3,5-decadiyne-2-one | 74222-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-decadiyne-2-one
• 英文别名: deca-3,5-diyn-2-one；3,5-decadiyn-2-one
• CAS: 74222-58-5
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: PPKBSVWYQPIKLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-decadiyne-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94%的产率得到3,5-decadiyne-(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-bromohexyne 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 3,5-decadiyne-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

• Acylation reactions of silylated butadiynes: synthesis of some naturally occuring diacetylenic ketones
  作者：Graham E. Jones、Andrew B. Holmes

  DOI：10.1016/s0040-4039(00)88596-2

  日期：1982.1

  Acylation of 4-substituted 1-trimethylsilylbuta-1,3-diynes (2) with suitable acyl halides in the presence of titanium tetrachloride gave diacetylenic ketones (3) including the naturally occurring compounds (3c), (3e), and (3f).

  在四氯化钛存在下，将4-取代的1-trimethylsilylbuta-1,3-diynes（2）与合适的酰基卤酰化，得到二炔酮（3），包括天然存在的化合物（3c），（3e）和（3f） 。
• Synthesis of ?-acetylenic ketones by acylation of mercury acetylenides
  作者：B. P. Gusev、E. A. �l'perina、V. F. Kucherov

  DOI：10.1007/bf00949626

  日期：1980.3
• GUSEV B. P.; EHLPERINA E. A.; KUCHEROV V. F., IZV. AN CCCP CEP. XIM., 1980, HO 3, 600-603
  作者：GUSEV B. P.、 EHLPERINA E. A.、 KUCHEROV V. F.

  DOI：——

  日期：——
• 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.