(6S)-(+)-jasmine lactone | 136173-91-6

• 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: (6S)-(+)-jasmine lactone
• 英文别名: (S)-(+)-jasmine lactone；(+)-(6S)-Tetrahydro-6-((Z)-pent-2-enyl)-2H-pyran-2-one；(6S)-6-[(Z)-pent-2-enyl]oxan-2-one
• CAS: 136173-91-6
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: XPPALVZZCMPTIV-ZBJFTSOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-7-癸烯-5-酸 在 盐酸 、 sodium hydroxide 、 (1R,2S)-2-氨基-1,2-二苯基乙醇 作用下， 反应 1.33h， 生成 (6S)-(+)-jasmine lactone
  参考文献：
  名称：

  Optical Resolution of Fragrant Lactones

  摘要：

  Optical resolution of six chiral fragrant lactones (delta-jasmine lactone, massoia lactone, tuberolactone, pentynyllactone, delta-decalactone, and gamma-nonalactone) was investigated by means of either the diastereomeric salt formation method or the diastereomeric amide formation method. Using these procedures, we obtained each enantiomer from five of the six lactones, except for massoia lactone. All five lactones were obtained in a good yield and with high optical purity. Sensoric characteristics on both enantiomers and racemic modification of four lactones are given.

  DOI：

  10.3987/com-99-s149

文献信息

• The first asymmetric total synthesis of (R)-tuberolactone, (S)-jasmine lactone and (R)-δ-decalactone
  作者：Gowravaram Sabitha、V. Bhaskar、J.S. Yadav

  DOI：10.1016/j.tetlet.2006.08.135

  日期：2006.11

  A general synthetic approach has been developed for the first asymmetric total synthesis of tuberolactone 1, jasmine lactone 2 and δ-decalactone 3. The key step is the selective hydrogenation of triple and endocyclic double bonds in the key intermediate 4.

  已开发出一种通用的合成方法，用于首次不对称的全合成内酯1，茉莉内酯2和δ-十内酯3。关键步骤是在关键中间体4中对三键和内环双键进行选择性加氢。
• Synth�se des (?)-(6R)-et(+)-(6S)-t�trahydro-6-[(Z)-pent-2-�nyl]-2H-pyran-2-one, lactones deJasminum grandiflorum L. et dePolianthes tuberosa L.
  作者：Florian Blaser、Pierre-Fran�ois Deschenaux、Thomas Kallimopoulos、Andr� Jacot-Guillarmod

  DOI：10.1002/hlca.19910740412

  日期：1991.6.19

  Synthesis of (−)-(6R)- and (+)-(6S)-Tetrahydro-6-[(Z)-pent-2-enyl]-2H-Pyran-2-one, lactones from Jasminum grandiflorum L. and from Polianthes tuberosa L.

  茉莉（Jasminum grandiflorum）的合成（-）-（6 R）-和（+）-（6 S）-四氢-6-[（Z）-戊-2-烯基] -2 H-吡喃-2-酮L.和来自Polianthes tuberosa L.
• Optical Resolution of Fragrant Lactones
  作者：Hiroyuki Nohira、Keiko Mizuguchi、Toru Murata、Yuko Yazaki、Miho Kanazawa、Yoshio Aoki、Misako Nohira

  DOI：10.3987/com-99-s149

  日期：——

  Optical resolution of six chiral fragrant lactones (delta-jasmine lactone, massoia lactone, tuberolactone, pentynyllactone, delta-decalactone, and gamma-nonalactone) was investigated by means of either the diastereomeric salt formation method or the diastereomeric amide formation method. Using these procedures, we obtained each enantiomer from five of the six lactones, except for massoia lactone. All five lactones were obtained in a good yield and with high optical purity. Sensoric characteristics on both enantiomers and racemic modification of four lactones are given.