(Z)-1,8-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methyloct-6-en-4-yn-3-ol | 154874-03-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-1,8-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methyloct-6-en-4-yn-3-ol
• CAS: 154874-03-0
• 化学式: C₂₁H₄₂O₃Si₂
• 分子量: 398.734
• InChiKey: PLOAYTMNYKSTTC-JXAWBTAJSA-N

物化性质

• 沸点：
  428.1±45.0 °C(predicted)
• 密度：
  0.918±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1,8-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methyloct-6-en-4-yn-3-ol 在 4-甲基苯磺酸吡啶 作用下， 生成 (Z)-6-Methoxymethoxy-3-methyl-oct-2-en-4-yne-1,8-diol
  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-(叔丁基-二甲基-硅烷基OXY)-丙醛 、 以79%的产率得到(Z)-1,8-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methyloct-6-en-4-yn-3-ol
  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

文献信息

• Synthesis of the pseudopterane 2,5-furanocyclic ring system by [2,3] Wittig ring contraction of bridged furan and dihydrofuran propargylic ethers
  作者：James A. Marshall、Byung-chan Yu

  DOI：10.1021/jo00081a009

  日期：1994.1

  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.