(Z)-2-methyl-6-pentyloct-3-yn-5-ene-2,7-diol

• 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: (Z)-2-methyl-6-pentyloct-3-yn-5-ene-2,7-diol
• 英文别名: (Z)-7-methyl-3-pentyloct-3-en-5-yne-2,7-diol
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: HXJDWPUOSMVUNN-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  6
• 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：

  (Z)-2-methyl-6-pentyloct-3-yn-5-ene-2,7-diol 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以42.6 mg的产率得到2-methyl-5-(2-methylprop-1-enyl)-3-pentylfuran
  参考文献：
  名称：

  Synthesis of Polysubstituted Furans Based on a Stepwise Sonogashira Coupling of (Z)-3-Iodoalk-2-en-1-ols with Terminal Propargylic Alcohols and Subsequent Au(I)- or Pd(II)-Catalyzed Cyclization−Aromatization via Elimination of H₂O

  摘要：

  Recently, we have developed highly regio- and stereoselective carbometalation of 2-alkynols and 2,3-allenols. The organometallacyclic intermediates may be trapped with 12 to afford 3-iodoalk-2-en-1-ols. These 3-iodoalk-2-en-1-ols may readily undergo the Sonogashira coupling with terminal propargyl alcohols to form 4-alkyn-2-ene-1,6-diols. Subsequent cycloisomerization in DMA or CH2Cl2 with Au(PPh3)Cl and AgOTf as the catalyst would afford polysubstituted 2-(1-alkenyl)furans; with PdCl2 as the catalyst and the reaction in DMA in the presence of allylic bromides, the same substrates afforded polysubstituted 2-( 1,4-alkadienyl)furans. In both types of catalyzed cyclization reactions, the elimination of H2O promoted the aromatization to form the furan ring. Different alkyl or aryl groups could be introduced into different positions of furans due to the substituent-loading capability of 3-iodoalkenols and diversity of the terminal propargyl alcohols and allylic bromides.

  DOI：

  10.1021/jo100146p
• 作为产物：
  描述：

  正戊基溴化镁 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 反应 2.0h， 生成 (Z)-2-methyl-6-pentyloct-3-yn-5-ene-2,7-diol
  参考文献：
  名称：

  铜（I）催化的仲末端炔丙醇区域选择性抗碳金属化的研究

  摘要：

  开发了高度区域选择性的Cu（I）催化的仲末端炔丙基醇与提供2个取代的烯丙基醇的1°烷基或芳基格氏试剂的抗碳金属化反应。通过使用该方法，可以从旋光的炔丙醇制备旋光的烯丙醇而对映体纯度没有明显的损失。形成的环状有机金属中间体可以进行碘化反应或Pd（0）催化的偶联反应，得到立体定义的烯丙基醇。

  DOI：

  10.1021/jo0524021

文献信息

• Studies on the Cu(I)-Catalyzed Regioselective <i>anti</i>-Carbometallation of Secondary Terminal Propargylic Alcohols
  作者：Zhan Lu、Shengming Ma

  DOI：10.1021/jo0524021

  日期：2006.3.31

  A highly regioselective Cu(I)-catalyzed anti-carbometallation of secondary terminal propargylic alcohols with 1° alkyl or aryl Grignard reagents affording 2-substituted allylic alcohols was developed. By using this method, optically active allylic alcohols can be prepared from the optically active propargylic alcohols without obvious loss of the enantiopurity. The cyclic organometallic intermediate

  开发了高度区域选择性的Cu（I）催化的仲末端炔丙基醇与提供2个取代的烯丙基醇的1°烷基或芳基格氏试剂的抗碳金属化反应。通过使用该方法，可以从旋光的炔丙醇制备旋光的烯丙醇而对映体纯度没有明显的损失。形成的环状有机金属中间体可以进行碘化反应或Pd（0）催化的偶联反应，得到立体定义的烯丙基醇。
• Synthesis of Polysubstituted Furans Based on a Stepwise Sonogashira Coupling of (Z)-3-Iodoalk-2-en-1-ols with Terminal Propargylic Alcohols and Subsequent Au(I)- or Pd(II)-Catalyzed Cyclization−Aromatization via Elimination of H₂O
  作者：Xiaobing Zhang、Zhan Lu、Chunling Fu、Shengming Ma

  DOI：10.1021/jo100146p

  日期：2010.4.16

  Recently, we have developed highly regio- and stereoselective carbometalation of 2-alkynols and 2,3-allenols. The organometallacyclic intermediates may be trapped with 12 to afford 3-iodoalk-2-en-1-ols. These 3-iodoalk-2-en-1-ols may readily undergo the Sonogashira coupling with terminal propargyl alcohols to form 4-alkyn-2-ene-1,6-diols. Subsequent cycloisomerization in DMA or CH2Cl2 with Au(PPh3)Cl and AgOTf as the catalyst would afford polysubstituted 2-(1-alkenyl)furans; with PdCl2 as the catalyst and the reaction in DMA in the presence of allylic bromides, the same substrates afforded polysubstituted 2-( 1,4-alkadienyl)furans. In both types of catalyzed cyclization reactions, the elimination of H2O promoted the aromatization to form the furan ring. Different alkyl or aryl groups could be introduced into different positions of furans due to the substituent-loading capability of 3-iodoalkenols and diversity of the terminal propargyl alcohols and allylic bromides.