3-Methyl-2-(7-chloro-5-heptynyl)-5-<(Z)-2-methyl-2-carbomethoxy-1-propenyl>furan | 154873-97-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Methyl-2-(7-chloro-5-heptynyl)-5-<(Z)-2-methyl-2-carbomethoxy-1-propenyl>furan
• 英文别名: methyl (Z)-3-[5-(7-chlorohept-5-ynyl)-4-methylfuran-2-yl]-2-methylprop-2-enoate
• CAS: 154873-97-9
• 化学式: C₁₇H₂₁ClO₃
• 分子量: 308.805
• InChiKey: ZBBKXBJUUAHKIX-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-2-(7-chloro-5-heptynyl)-5-<(Z)-2-methyl-2-carbomethoxy-1-propenyl>furan 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到3-Methyl-2-(7-chloro-5-heptynyl)-5-<(Z)-2-methyl-3-hydroxy-1-propenyl>furan
  参考文献：
  名称：

  Synthesis of the pseudopterane 2,5-furanocyclic ring system by [2,3] Wittig ring contraction of bridged furan and dihydrofuran propargylic ethers

  摘要：

  Two routes to the 2,5-furanocyclic ring system of the pseudopterane family of natural products are described. Both employ [2,3] Wittig ring contraction of a 15-membered allylic propargylic ether as the key step. The first route utilizes the bridged 2,5-dihydro furanocyclic ether 24 as the immediate precursor. Treatment with BuLi in THF-pentanes at -78 degrees C affords a 70:30 mixture of trans,anti and trans,syn diastereomers 29 and 31 in 68% yield. The acetate derivatives 30 and 32 are dehydrogenated to furan 33 by MnO2 in ether. In the second route, the furano bridged (Z)-allylic propargylic ether 40Z rearranges to furanocycle 41 in 73% yield upon treatment with LiTMP in; THF-pentane at -78 degrees C.

  DOI：

  10.1021/jo00081a009
• 作为产物：
  描述：

  3-Methyl-2-(7-hydroxy-5-heptynyl)furan 在 2,6-二甲基吡啶 、 18-冠醚-6 、 叔丁基锂 、 双(三甲基硅烷基)氨基钾 、 甲基磺酰氯 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 为溶剂， 反应 9.0h， 生成 3-Methyl-2-(7-chloro-5-heptynyl)-5-<(Z)-2-methyl-2-carbomethoxy-1-propenyl>furan
  参考文献：
  名称：

  Synthesis of the pseudopterane 2,5-furanocyclic ring system by [2,3] Wittig ring contraction of bridged furan and dihydrofuran propargylic ethers

  摘要：

  Two routes to the 2,5-furanocyclic ring system of the pseudopterane family of natural products are described. Both employ [2,3] Wittig ring contraction of a 15-membered allylic propargylic ether as the key step. The first route utilizes the bridged 2,5-dihydro furanocyclic ether 24 as the immediate precursor. Treatment with BuLi in THF-pentanes at -78 degrees C affords a 70:30 mixture of trans,anti and trans,syn diastereomers 29 and 31 in 68% yield. The acetate derivatives 30 and 32 are dehydrogenated to furan 33 by MnO2 in ether. In the second route, the furano bridged (Z)-allylic propargylic ether 40Z rearranges to furanocycle 41 in 73% yield upon treatment with LiTMP in; THF-pentane at -78 degrees C.

  DOI：

  10.1021/jo00081a009