3-ethynyl-3-(3-methoxyphenyl)pent-4-ynal | 1261299-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethynyl-3-(3-methoxyphenyl)pent-4-ynal
• CAS: 1261299-90-4
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: FACGHACSYAGKJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 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-ethynyl-3-(3-methoxyphenyl)pent-4-ynal 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以98%的产率得到3-ethynyl-3-(3-methoxyphenyl)pent-4-yn-1-ol
  参考文献：
  名称：

  Reversal of Selectivity in Gold-Catalyzed Cyclizations of 3,3-Disubstituted 1,4-Diynes

  摘要：

  A general synthetic access to 3,3-disubstituted 1,4-diynes bearing a quaternary carbon center from acetylacetone was developed. The compounds were cyclized to the corresponding enol ethers by cationic gold complexes. The reactions occur in complete exo-selectivity in contrast to compounds incorporating an alkoxy substituent in the 3-position. A mechanistic rationale for this reversal of selectivity is provided.

  DOI：

  10.1021/ol102628x
• 作为产物：
  描述：

  4-ethynyl-4-(3-methoxyphenyl)hex-5-yne-1,2-diol 在 silica gel-supported sodium periodate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到3-ethynyl-3-(3-methoxyphenyl)pent-4-ynal
  参考文献：
  名称：

  Reversal of Selectivity in Gold-Catalyzed Cyclizations of 3,3-Disubstituted 1,4-Diynes

  摘要：

  A general synthetic access to 3,3-disubstituted 1,4-diynes bearing a quaternary carbon center from acetylacetone was developed. The compounds were cyclized to the corresponding enol ethers by cationic gold complexes. The reactions occur in complete exo-selectivity in contrast to compounds incorporating an alkoxy substituent in the 3-position. A mechanistic rationale for this reversal of selectivity is provided.

  DOI：

  10.1021/ol102628x

文献信息

• Anion-Induced Enantioselective Cyclization of Diynamides to Pyrrolidines Catalyzed by Cationic Gold Complexes
  作者：Asmaa Kamal Mourad、Juliane Leutzow、Constantin Czekelius

  DOI：10.1002/anie.201205416

  日期：2012.10.29

  Only chiral anions do the job! Optically active gold complexes derived from substituted binol hydrogen phosphate catalyze the desymmetrizing cyclization of 1,4‐diynamides. This reaction provides access to synthetically useful, chiral methylene pyrrolidines with an all‐carbon‐substituted quaternary stereocenter.

  只有手性阴离子才能完成这项工作！衍生自取代的磷酸氢二酚的光学活性金络合物催化1,4-二乙酰胺的去对称化环化反应。该反应可提供具有全碳取代的季立体中心的合成有用的手性亚甲基吡咯烷。