1,2-epoxy-3-([2H3]methyl)-7-methyl[4-2H2]octa-6-en-3-ol | 1306663-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-epoxy-3-([2H3]methyl)-7-methyl[4-2H2]octa-6-en-3-ol
• 英文别名: d5-rac-1,2-epoxylinalool
• CAS: 1306663-91-1
• 化学式: C₁₀H₁₈O₂
• 分子量: 175.212
• InChiKey: BXOURKNXQXLKRK-SBRIIUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,2-epoxy-3-([2H3]methyl)-7-methyl[4-2H2]octa-6-en-3-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到[4', 4', 8', 8', 8'-2H5]-2-(5-methyl-5-(oxiran-2-yl)-tetrahydrofuran-2-yl)propanal
  参考文献：
  名称：

  Biosynthesis and enantioselectivity in the production of the lilac compounds in Actinidia arguta flowers

  摘要：

  Biosynthesis of the lilac alcohols and alcohol epoxides from linalool in 'Hortgem Tahi' kiwifruit (Actinidiaarguta) flowers was investigated by incubating flowers with rac-linalool, rac-[4,4,10,10,10-H-2(5)]linalool, (R)-8-hydroxylinalool and (R)-8-oxolinalool. All substrates were incorporated into the lilac alcohols although the (R)-configured compounds are not normally present in flowers. Biosynthesis of the lilac alcohol epoxides from rac-1,2-epoxy[4,4,10,10,10-H-2(5)]linalool and rac-[4',4', 8', 8',8'-H-2(5)]lilac aldehyde epoxide, rather than the lilac alcohols, was examined. Both substrates were non-enantioselectively converted to the lilac alcohol epoxides, suggesting two biosynthetic pathways for these compounds, contrary to previous reports. Their ability to process unnatural substrates indicates that A.arguta flowers have a greater biosynthetic capability than is suggested by their phytochemical composition. Linalool, the lilac compounds, and their biosynthetic intermediates were measured in the pistils, stamen, petals and sepals to determine if localisation in different organs contributed to only (S)-linalool being processed to the lilac compounds. Both linalool enantiomers were present in all organs, while most (97%) of the lilac compounds, and their precursors, were found in the petals. (S)-Linalool was not depleted from the flower petals, with respect to (R)-linalool, during the time of maximum production of the metabolites of (S)-linalool. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.01.035
• 作为产物：
  描述：

  linalool-d5 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 生成 1,2-epoxy-3-([2H3]methyl)-7-methyl[4-2H2]octa-6-en-3-ol
  参考文献：
  名称：

  Biosynthesis and enantioselectivity in the production of the lilac compounds in Actinidia arguta flowers

  摘要：

  Biosynthesis of the lilac alcohols and alcohol epoxides from linalool in 'Hortgem Tahi' kiwifruit (Actinidiaarguta) flowers was investigated by incubating flowers with rac-linalool, rac-[4,4,10,10,10-H-2(5)]linalool, (R)-8-hydroxylinalool and (R)-8-oxolinalool. All substrates were incorporated into the lilac alcohols although the (R)-configured compounds are not normally present in flowers. Biosynthesis of the lilac alcohol epoxides from rac-1,2-epoxy[4,4,10,10,10-H-2(5)]linalool and rac-[4',4', 8', 8',8'-H-2(5)]lilac aldehyde epoxide, rather than the lilac alcohols, was examined. Both substrates were non-enantioselectively converted to the lilac alcohol epoxides, suggesting two biosynthetic pathways for these compounds, contrary to previous reports. Their ability to process unnatural substrates indicates that A.arguta flowers have a greater biosynthetic capability than is suggested by their phytochemical composition. Linalool, the lilac compounds, and their biosynthetic intermediates were measured in the pistils, stamen, petals and sepals to determine if localisation in different organs contributed to only (S)-linalool being processed to the lilac compounds. Both linalool enantiomers were present in all organs, while most (97%) of the lilac compounds, and their precursors, were found in the petals. (S)-Linalool was not depleted from the flower petals, with respect to (R)-linalool, during the time of maximum production of the metabolites of (S)-linalool. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.01.035