deoxytrisporone | 29538-78-1

• 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: deoxytrisporone
• 英文别名: (2E,4E)-3-methyl-5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienol；Deoxytrisporon；3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-one；3-[5-hydroxy-3-methyl-1E,3E-pentadienyl]-2,4,4-trimethyl-2-cyclohexen-1-one；3-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dienyl]-2,4,4-trimethylcyclohex-2-en-1-one
• CAS: 29538-78-1
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: BVUBYYWRFBEIET-BXROQLSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  deoxytrisporone 在 lithium diisopropyl amide 、 (+)-8,8-二氯樟脑磺哑嗪 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 以69%的产率得到(E)-6-Hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-on
  参考文献：
  名称：

  Synthesis and Characterization ofall-E-(4,4′-13C2)-Astaxanthin Strategies for Labelling the C15-End Groups of Carotenoids

  摘要：

  The all-E isomer of (4,4'-C-13(2))astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% C-13 enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C-15 + C-10 + C-15 strategy was used. The central C-10-synthon, 2,7-dimethylocta-2,4,6-triene-1,8-dial (3), was coupled with C-13-enriched C-15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C-15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C-15-phosphonium salt.

  DOI：

  10.1002/(sici)1099-0690(200003)2000:5<829::aid-ejoc829>3.0.co;2-z
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 在 盐酸 、 正丁基锂 、 硫酸 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 lithium diisopropyl amide 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 Petroleum ether 为溶剂， 反应 4.5h， 生成 deoxytrisporone
  参考文献：
  名称：

  Synthesis and Characterization ofall-E-(4,4′-13C2)-Astaxanthin Strategies for Labelling the C15-End Groups of Carotenoids

  摘要：

  The all-E isomer of (4,4'-C-13(2))astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% C-13 enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C-15 + C-10 + C-15 strategy was used. The central C-10-synthon, 2,7-dimethylocta-2,4,6-triene-1,8-dial (3), was coupled with C-13-enriched C-15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C-15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C-15-phosphonium salt.

  DOI：

  10.1002/(sici)1099-0690(200003)2000:5<829::aid-ejoc829>3.0.co;2-z

文献信息

• All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use
  申请人：Moise Alexander R.

  公开号：US20080249042A1

  公开（公告）日：2008-10-09

  Compositions of all-trans-retinol: all-trans-13,14-dihydroretinal saturase and methods of use thereof are provided.

  提供了全反式视黄醇的组合物：全反式-13,14-二氢视黄醛饱和酶及其使用方法。
• Process for carotenoid intermediates
  申请人：Hoffmann-La Roche Inc.

  公开号：US04701540A1

  公开（公告）日：1987-10-20

  A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.

  通过这种方法可以生产5或6碳链长度的环酮，这些酮是生产类胡萝卜素的已知中间体。
• Synthetic Photochemistry. XXVII. An Efficient Synthesis of Deoxytrisporone by Photocycloaddition
  作者：Hitoshi Takeshita、Seiji Hatta、Toshihide Hatsui

  DOI：10.1246/bcsj.57.619

  日期：1984.2

  Deoxytrisporone was synthesized from isobutene and methyl 2,4-dioxohexanoate to show the utility of the regioselective photocycloaddition of β-diketone for construction of polysubstituted cyclohexenones.

  Deoxytrisporone 由异丁烯和 2,4-二氧己酸甲酯合成，以显示 β-二酮的区域选择性光环加成在构建多取代环己烯酮中的效用。
• Verfahren zur Herstellung von Cyclohexenderivaten
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0031875B1

  公开（公告）日：1983-05-18
• Verfahren zur Herstellung von Pentadienol-Derivaten
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0120341B1

  公开（公告）日：1989-01-25