dodec-6-yn-5-ol | 109271-52-5

• 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: dodec-6-yn-5-ol
• CAS: 109271-52-5
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: AFCFJRHFODEYHF-UHFFFAOYSA-N

物化性质

• 熔点：
  18.8°C (estimate)
• 沸点：
  285.73°C (rough estimate)
• 密度：
  0.8530 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  dodec-6-yn-5-ol 在 三氟化硼乙醚 、 重水 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 5-<(2)H>-dodec-6-yne
  参考文献：
  名称：

  Substituted 4-(1′,2′-alkadienesulphinyl)-morpholines; preparation and hydrolytic desulphinylation into the corresponding alkynes

  摘要：

  DOI：

  10.1016/s0040-4039(01)80555-4
• 作为产物：
  描述：

  正戊醛 、 1-庚炔 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 dodec-6-yn-5-ol
  参考文献：
  名称：

  Studies on Pd(II)-Catalyzed Synthesis of (Z)-α-Haloalkylidene-β-lactones from Cyclocarbonylation of 2-Alkynols and the Subsequent Coupling Reactions

  摘要：

  A good regio- and stereoselectivity was observed for the PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 affording (Z)-alpha-chloroalkylidene-beta-lactons. The highly optically active (Z)-alpha-chloroalkylidene-beta-lactones could be easily prepared from the readily available optically active propargylic alcohols. The Pd(II)-catalyzed cyclocarbonylation of 2-alkynols with CuBr2 was also studied. Although the yields of (Z)-alpha-bromoalkylidene-beta-lactones were low, due to the relatively higher activity of the C-Br bond, the coupling reactions of (Z)-alpha-bromoalkylidene-beta-lactones were quite smooth to afford the corresponding products in high yields. A rationale for this reaction is discussed.

  DOI：

  10.1021/jo0480038

文献信息

• Oxygenation of alkynes to α,β-acetylenic ketones with dioxygen catalyzed by N-hydroxyphthalimide combined with a transition metal
  作者：Satoshi Sakaguchi、Tomoyuki Takase、Takahiro Iwahama、Yasutaka Ishii

  DOI：10.1039/a804956d

  日期：——

  Alkynes were successfully converted into α,β-acetylenic carbonyl compounds through radical-catalyzed aerobic oxidation using N-hydroxyphthalimide (NHPI) combined with a transion metal under mild conditions.

  通过温和条件下的自由基催化有氧氧化反应，利用N-羟基邻苯二甲酰亚胺（NHPI）与过渡金属的组合，成功将炔烃转化为α,β-炔基羰基化合物。
• Saluzzo, Christine; Spina, Anna-Maria La; Picq, Dominique, Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 831 - 843
  作者：Saluzzo, Christine、Spina, Anna-Maria La、Picq, Dominique、Alvernhe, Gerard、Anker, Daniel、et al.

  DOI：——

  日期：——
• Baudin Jean-Bernard; Julia, Sylvestre A; Wang, Yuan, Bulletin de la Societe Chimique de France, 1995, vol. 132, # 7, p. 739 - 753
  作者：Baudin Jean-Bernard、Julia, Sylvestre A、Wang, Yuan

  DOI：——

  日期：——
• McComsey, David F.; Reitz, Allen B.; Maryanoff, Cynthia A., Synthetic Communications, 1986, vol. 16, # 12, p. 1535 - 1550
  作者：McComsey, David F.、Reitz, Allen B.、Maryanoff, Cynthia A.、Maryanoff, Bruce E.

  DOI：——

  日期：——
• Mild and Efficient Synthesis of (<i>Z</i>)-α-Chloroalkylidene-β-lactones via the PdCl₂-Catalyzed Cyclocarbonylation of 2-Alkynols
  作者：Shengming Ma、Bin Wu、Shimin Zhao

  DOI：10.1021/ol0357245

  日期：2003.11.1

  A mild and efficient methodology involving PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 for the synthesis of (Z)-alpha-chloroalkylidene-beta-lactones was developed. Using the readily available optically active propargylic alcohols allows convenient synthesis of the corresponding (Z)-alpha-chloroalkylidene-beta-lactones with high ee values. cis-Chloropalladation was observed as the major pathway, which is unique as compared to the reported data.