methyl (E)-3-[(3R)-6-oxohex-1-en-3-yl]oxyprop-2-enoate | 1240505-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (E)-3-[(3R)-6-oxohex-1-en-3-yl]oxyprop-2-enoate
• CAS: 1240505-07-0
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: YIKSIDZLHQLYMG-ORZBULNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[(3R)-6-oxohex-1-en-3-yl]oxyprop-2-enoate 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到methyl 2-[(2R,3S,6R)-6-ethenyl-3-hydroxyoxan-2-yl]acetate
  参考文献：
  名称：

  Stereoselective formal synthesis of aspergillide A

  摘要：

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.013
• 作为产物：
  描述：

  methyl (E)-3-[(1R)-1-(3-hydroxypropyl)-2-propenyl]oxy-2-propenoate 在 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 以78%的产率得到methyl (E)-3-[(3R)-6-oxohex-1-en-3-yl]oxyprop-2-enoate
  参考文献：
  名称：

  Stereoselective formal synthesis of aspergillide A

  摘要：

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.013

文献信息

• Stereoselective formal synthesis of aspergillide A
  作者：Gowravaram Sabitha、D. Vasudeva Reddy、A. Senkara Rao、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.06.013

  日期：2010.8

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.