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

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-5α-allyl-2,3,5β-trichloro-1β-ethoxycarbonylmethyl-4,4-dimethoxy-2-cyclopenten-1α-ol
• 英文别名: ethyl 2-[(1R,5R)-2,3,5-trichloro-1-hydroxy-4,4-dimethoxy-5-prop-2-enylcyclopent-2-en-1-yl]acetate
• 化学式: C₁₄H₁₉Cl₃O₅
• 分子量: 373.661
• InChiKey: XRGNSLOJXGIWCA-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-5α-allyl-2,3,5β-trichloro-1β-ethoxycarbonylmethyl-4,4-dimethoxy-2-cyclopenten-1α-ol 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以90%的产率得到(+/-)-5α-allyl-1β-carboxymethyl-2,3,5β-trichloro-4,4-dimethoxy-2-cyclopenten-1α-ol
  参考文献：
  名称：

  摘要：

  The condensation of 5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with ethyl acetate lithium salt generated in situ in THF at -78degreesC gave adducts at the carbonyl group, the corresponding cis- and trans-chlorohydrins. The steric structure of the products was determined by involving them into reaction with iodine. From the trans-adduct the expected bicyclic compound was obtained, while the cis-chlorohydrin underwent anomalous deacetalization to iodomethoxycyclopentenone. Spectral parameters of the adducts were discussed. Unusual diastereotopicity was observed for the remote methylene groups in the ester moiety.

  DOI：

  10.1023/a:1019698603236
• 作为产物：
  描述：

  5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone 、 乙酸乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以64%的产率得到(+/-)-5α-allyl-2,3,5β-trichloro-1β-ethoxycarbonylmethyl-4,4-dimethoxy-2-cyclopenten-1α-ol
  参考文献：
  名称：

  摘要：

  The condensation of 5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with ethyl acetate lithium salt generated in situ in THF at -78degreesC gave adducts at the carbonyl group, the corresponding cis- and trans-chlorohydrins. The steric structure of the products was determined by involving them into reaction with iodine. From the trans-adduct the expected bicyclic compound was obtained, while the cis-chlorohydrin underwent anomalous deacetalization to iodomethoxycyclopentenone. Spectral parameters of the adducts were discussed. Unusual diastereotopicity was observed for the remote methylene groups in the ester moiety.

  DOI：

  10.1023/a:1019698603236

文献信息

• ——
  作者：N. S. Vostrikov、V. Z. Vasikov、L. V. Spirikhin、M. S. Miftakhov

  DOI：10.1023/a:1019698603236

  日期：——

  The condensation of 5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with ethyl acetate lithium salt generated in situ in THF at -78degreesC gave adducts at the carbonyl group, the corresponding cis- and trans-chlorohydrins. The steric structure of the products was determined by involving them into reaction with iodine. From the trans-adduct the expected bicyclic compound was obtained, while the cis-chlorohydrin underwent anomalous deacetalization to iodomethoxycyclopentenone. Spectral parameters of the adducts were discussed. Unusual diastereotopicity was observed for the remote methylene groups in the ester moiety.