3-oxabicyclo[16.3.1]docosa-1(22),18,20-trien-16-yn-2-one | 758718-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxabicyclo[16.3.1]docosa-1(22),18,20-trien-16-yn-2-one
• CAS: 758718-81-9
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: NKLXPURAXODBGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-oxabicyclo[16.3.1]docosa-1(22),18,20-trien-16-yn-2-one 在 tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate 三乙氧基硅烷 、 silver fluoride 作用下， 以 二氯甲烷 、 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 3-oxabicyclo[16.3.1]docosa-1(22),16,18,20-tetraen-2-one
  参考文献：
  名称：

  (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne–yne metathesis/semi-reduction

  摘要：

  A concise, practical and stereoselective entry into macrocyclic (E)-alkenes is outlined comprising a sequence of ring closing alkyne metathesis (RCAM), trans-selective hydrosilylation of the resulting cycloalkynes catalyzed by [Cp*Ru(MeCN)(3)]PF6, and a protodesilylation of the ensuing vinylsilanes with AgF in aq. THF/MeOH. Moreover, the first examples of intramolecular enyne-yne metathesis reactions catalyzed by the Schrock alkylidyne complex (tBUO)(3)W drop CCMe3 are reported; the resulting cyclic enynes can be converted along similar lines into the corresponding (E,E)-configured 1,3-dienes in good overall yields. Cycloalkyne 4 and the (E)-configured cyclic olefins 6 and 21 were characterized by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.042
• 作为产物：
  描述：

  3-Prop-1-ynyl-benzoic acid pentadec-13-ynyl ester 在 Tris(t-butoxy)(2,2-dimethylpropylidyne)tungsten(VI), 98% Schrock Alkyne Metathesis Catalyst 作用下， 以 甲苯 为溶剂， 以71%的产率得到3-oxabicyclo[16.3.1]docosa-1(22),18,20-trien-16-yn-2-one
  参考文献：
  名称：

  (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne–yne metathesis/semi-reduction

  摘要：

  A concise, practical and stereoselective entry into macrocyclic (E)-alkenes is outlined comprising a sequence of ring closing alkyne metathesis (RCAM), trans-selective hydrosilylation of the resulting cycloalkynes catalyzed by [Cp*Ru(MeCN)(3)]PF6, and a protodesilylation of the ensuing vinylsilanes with AgF in aq. THF/MeOH. Moreover, the first examples of intramolecular enyne-yne metathesis reactions catalyzed by the Schrock alkylidyne complex (tBUO)(3)W drop CCMe3 are reported; the resulting cyclic enynes can be converted along similar lines into the corresponding (E,E)-configured 1,3-dienes in good overall yields. Cycloalkyne 4 and the (E)-configured cyclic olefins 6 and 21 were characterized by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.042