(Z,Z)-6-ethyl-2-methyl-6,10-dodecadien-2,3-diol | 199926-95-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z,Z)-6-ethyl-2-methyl-6,10-dodecadien-2,3-diol
• 英文别名: (3R,6Z,10Z)-6-ethyl-2-methyldodeca-6,10-diene-2,3-diol
• CAS: 199926-95-9
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: SUZNAKDYQNCTGG-JKXAKYBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z,Z)-6-ethyl-2-methyl-6,10-dodecadien-2,3-diol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以24%的产率得到(Z)-(R)-1-[(2S,5R)-2-Ethyl-5-(1-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-hex-4-en-1-ol
  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)-4-ethyl-1,4,8-decatriene 在 9-borabicyclo[3.3.1]nonane dimer 、 甲基磺酰胺 、 Celite 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 、 正戊烷 为溶剂， 反应 14.5h， 生成 (Z,Z)-6-ethyl-2-methyl-6,10-dodecadien-2,3-diol
  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.