2-bromo-1-penten-3-ol | 148457-00-5

• 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-penten-3-ol
• 英文别名: 2-bromopent-1-en-3-ol；2-bromo-pent-1-en-3-ol；2-Brom-pent-1-en-3-ol
• CAS: 148457-00-5
• 化学式: C₅H₉BrO
• 分子量: 165.03
• InChiKey: VNWQRPUMHOIEFD-UHFFFAOYSA-N

物化性质

• 沸点：
  165-166 °C(Press: 765 Torr)
• 密度：
  1.351 g/cm3(Temp: 15.5 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-1-penten-3-ol 以92%的产率得到
  参考文献：
  名称：

  Marshall James A., DuBay William J., J. Org. Chem., 58 (1993) N 12, S 3435-3443

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基乙炔基甲醇 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83%的产率得到2-bromo-1-penten-3-ol
  参考文献：
  名称：

  Synthesis of furans by base-catalyzed cyclization-isomerization of .beta.- and .gamma.-alkynyl allylic alcohols

  摘要：

  Beta- and gamma-alkylyl allylic alcohols 3, 13, 26, available through Pd-mediated coupling of appropriate vinylic halides and terminal alkynes, cyclize and subsequently isomerize to furans 4, 17, and 32 upon treatment with KO-t-Bu in t-BuOH-THF at 25-60-degrees-C. The methodology has been used to prepare 2,3-, 2,4-, and 2,3,5-substituted furans. Reactions in t-BuOD as cosolvent lead to deuterium incorporation consistent with concurrent pathways in which direct 5-exo-dig or 5-endo-dig cyclization of the alkynyl allylic alcohol competes with prior isomerization to an allene intermediate which subsequently cyclizes by 5-exo- or 5-endo-dig pathways.

  DOI：

  10.1021/jo00064a038

文献信息

• Lespieau, Annales de Chimie (Cachan, France), 1912, vol. <8>27, p. 169
  作者：Lespieau

  DOI：——

  日期：——
• 1-Bromo-1-lithioethene:  A Practical Reagent for the Efficient Preparation of 2-Bromo-1-alken-3-ols
  作者：Yehor Y. Novikov、Paul Sampson

  DOI：10.1021/ol034594x

  日期：2003.6.1

  A reliable preparative-scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -105 degreesC to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Efficient diastereoselective addition to alpha-siloxy and alpha-methylcyclohexanones, as well as protected 3-keto furanose sugars, is achieved in the presence of 10 mol % CeBr3. The resulting bromoallylic alcohol adducts have considerable potential as synthetic building blocks.
• Lespieau, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911, vol. 152, p. 879
  作者：Lespieau

  DOI：——

  日期：——