(4R,5S,7S,8R,11R)-2,12,12,12-tetradeuterio-7,8-dihydroxy-1-oxoquiroga-2,9-diene | 372112-26-0

• 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: (4R,5S,7S,8R,11R)-2,12,12,12-tetradeuterio-7,8-dihydroxy-1-oxoquiroga-2,9-diene
• CAS: 372112-26-0
• 化学式: C₁₅H₂₀O₃
• 分子量: 252.29
• InChiKey: ZTYOXJAAZQVRBX-DLXOMQMBSA-N

反应信息

• 作为反应物：
  描述：

  (4R,5S,7S,8R,11R)-2,12,12,12-tetradeuterio-7,8-dihydroxy-1-oxoquiroga-2,9-diene 在 过碘酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以74%的产率得到
  参考文献：
  名称：

  Generation of the new quirogane skeleton by a vinylogous retro-Michael type rearrangement of longipinene derivatives

  摘要：

  A new tricyclic hydrocarbon skeleton, named quirogane, was prepared by a vinylogous retro-Michael type molecular rearrangement of (4R,5S,7R,8R,9S,10R,11R)-7,8-diacetyloxy-9-mesyloxy-1-oxolongipin-2-ene (5). A remarkable difference in chemical behavior as compared to the corresponding 2,3-dihydroderivative of 5 is explained in terms of the stability of anionic intermediates, which were evaluated by AMI calculations. The structure of the quirogane skeleton was confirmed by single crystal X-ray diffraction analysis of quirogadiene 6. A [2+2] photochemical cyclization of 6 afforded the highly strained pentacyclic sesquiterpenoid (10). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00718-9
• 作为产物：
  描述：

  Acetic acid (1R,4aR,5R,6S,7S,8S,9aS)-8-acetoxy-6-hydroxy-4,5,9,9-tetramethyl-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-1,5-cyclo-benzocyclohepten-7-yl ester 在 吡啶 、 氢氧化钾 、 氘代甲醇-d 、 水 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 34.0h， 生成 (4R,5S,7S,8R,11R)-2,12,12,12-tetradeuterio-7,8-dihydroxy-1-oxoquiroga-2,9-diene
  参考文献：
  名称：

  Generation of the new quirogane skeleton by a vinylogous retro-Michael type rearrangement of longipinene derivatives

  摘要：

  A new tricyclic hydrocarbon skeleton, named quirogane, was prepared by a vinylogous retro-Michael type molecular rearrangement of (4R,5S,7R,8R,9S,10R,11R)-7,8-diacetyloxy-9-mesyloxy-1-oxolongipin-2-ene (5). A remarkable difference in chemical behavior as compared to the corresponding 2,3-dihydroderivative of 5 is explained in terms of the stability of anionic intermediates, which were evaluated by AMI calculations. The structure of the quirogane skeleton was confirmed by single crystal X-ray diffraction analysis of quirogadiene 6. A [2+2] photochemical cyclization of 6 afforded the highly strained pentacyclic sesquiterpenoid (10). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00718-9