(1S,2R,4S,5Z)-5-[(acetyloxy)methylene]-2-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohexane-1,4-diol 4-acetate | 276253-30-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,4S,5Z)-5-[(acetyloxy)methylene]-2-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohexane-1,4-diol 4-acetate
• 英文别名: [(Z)-[(2S,4R,5S)-2-acetyloxy-5-hydroxy-4-(6-methylhepta-1,5-dien-3-yn-2-yl)cyclohexylidene]methyl] acetate
• CAS: 276253-30-6
• 化学式: C₁₉H₂₄O₅
• 分子量: 332.397
• InChiKey: LDWFYDXUXAFPBW-QESSFWTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,4S,5Z)-5-[(acetyloxy)methylene]-2-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohexane-1,4-diol 4-acetate 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 acetyl volvatellin
  参考文献：
  名称：

  (+)-(1S,6R)-Volvatellin (=(+)-(4R,5S)-5-Hydroxy-4-(5-methyl-1-methylenehex-4-en-2) 的高度非对映选择性生物遗传模式合成-ynyl)cyclohex-1-ene-1-carbaldehyde)

  摘要：

  The synthesis of volvatellin (4a), previously isolated from a herbivorous marine mollusk, was achieved with high diastereoselectivity from putative dietary oxytoxin-1 (2). A biogenetically patterned carbonyl-ene route was chosen. proceeding from 2 predominantly via the trans cyclization product 3 without the use of enzymes. This challenges the involvement of enzymes in the formation of 4a in nature. The optical purity and absolute configuration (1S,4S,6R). assigned to 3 from high-field H-1-NMR examination of its Mosher (MTPA) esters 6. was retained on its chemical conversion to (+)-(1S,6R)-configured 4a and is consistent with the (4S) configuration previously, established for caulerpenyne (1).

  DOI：

  10.1002/(sici)1522-2675(20000412)83:4<694::aid-hlca694>3.0.co;2-3
• 作为产物：
  描述：

  oxytoxin-1 在 二氯乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到(1S,2R,4S,5Z)-5-[(acetyloxy)methylene]-2-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohexane-1,4-diol 4-acetate
  参考文献：
  名称：

  (+)-(1S,6R)-Volvatellin (=(+)-(4R,5S)-5-Hydroxy-4-(5-methyl-1-methylenehex-4-en-2) 的高度非对映选择性生物遗传模式合成-ynyl)cyclohex-1-ene-1-carbaldehyde)

  摘要：

  The synthesis of volvatellin (4a), previously isolated from a herbivorous marine mollusk, was achieved with high diastereoselectivity from putative dietary oxytoxin-1 (2). A biogenetically patterned carbonyl-ene route was chosen. proceeding from 2 predominantly via the trans cyclization product 3 without the use of enzymes. This challenges the involvement of enzymes in the formation of 4a in nature. The optical purity and absolute configuration (1S,4S,6R). assigned to 3 from high-field H-1-NMR examination of its Mosher (MTPA) esters 6. was retained on its chemical conversion to (+)-(1S,6R)-configured 4a and is consistent with the (4S) configuration previously, established for caulerpenyne (1).

  DOI：

  10.1002/(sici)1522-2675(20000412)83:4<694::aid-hlca694>3.0.co;2-3

文献信息

• Highly Diastereoselective, Biogenetically Patterned Synthesis of (+)-(1S,6R)-Volvatellin (=(+)-(4R,5S)-5-Hydroxy-4-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohex-1-ene-1-carbaldehyde)
  作者：Ines Mancini、Graziano Guella、Francesco Pietra

  DOI：10.1002/(sici)1522-2675(20000412)83:4<694::aid-hlca694>3.0.co;2-3

  日期：2000.4.12

  The synthesis of volvatellin (4a), previously isolated from a herbivorous marine mollusk, was achieved with high diastereoselectivity from putative dietary oxytoxin-1 (2). A biogenetically patterned carbonyl-ene route was chosen. proceeding from 2 predominantly via the trans cyclization product 3 without the use of enzymes. This challenges the involvement of enzymes in the formation of 4a in nature. The optical purity and absolute configuration (1S,4S,6R). assigned to 3 from high-field H-1-NMR examination of its Mosher (MTPA) esters 6. was retained on its chemical conversion to (+)-(1S,6R)-configured 4a and is consistent with the (4S) configuration previously, established for caulerpenyne (1).