5-(3Z)-3-hexen-1-yldihydro-2(3H)-furanone | 155682-86-3

• 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: 5-(3Z)-3-hexen-1-yldihydro-2(3H)-furanone
• 英文别名: (R)-(+)-γ-jasmolactone；(R)-γ-jasmolactone；(R)-(+)-jasmolactone；(R)-Z-7-decen-4-olide；2(3H)-Furanone, 5-(3-hexenyl)dihydro-, (R-(Z))-；(5R)-5-[(Z)-hex-3-enyl]oxolan-2-one
• CAS: 155682-86-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: NKNGVPNCSFZRSM-ZBJFTSOASA-N

物化性质

• 沸点：
  279.1±9.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 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：

  4-酮庚二酸 在 sodium tetrahydroborate 、 dimethyl sulfide borane 、 sodium acetate 、 pyridinium chlorochromate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.17h， 生成 5-(3Z)-3-hexen-1-yldihydro-2(3H)-furanone
  参考文献：
  名称：

  Enantioselective synthesis of (−)-γ-jasmolactone

  摘要：

  The title compound was prepared in seven steps starting from the commercially available 4-ketopimelic acid. The key step features an enantioselective lactonization promoted by PPL. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00444-4

文献信息

• Facile Synthesis of Optically Active .GAMMA.-Lactones via Lipase-catalyzed Reaction of 4-Substituted 4-Hydroxybutyramides.
  作者：Yassufumi MATSUMURA、Teruko ENDO、Mituo CHIBA、Hidemichi FUKAWA、Yoshiyasu TERAO

  DOI：10.1248/cpb.48.304

  日期：——

  afford (S)-succinic acid monoester and unreacted (R)-4-hydroxybutyramide derivative, which were separated easily by treatment with an alkaline solution. Both enantiomers were converted easily to optically active gamma-substituted gamma-butyrolactones.

  外消旋的4-取代的4-羟基丁酰胺与琥珀酸酐的脂肪酶催化的酯交换反应对映选择性地进行，得到（S）-琥珀酸单酯和未反应的（R）-4-羟基丁酰胺衍生物，通过用碱溶液处理容易地分离它们。两种对映异构体均易于转化为光学活性的γ-取代的γ-丁内酯。
• Combination of Novozym 435–Catalyzed Hydrolysis and Mitsunobu Reaction for Production of (<i>R</i>)-<font>γ</font>-Lactones
  作者：Yasutaka Shimotori、Tetsuo Miyakoshi

  DOI：10.1080/00397910903134618

  日期：2010.5.11

  Chiral -lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435-catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)--lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435-catalyzed hydrolysis and the Mitsunobu reaction.
• A Short Enantioselective Synthesis of (<i>R</i>)‐(+)‐γ‐Jasmolactone
  作者：Giuliano C. Clososki、Lauri J. Missio、João V. Comasseto

  DOI：10.1081/scc-120039490

  日期：2004.1.1

  (R)-(+)-gamma-Jasmolactone (1b) was synthesized in 92% ee in two steps, starting from the easily prepared (S)-(-)-3-(5-oxo-tetrahydro-furan2-yl)-propionic acid benzyl ester (2). The key step features an inversion of configuration of the stereogenic center.
• Enantioselective synthesis of (−)-γ-jasmolactone
  作者：Lauri.J Missio、J.Valdir Comasseto

  DOI：10.1016/s0957-4166(00)00444-4

  日期：2000.11

  The title compound was prepared in seven steps starting from the commercially available 4-ketopimelic acid. The key step features an enantioselective lactonization promoted by PPL. (C) 2000 Published by Elsevier Science Ltd.