(3R,4R)-4-(but-2-ynyloxy)hexa-1,5-dien-3-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R)-4-(but-2-ynyloxy)hexa-1,5-dien-3-ol
• 英文别名: (3R,4R)-4-but-2-ynoxyhexa-1,5-dien-3-ol
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: KHGUTBSHOYTLJO-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-(but-2-ynyloxy)hexa-1,5-dien-3-ol 在 Grubbs catalyst first generation 、 苯酚 作用下， 以 甲苯 为溶剂， 以94%的产率得到(2R,3R)-5-(prop-1-en-2-yl)-2-vinyl-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Ring-Size-Selective Enyne Metathesis as a Tool for Desymmetrization of an EnantiopureC₂-Symmetric Building Block

  摘要：

  The enantiomerically pure C-2-syrnmetrical hexa-1,5-diene-3,4-diol is selectively monopropargylated. The products undergo ring-closing enyne metathesis to give exclusively dihydropyrans as single stereoisomers. An unprotected hydroxy group is identified as the factor controlling the ring-size selectivity.

  DOI：

  10.1021/jo9018649
• 作为产物：
  描述：

  (3R,4R)-1,5-hexadiene-3,4-diol 、 1-溴-2-丁炔 在 四丁基碘化铵 、 sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 、 mineral oil 、 水 为溶剂， 以61%的产率得到(3R,4R)-4-(but-2-ynyloxy)hexa-1,5-dien-3-ol
  参考文献：
  名称：

  Ring-Size-Selective Enyne Metathesis as a Tool for Desymmetrization of an EnantiopureC₂-Symmetric Building Block

  摘要：

  The enantiomerically pure C-2-syrnmetrical hexa-1,5-diene-3,4-diol is selectively monopropargylated. The products undergo ring-closing enyne metathesis to give exclusively dihydropyrans as single stereoisomers. An unprotected hydroxy group is identified as the factor controlling the ring-size selectivity.

  DOI：

  10.1021/jo9018649

文献信息

• The catalytic performance of Ru–NHC alkylidene complexes: PCy₃ versus pyridine as the dissociating ligand
  作者：Stefan Krehl、Diana Geißler、Sylvia Hauke、Oliver Kunz、Lucia Staude、Bernd Schmidt

  DOI：10.3762/bjoc.6.136

  日期：——

  The catalytic performance of NHC-ligated Ru-indenylidene or benzylidene complexes bearing a tricyclohexylphosphine or a pyridine ligand in ring closing metathesis (RCM), cross metathesis, and ring closing enyne metathesis (RCEYM) reactions is compared. While the PCy₃ complexes perform significantly better in RCM and RCEYM reactions than the pyridine complex, all catalysts show similar activity in cross metathesis reactions.

  NHC配体的Ru-茚基亚甲基或苄基亚甲基配合物，在环闭合甲基转移（RCM）、交叉甲基转移和环闭合炔烯甲基转移（RCEYM）反应中的催化性能进行了比较。尽管PCy3配合物在RCM和RCEYM反应中表现明显优于吡啶配合物，但所有催化剂在交叉甲基转移反应中显示出类似的活性。
• Ring-Size-Selective Enyne Metathesis as a Tool for Desymmetrization of an Enantiopure<i>C</i>₂-Symmetric Building Block
  作者：Bernd Schmidt、Lucia Staude

  DOI：10.1021/jo9018649

  日期：2009.12.4

  The enantiomerically pure C-2-syrnmetrical hexa-1,5-diene-3,4-diol is selectively monopropargylated. The products undergo ring-closing enyne metathesis to give exclusively dihydropyrans as single stereoisomers. An unprotected hydroxy group is identified as the factor controlling the ring-size selectivity.