(Z,2S)-5-[5-[[(E)-4-(1-ethoxyethoxy)-2-methylbut-2-enoxy]methyl]-4-methylfuran-2-yl]-2-(methoxymethoxy)-4-methylpent-4-enal | 851760-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Z,2S)-5-[5-[[(E)-4-(1-ethoxyethoxy)-2-methylbut-2-enoxy]methyl]-4-methylfuran-2-yl]-2-(methoxymethoxy)-4-methylpent-4-enal
• CAS: 851760-85-5
• 化学式: C₂₃H₃₆O₇
• 分子量: 424.535
• InChiKey: RQQATEYTWAOPOL-SWSVLKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z,2S)-5-[5-[[(E)-4-(1-ethoxyethoxy)-2-methylbut-2-enoxy]methyl]-4-methylfuran-2-yl]-2-(methoxymethoxy)-4-methylpent-4-enal 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-Butyl-((Z)-(S)-5-{5-[(E)-4-(1-ethoxy-ethoxy)-2-methyl-but-2-enyloxymethyl]-4-methyl-furan-2-yl}-1-ethynyl-2-methoxymethoxy-4-methyl-pent-4-enyloxy)-dimethyl-silane
  参考文献：
  名称：

  Studies toward the Synthesis of Furanocembrane Bipinnatin J: Synthesis of a 2,3,5-Trisubstituted Furfuryl Ether Intermediate

  摘要：

  Synthesis of 2,3,5-trisubstituted furfuryl ether (29), a potential intermediate in a synthetic approach to bipinnatin J, was achieved by a combination of etherification and Stille cross-coupling reaction. Unexpectedly, an intramolecular coupling reaction of 29 proceeded through S(N)2' substitution to give 15-membered furfuryl ether (30). Formation of gamma-butenolide (34) was also accomplished by a ruthenium-catalyzed carbonylation of allenic alcohol (33).

  DOI：

  10.3987/com-04-10317
• 作为产物：
  描述：

  2-methyl-5-bromo-furfurylcarbinol 在 tris(dibenzylideneacetone)dipalladium (0) 三苯胂 、 四丁基氟化铵 、 三氧化硫吡啶 、 2,4-滴二甲胺盐 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (Z,2S)-5-[5-[[(E)-4-(1-ethoxyethoxy)-2-methylbut-2-enoxy]methyl]-4-methylfuran-2-yl]-2-(methoxymethoxy)-4-methylpent-4-enal
  参考文献：
  名称：

  Studies toward the Synthesis of Furanocembrane Bipinnatin J: Synthesis of a 2,3,5-Trisubstituted Furfuryl Ether Intermediate

  摘要：

  Synthesis of 2,3,5-trisubstituted furfuryl ether (29), a potential intermediate in a synthetic approach to bipinnatin J, was achieved by a combination of etherification and Stille cross-coupling reaction. Unexpectedly, an intramolecular coupling reaction of 29 proceeded through S(N)2' substitution to give 15-membered furfuryl ether (30). Formation of gamma-butenolide (34) was also accomplished by a ruthenium-catalyzed carbonylation of allenic alcohol (33).

  DOI：

  10.3987/com-04-10317

文献信息

• Studies toward the Synthesis of Furanocembrane Bipinnatin J: Synthesis of a 2,3,5-Trisubstituted Furfuryl Ether Intermediate
  作者：Masayoshi Tsubuki、Kazunori Takahashi、Ken Sakata、Toshio Honda

  DOI：10.3987/com-04-10317

  日期：——

  Synthesis of 2,3,5-trisubstituted furfuryl ether (29), a potential intermediate in a synthetic approach to bipinnatin J, was achieved by a combination of etherification and Stille cross-coupling reaction. Unexpectedly, an intramolecular coupling reaction of 29 proceeded through S(N)2' substitution to give 15-membered furfuryl ether (30). Formation of gamma-butenolide (34) was also accomplished by a ruthenium-catalyzed carbonylation of allenic alcohol (33).