(3S)-hept-1-ene-4,6-diyn-3-ol | 405144-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-hept-1-ene-4,6-diyn-3-ol
• 英文别名: (S)-hept-1-ene-4,6-diyn-3-ol；(3S)-hept-1-en-4,6-diyn-3-ol
• CAS: 405144-93-6
• 化学式: C₇H₆O
• 分子量: 106.124
• InChiKey: QDWDAWJYZMHUPK-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S)-hept-1-ene-4,6-diyn-3-ol 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.75h， 生成 (3S,9R,10R)-heptadec-1-ene-4,6-diyne-3,9,10-triol
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

  摘要：

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

  DOI：

  10.1021/jo020073w
• 作为产物：
  描述：

  rac-hept-1-ene-4,6-diyn-3-ol 在 4-二甲氨基吡啶 、 Candida antarctica B lipase 、 Na₂HPO₄ buffer 、 三乙胺 作用下， 反应 7.5h， 生成 (3S)-hept-1-ene-4,6-diyn-3-ol
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

  摘要：

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

  DOI：

  10.1021/jo020073w

文献信息

• Absolute Structure of Panaxytriol.
  作者：Mitsuru Satoh、Masayoshi Ishii、Mitsuo Watanabe、Kimiaki Isobe、Taketo Uchiyama、Yasuo Fujimoto

  DOI：10.1248/cpb.50.126

  日期：——

  Diastereomeric mixture at C-3 of (9R, 10R)-panaxytriol acetonide (3) and (9S, 10S)-panaxytriol acetonide (4) were enantioselectively acetylated to give (3R)-acetates (3a-Ac, 4a-Ac) and (3S)-alcohols (3b, 4b) by enzyme mediated-acetylation using CHIRAZYME and vinyl acetate, respectively. Hydrolysis of (3R)-acetate (3a-Ac, 4a-Ac) with CHIRAZYME and phosphate buffer afforded (3R)-alcohols (3a, 4a), respectively. Deprotection of panaxytriol acetonides (3a, 3b, 4a, 4b) gave panaxatriol and its isomers, respectively. Comparison of optical rotation values of the synthetic panaxatriols with that of the natural one confirmed that the absolute configuration of panaxytriol sould be 3R, 9R, 10R.

  通过使用 CHIRAZYME 和乙酸乙烯酯进行酶介导乙酰化，(9R, 10R)-panaxytriol acetonide (3) 和 (9S, 10S)-panaxytriol acetonide (4) C-3 处的非对映混合物被对映选择性乙酰化，分别得到 (3R)-acetates (3a-Ac, 4a-Ac) 和 (3S)-alcohols (3b, 4b)。用 CHIRAZYME 和磷酸盐缓冲液水解 (3R)-acetate (3a-Ac, 4a-Ac)，分别得到 (3R)-alcohols (3a, 4a)。对三羟甲基丙酮（3a、3b、4a、4b）进行脱保护处理后，分别得到三羟甲基丙酮及其异构体。通过比较合成的三七酚与天然三七酚的旋光度值，证实三七酚的绝对构型应为 3R、9R、10R。