为 C12-C20 酮片段和带有醛官能团的 C2-C11 吡喃片段之间的原始 C11-C12 醛醇连接，具有高产率和良好的非对映选择性。通过后期闭环复分解反应获得所需的不饱和大环。
• Stereoselective allylation of aldehydes on solid support and its application in biology-oriented synthesis (BIOS)
  作者：Victor Mamane、Ana B. García、Jayant D. Umarye、Torben Lessmann、Stefan Sommer、Herbert Waldmann

  DOI：10.1016/j.tet.2007.01.041

  日期：2007.6

  allylation of aldehydes on solid support is reported. Different kinds of chiral allylboron reagents with complementary direction of stereoinduction were applied successfully in this reagent-controlled transformation. The homoallylic alcohol products are generated with high levels of stereoselectivity and in high yields. The crotylation of aldehydes on solid support employing (E)- and (Z)-Ipc2crotylborane

  报道了在固体载体上醛的不对称烯丙基化的系统研究。具有立体诱导互补方向的不同种类的手性烯丙基硼试剂已成功应用于该试剂控制的转化中。均丁醇产物以高水平的立体选择性和高产率产生。使用（E）-和（Z）-Ipc 2在固相载体上醛的crotylation。巴豆基硼烷还以很高的立体诱导水平和高收率进行。描述了该方法在通过烯丙基部分的后续修饰来合成化合物集合中的应用。特别地，已经通过包括天然产物的环释放方法合成了γ-和δ-内酯的集合。另外，已经报道了解决固体载体上双键的长期存在问题的方法。我们还证明了以迭代方式在固体载体上应用醛的立体选择性烯丙基化以生成多元醇结构的可行性。
• A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B-allyldiisopinocampheylborane
  作者：P.Veeraraghavan Ramachandran、Marek P. Krzeminski、M.Venkat Ram Reddy†、Herbert C. Brown

  DOI：10.1016/s0957-4166(98)00477-7

  日期：1999.1

  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.