[9-3H]coniferyl alcohol | 140215-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [9-3H]coniferyl alcohol
• CAS: 140215-89-0
• 化学式: C₁₀H₁₂O₃
• 分子量: 182.196
• InChiKey: JMFRWRFFLBVWSI-NGIXYFTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [9-3H]coniferyl alcohol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以28.6%的产率得到[9-3H]coniferyl alcohol dimesylate
  参考文献：
  名称：

  Biosynthesis of antimalarial lignans from Holostylis reniformis

  摘要：

  Holostylis reniformis biosynthesizes 8-8' linked lignans without 9,9'-oxygenation. To elucidate the biosynthetic pathways to these lignans, the reputed precursors [U-C-14]phenylalanine, [9-H-3(1)]coniferyl alcohol, and [9-H-3(1)]isoeugenol were administered to roots of the plant, which led to the incorporation of H-3 and C-14 into ten 2,7' linked-lignans (aryltetralone lignans) and two 7,7'-epoxylignans (furan lignans). These administration experiments demonstrated that the lignans were propenylphenol-derived and that H. reniformis can exhibit regioselective control over radical-radical coupling (via isoeugenol radicals). Regiospecific control over propenylphenol-derived lignan biosynthesis was observed, together with diastereoselective control of C2-C7' bond formation for the aryltetralone lignans (7'R). These experiments provide evidence that isoeugenol is a biosynthetic intermediate to the aryltetralone and furan lignans. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.02.008
• 作为产物：
  描述：

  4-羟基-3-甲氧基肉桂醛 在 sodium borotritide 、 水 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到[9-3H]coniferyl alcohol
  参考文献：
  名称：

  Biosynthesis of antimalarial lignans from Holostylis reniformis

  摘要：

  Holostylis reniformis biosynthesizes 8-8' linked lignans without 9,9'-oxygenation. To elucidate the biosynthetic pathways to these lignans, the reputed precursors [U-C-14]phenylalanine, [9-H-3(1)]coniferyl alcohol, and [9-H-3(1)]isoeugenol were administered to roots of the plant, which led to the incorporation of H-3 and C-14 into ten 2,7' linked-lignans (aryltetralone lignans) and two 7,7'-epoxylignans (furan lignans). These administration experiments demonstrated that the lignans were propenylphenol-derived and that H. reniformis can exhibit regioselective control over radical-radical coupling (via isoeugenol radicals). Regiospecific control over propenylphenol-derived lignan biosynthesis was observed, together with diastereoselective control of C2-C7' bond formation for the aryltetralone lignans (7'R). These experiments provide evidence that isoeugenol is a biosynthetic intermediate to the aryltetralone and furan lignans. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.02.008