Acetic acid 1-[(2R,5S)-5-ethyl-5-((Z)-hex-4-enoyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester | 199926-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid 1-[(2R,5S)-5-ethyl-5-((Z)-hex-4-enoyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester
• CAS: 199926-81-3
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: BIDHSAGGAWTLPU-AKTONZINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid 1-[(2R,5S)-5-ethyl-5-((Z)-hex-4-enoyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 2.3h， 以94%的产率得到Acetic acid 1-[(2R,5S)-5-ethyl-5-((Z)-(R)-1-hydroxy-hex-4-enyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester
  参考文献：
  名称：

  Sequential application of stereoselective syn-oxidation methodologies to natural product synthesis: A potentially biomimetic approach to the C12–C21 bistetrahydrofuran region of monensin

  摘要：

  The preparation of an all-Z-triene corresponding to an acyclic premonensin triene is described. In analogy to the Townsend syn-oxidative cyclization hypothesis for natural product biosynthesis, a sequence of regioselective and enantioselective syn-dihydroxylation of the triene, cis-selective syn-oxidative cyclization of the diol-diene, and trans-selective syn-oxidative cyclization of the remaining hydroxyalkene gives the correct stereochemical pattern corresponding to the C and D ring tetrahydrofurans of monensin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01026-0
• 作为产物：
  描述：

  乙酸酐 、 (Z)-1-[(2S,5R)-2-Ethyl-5-(1-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-hex-4-en-1-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 30.0h， 以97%的产率得到Acetic acid 1-[(2R,5S)-5-ethyl-5-((Z)-hex-4-enoyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester
  参考文献：
  名称：

  Sequential application of stereoselective syn-oxidation methodologies to natural product synthesis: A potentially biomimetic approach to the C12–C21 bistetrahydrofuran region of monensin

  摘要：

  The preparation of an all-Z-triene corresponding to an acyclic premonensin triene is described. In analogy to the Townsend syn-oxidative cyclization hypothesis for natural product biosynthesis, a sequence of regioselective and enantioselective syn-dihydroxylation of the triene, cis-selective syn-oxidative cyclization of the diol-diene, and trans-selective syn-oxidative cyclization of the remaining hydroxyalkene gives the correct stereochemical pattern corresponding to the C and D ring tetrahydrofurans of monensin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01026-0