(+/-)-2,3,5β-trichloro-5α-formylmethyl-4,4-dimethoxy-1α-phenylethynyl-2-cyclopenten-1β-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-2,3,5β-trichloro-5α-formylmethyl-4,4-dimethoxy-1α-phenylethynyl-2-cyclopenten-1β-ol
• 英文别名: 2-[(1R,2S)-1,3,4-trichloro-2-hydroxy-5,5-dimethoxy-2-(2-phenylethynyl)cyclopent-3-en-1-yl]acetaldehyde
• 化学式: C₁₇H₁₅Cl₃O₄
• 分子量: 389.663
• InChiKey: DHXPTKKKAMCQGL-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone 在 氧气 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (+/-)-2,3,5β-trichloro-5α-formylmethyl-4,4-dimethoxy-1α-phenylethynyl-2-cyclopenten-1β-ol
  参考文献：
  名称：

  摘要：

  Condensation of (+/-)-5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with phenylethynyl-magnesium bromide in THF gave (+/-)-5 alpha -allyl-2,3,5 beta -trichloro-4,4-dimethoxy-1 alpha -phenylethynyl-2-cyclopenten-1 beta -ol which chemoselectively reacted with ozone at the terminal double bond, affording (+/-)-2,3,5 beta -trichloro-5 alpha -formylmethyl-4,4-dimethoxy-1 alpha -phenylethynyl-2-cyclopenten-1 beta -ol. Oxidation of the latter with H2CrO4 yielded a mixture of the expected product, (+/-)-5 alpha -carboxymethyl-2,3,5 beta -trichloro-4,4-dimethoxy-1 alpha -phenylethynyl-2-cyclopenten-1 beta -ol, and anomalous profound oxidation product, (+/-)-2,3,5 beta -trichloro-5 alpha -carboxymethyl-4,4-dimethoxy-1 alpha-(2-oxo-2-phenylacetyl)-2-cyclopenten-1 beta -ol. Attempts to remove protective methoxy groups in these compounds under standard conditions were unsuccessful.

  DOI：

  10.1023/a:1012324306438

文献信息

• ——
  作者：F. A. Akbutina、S. A. Torosyan、M. S. Miftakhov

  DOI：10.1023/a:1012324306438

  日期：——

  Condensation of (+/-)-5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with phenylethynyl-magnesium bromide in THF gave (+/-)-5 alpha -allyl-2,3,5 beta -trichloro-4,4-dimethoxy-1 alpha -phenylethynyl-2-cyclopenten-1 beta -ol which chemoselectively reacted with ozone at the terminal double bond, affording (+/-)-2,3,5 beta -trichloro-5 alpha -formylmethyl-4,4-dimethoxy-1 alpha -phenylethynyl-2-cyclopenten-1 beta -ol. Oxidation of the latter with H2CrO4 yielded a mixture of the expected product, (+/-)-5 alpha -carboxymethyl-2,3,5 beta -trichloro-4,4-dimethoxy-1 alpha -phenylethynyl-2-cyclopenten-1 beta -ol, and anomalous profound oxidation product, (+/-)-2,3,5 beta -trichloro-5 alpha -carboxymethyl-4,4-dimethoxy-1 alpha-(2-oxo-2-phenylacetyl)-2-cyclopenten-1 beta -ol. Attempts to remove protective methoxy groups in these compounds under standard conditions were unsuccessful.