(Z)-1-[(2S,5R)-2-Ethyl-5-(1-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-hex-4-en-1-one | 199927-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (Z)-1-[(2S,5R)-2-Ethyl-5-(1-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-hex-4-en-1-one
• 英文别名: (Z)-1-[(2S,5R)-2-ethyl-5-(2-hydroxypropan-2-yl)oxolan-2-yl]hex-4-en-1-one
• CAS: 199927-01-0
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: VODKDAXTJTZGBB-DOMBMUJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (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 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 32.3h， 生成 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：

  (Z,Z)-6-ethyl-2-methyl-6,10-dodecadien-2,3-diol 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以60%的产率得到(Z)-1-[(2S,5R)-2-Ethyl-5-(1-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-hex-4-en-1-one
  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

文献信息

• Sequential application of stereoselective syn-oxidation methodologies to natural product synthesis: A potentially biomimetic approach to the C12–C21 bistetrahydrofuran region of monensin
  作者：Frank E. McDonald、Colleen C. Schultz

  DOI：10.1016/s0040-4020(97)01026-0

  日期：1997.12

  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.