(3S,4R)-3-[(E,1R)-1-hydroxybut-2-enyl]-4-prop-2-enyloxolan-2-one | 132537-54-3

• 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: (3S,4R)-3-[(E,1R)-1-hydroxybut-2-enyl]-4-prop-2-enyloxolan-2-one
• CAS: 132537-54-3
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: UENCBSLWZQIQKH-ZCPSBMCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-[(E,1R)-1-hydroxybut-2-enyl]-4-prop-2-enyloxolan-2-one 在 sodium periodate 、 碳酸氢钠 、 对甲苯磺酸 、 二乙胺 、 原甲酸三甲酯 作用下， 以 二氯甲烷 、 均三甲苯 为溶剂， 生成 (3aR,7R,9aR)-3a,6,7,9a-Tetrahydro-7-methylspirofuran-5(3H),2'-<1,3>dioxolan>-1(4H)-one
  参考文献：
  名称：

  Enantiospecific synthesis of the the tricyclxc nucleus of acetoxycrenulide by claisen ring exfansion

  摘要：

  DOI：

  10.1016/s0040-4039(00)97221-6
• 作为产物：
  描述：

  (R)-4-allyldihydrofuran-2(3H)-one 在 sodium periodate 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 6.0h， 生成 (3S,4R)-3-[(E,1R)-1-hydroxybut-2-enyl]-4-prop-2-enyloxolan-2-one
  参考文献：
  名称：

  Suitability of the Claisen ring expansion protocol for crenulide diterpene construction

  摘要：

  An enantiospecific synthesis of optically pure 2 a molecule possessing the ring system characteristic of the crenulide diterpenes, is reported. The nine-step sequence began with the previously described R lactone 6. The early bond-forming reactions include an aldol condensation with crotonaldehyde and intramolecular selenonium ion-promoted cyclization with participation by the neighboring hydroxyl group. Selenoxide elimination made possible the acquisition of allyl vinyl ether 4. Thermal activation of the latter in hot mesitylene proceeded via a Claisen ring expansion pathway to give 36a. This key intermediate was then ketalized, subjected to Simmons-Smith cyclopropanation, and carried through a selenoxide elimination step to arrive ultimately at 2. Selected transformations of the medium-ring bicyclic lactones are described, accompanied by X-ray crystallographic studies to substantiate the stereochemical assignments advanced throughout the investigation.

  DOI：

  10.1021/jo00110a053

文献信息

• Enantiospecific synthesis of the the tricyclxc nucleus of acetoxycrenulide by claisen ring exfansion
  作者：Jesus Ezquerra、Wei He、Leo A. Paquette

  DOI：10.1016/s0040-4039(00)97221-6

  日期：1990.1
• EZQUERRA, JESUS;HE, WEI;PAQUETTE, LEO A., TETRAHEDRON LETT., 31,(1990) N8, C. 6979-6982
  作者：EZQUERRA, JESUS、HE, WEI、PAQUETTE, LEO A.

  DOI：——

  日期：——
• Suitability of the Claisen ring expansion protocol for crenulide diterpene construction
  作者：Leo A. Paquette、Jesus Ezquerra、Wei He

  DOI：10.1021/jo00110a053

  日期：1995.3

  An enantiospecific synthesis of optically pure 2 a molecule possessing the ring system characteristic of the crenulide diterpenes, is reported. The nine-step sequence began with the previously described R lactone 6. The early bond-forming reactions include an aldol condensation with crotonaldehyde and intramolecular selenonium ion-promoted cyclization with participation by the neighboring hydroxyl group. Selenoxide elimination made possible the acquisition of allyl vinyl ether 4. Thermal activation of the latter in hot mesitylene proceeded via a Claisen ring expansion pathway to give 36a. This key intermediate was then ketalized, subjected to Simmons-Smith cyclopropanation, and carried through a selenoxide elimination step to arrive ultimately at 2. Selected transformations of the medium-ring bicyclic lactones are described, accompanied by X-ray crystallographic studies to substantiate the stereochemical assignments advanced throughout the investigation.