triptoquinone C | 142937-49-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: triptoquinone C
• 英文别名: (4bS,7S,8S,8aR)-7-hydroxy-8-(hydroxymethyl)-4b,8-dimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-1,4-dione
• CAS: 142937-49-3
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: ACIVVOUFLGSCLJ-GIYDNNGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  triptoquinone C 在 sodium hypochlorite 作用下， 以 溶剂黄146 为溶剂， 以89%的产率得到雷藤二萜醌 B
  参考文献：
  名称：

  Enantiocontrolled total synthesis of the diterpenoids, triptoquinone B, C and triptocallol

  摘要：

  An efficient and enantiocontrolled synthesis of triptoquinone B and C, which possess interleukin-1 inhibitory activity, has been accomplished employing the lipase-catalyzed kinetic resolution and a highly diastereoselective radical cyclization as key synthetic steps. In addition, the first total synthesis of triptocallol has been achieved utilizing the same strategy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00841-1
• 作为产物：
  描述：

  (1S,4aS,10aR)-5,8-Dihydroxy-1-hydroxymethyl-7-isopropyl-1,4a-dimethyl-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one 在 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 、 乙腈 为溶剂， 反应 4.33h， 生成 triptoquinone C
  参考文献：
  名称：

  Synthetic studies on diterpenoid quinones with interleukin-1 inhibitory activity. Total synthesis of (.+-.)- and (+)-triptoquinone A

  摘要：

  An efficient first total synthesis of (+/-)- and (+)-triptoquinone A (1), a novel diterpenoid quinone with significant inhibitory activity against interleukin-1 releases, has been completed. Birch reduction of tricyclic enone (+/-)-7, prepared from known 6-methoxy-2-isopropyl-1-naphthol (22), which is readily available in large quantities, was followed by immediate enolate trapping to provide silyl enol ether (+/-)-30. Compound 30 was converted into carboxylic acid (+/-)-4 via the corresponding enol triflate (+/-)-31 either by sequential palladium-catalyzed carbonylation and oxidation or by direct carboxylation. The total synthesis of (+/-)-1 was completed by oxidation of (+/-)-4 with CAN in 12 steps from 22 in 19% overall yield at best. A second, enantioselective total synthesis of (+)-1 was accomplished via (+/-)-7, which was prepared by (-)-N- [4-(trifluoromethyl)benzyl]cinchonidinium bromide (33) catalyzed asymmetric Michael reaction of 6 with ethyl vinyl ketone and a subsequent aldol condensation. The absolute structures of triptoquinone B (2) and C (3), which were isolated concomitantly with triptoquinone A from the same plant sources, were established by a series of chemical reactions based on (+)-7.

  DOI：

  10.1021/jo00081a021

文献信息

• Modular Terpenoid Construction via Catalytic Enantioselective Formation of All-Carbon Quaternary Centers: Total Synthesis of Oridamycin A, Triptoquinones B and C, and Isoiresin
  作者：Jiajie Feng、Florian Noack、Michael J. Krische

  DOI：10.1021/jacs.6b08902

  日期：2016.9.28

  Total syntheses of oridamycin A, triptoquinones B and C, and isoiresin are accomplished from a common intermediate prepared via iridium-catalyzed alcohol C-H tert-(hydroxy)prenylation - a byproduct-free process that forms an all-carbon quaternary stereocenter with excellent control of diastereo- and enantioselectivity.

  Oridamycin A、triptoquinones B 和 C 以及异香豆素的全合成是从通过铱催化的醇 CH 叔-（羟基）异戊二烯化制备的普通中间体完成的 - 一种无副产物的过程，形成一个全碳四元立体中心，具有极好的控制非对映选择性和对映选择性。
• Synthetic studies on diterpenoid quinones with interleukin-1 inhibitory activity. Total synthesis of (.+-.)- and (+)-triptoquinone A
  作者：Kozo Shishido、Kiyoto Goto、Shizuka Miyoshi、Yoshihisa Takaishi、Masayuki Shibuya

  DOI：10.1021/jo00081a021

  日期：1994.1

  An efficient first total synthesis of (+/-)- and (+)-triptoquinone A (1), a novel diterpenoid quinone with significant inhibitory activity against interleukin-1 releases, has been completed. Birch reduction of tricyclic enone (+/-)-7, prepared from known 6-methoxy-2-isopropyl-1-naphthol (22), which is readily available in large quantities, was followed by immediate enolate trapping to provide silyl enol ether (+/-)-30. Compound 30 was converted into carboxylic acid (+/-)-4 via the corresponding enol triflate (+/-)-31 either by sequential palladium-catalyzed carbonylation and oxidation or by direct carboxylation. The total synthesis of (+/-)-1 was completed by oxidation of (+/-)-4 with CAN in 12 steps from 22 in 19% overall yield at best. A second, enantioselective total synthesis of (+)-1 was accomplished via (+/-)-7, which was prepared by (-)-N- [4-(trifluoromethyl)benzyl]cinchonidinium bromide (33) catalyzed asymmetric Michael reaction of 6 with ethyl vinyl ketone and a subsequent aldol condensation. The absolute structures of triptoquinone B (2) and C (3), which were isolated concomitantly with triptoquinone A from the same plant sources, were established by a series of chemical reactions based on (+)-7.
• Enantiocontrolled total synthesis of the diterpenoids, triptoquinone B, C and triptocallol
  作者：Itsuki Yamamura、Yoko Fujiwara、Toshihiro Yamato、Osamu Irie、Kozo Shishido

  DOI：10.1016/s0040-4039(97)00841-1

  日期：1997.6

  An efficient and enantiocontrolled synthesis of triptoquinone B and C, which possess interleukin-1 inhibitory activity, has been accomplished employing the lipase-catalyzed kinetic resolution and a highly diastereoselective radical cyclization as key synthetic steps. In addition, the first total synthesis of triptocallol has been achieved utilizing the same strategy. (C) 1997 Elsevier Science Ltd.