6-(1-(benzyloxy)cyclohexyl)-3,5-hexadiyn-2-one | 1527466-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(1-(benzyloxy)cyclohexyl)-3,5-hexadiyn-2-one
• 英文别名: 6-(1-Phenylmethoxycyclohexyl)hexa-3,5-diyn-2-one；6-(1-phenylmethoxycyclohexyl)hexa-3,5-diyn-2-one
• CAS: 1527466-60-9
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: IPTVRQFIJQAFLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(1-(benzyloxy)cyclohexyl)-3,5-hexadiyn-2-one 在 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 甲酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到6-(1-(benzyloxy)cyclohexyl)-3,5-hexadiyn-(2S)-ol
  参考文献：
  名称：

  Asymmetric Reduction of Diynones and the Total Synthesis of (S)-Panaxjapyne A

  摘要：

  The asymmetric transfer hydrogenation of a series of diynones has been achieved in high conversion and enantiomeric induction. When R-1 is a phenyl group, a competing alkyne reduction takes place; however, when R-1 is an alkyl group, this side-reaction is not observed. The application of the reduction to the total synthesis of the natural product (S)-panaxjapyne A in high enantiomeric excess is described.

  DOI：

  10.1021/ol4032123
• 作为产物：
  描述：

  (((1-ethynylcyclohexyl)oxy)methyl)benzene 在 manganese(IV) oxide 、 盐酸羟胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 氘代氯仿 、 水 、 正丁醇 为溶剂， 反应 0.08h， 生成 6-(1-(benzyloxy)cyclohexyl)-3,5-hexadiyn-2-one
  参考文献：
  名称：

  Asymmetric Reduction of Diynones and the Total Synthesis of (S)-Panaxjapyne A

  摘要：

  The asymmetric transfer hydrogenation of a series of diynones has been achieved in high conversion and enantiomeric induction. When R-1 is a phenyl group, a competing alkyne reduction takes place; however, when R-1 is an alkyl group, this side-reaction is not observed. The application of the reduction to the total synthesis of the natural product (S)-panaxjapyne A in high enantiomeric excess is described.

  DOI：

  10.1021/ol4032123

文献信息

• Asymmetric Reduction of Diynones and the Total Synthesis of (<i>S</i>)-Panaxjapyne A
  作者：Zhijia Fang、Martin Wills

  DOI：10.1021/ol4032123

  日期：2014.1.17

  The asymmetric transfer hydrogenation of a series of diynones has been achieved in high conversion and enantiomeric induction. When R-1 is a phenyl group, a competing alkyne reduction takes place; however, when R-1 is an alkyl group, this side-reaction is not observed. The application of the reduction to the total synthesis of the natural product (S)-panaxjapyne A in high enantiomeric excess is described.