2-Bromo-1-heptene-3,7-diol | 155261-43-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2-Bromo-1-heptene-3,7-diol
• 英文别名: 6-Bromohept-6-ene-1,5-diol
• CAS: 155261-43-1
• 化学式: C₇H₁₃BrO₂
• 分子量: 209.083
• InChiKey: BHRLSPBYAHQQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-1-heptene-3,7-diol 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 二氯甲烷 、 三乙胺 为溶剂， 反应 2.33h， 生成 5-Hydroxy-6-methylene-11-(tetrahydropyranyloxy)-7-undecynyl pivalate
  参考文献：
  名称：

  Synthesis of the Pseudopterane and Furanocembrane Ring Systems by Intraannular Cyclization of .beta.- and .gamma.-Alkynyl Allylic Alcohols

  摘要：

  The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a ''furan last'' approach. The former was obtained in 64% yield upon treatment of the 12-membered beta-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH. The latter was formed in 88% yield from the 14-membered gamma-alkynyl allylic alcohol 25 under comparable conditions. The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horner-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.

  DOI：

  10.1021/jo00086a018
• 作为产物：
  描述：

  1-庚炔-3,7-二醇 在 四乙基溴化铵 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到2-Bromo-1-heptene-3,7-diol
  参考文献：
  名称：

  Synthesis of the Pseudopterane and Furanocembrane Ring Systems by Intraannular Cyclization of .beta.- and .gamma.-Alkynyl Allylic Alcohols

  摘要：

  The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a ''furan last'' approach. The former was obtained in 64% yield upon treatment of the 12-membered beta-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH. The latter was formed in 88% yield from the 14-membered gamma-alkynyl allylic alcohol 25 under comparable conditions. The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horner-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.

  DOI：

  10.1021/jo00086a018

文献信息

• Synthesis of the Pseudopterane and Furanocembrane Ring Systems by Intraannular Cyclization of .beta.- and .gamma.-Alkynyl Allylic Alcohols
  作者：James A. Marshall、William J. DuBay

  DOI：10.1021/jo00086a018

  日期：1994.4

  The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a ''furan last'' approach. The former was obtained in 64% yield upon treatment of the 12-membered beta-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH. The latter was formed in 88% yield from the 14-membered gamma-alkynyl allylic alcohol 25 under comparable conditions. The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horner-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.