5,8-Dimethoxy-6-isopropyl-1-methyl-2-tetralone | 146356-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,8-Dimethoxy-6-isopropyl-1-methyl-2-tetralone
• 英文别名: 5,8-dimethoxy-6-isopropyl-1-methyl-3,4-dihydro-2(1H)-naphthalenone；5,8-dimethoxy-1-methyl-6-propan-2-yl-3,4-dihydro-1H-naphthalen-2-one
• CAS: 146356-64-1
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: KAVFEVNSNIEFOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,8-Dimethoxy-6-isopropyl-1-methyl-2-tetralone 在 氢氧化钾 、 氨 、 甲基锂 、 lithium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 生成 (4aS*,10aR*)-5,8-Dimethoxy-1,4a-dimethyl-7-isopropyl-2-(trifluoromethanesulfonyloxy)-3,4,4a,9,10,10a-hexahydrophenanthrene
  参考文献：
  名称：

  Total synthesis of (±)-triptoquinone A

  摘要：

  A concise and practical total synthesis of (+/-)-triptoquinone A (1), a novel interleukin-1 inhibitor isolated from Tripterygium wilfordii var. regelii, has been achieved in 11 steps from the known naphthol 2.

  DOI：

  10.1016/s0040-4039(00)60582-8
• 作为产物：
  描述：

  4-溴-2-异丙基苯酚 在 sodium hydroxide 、 sodium chlorite 、 copper(l) iodide 、 草酰氯 、 dimethyl sulfide borane 、 氨基磺酸 、 双氧水 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 29.63h， 生成 5,8-Dimethoxy-6-isopropyl-1-methyl-2-tetralone
  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

• NITROGEN MONOXIDE SYNTHESIS INHIBITOR
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0676196A1

  公开（公告）日：1995-10-11

  A nitrogen monoxide synthesis inhibitor containing as the active ingredient at least one member selected from phenanthrene derivatives represented by the compounds of general formula (1) and salts thereof; it is useful for preventing and treating various diseases caused by nitrogen monoxide, such as endotoxin shock.

  一种一氧化氮合成抑制剂，含有至少一种选自通式（1）化合物所代表的菲衍生物及其盐类的活性成分；可用于预防和治疗一氧化氮引起的各种疾病，如内毒素休克。
• Total synthesis of (±)-triptoquinone A
  作者：Kozo Shishido、Kiyoto Goto、Shizuka Miyoshi、Yoshihisa Takaishi、Masayuki Shibuya

  DOI：10.1016/s0040-4039(00)60582-8

  日期：1993.1

  A concise and practical total synthesis of (+/-)-triptoquinone A (1), a novel interleukin-1 inhibitor isolated from Tripterygium wilfordii var. regelii, has been achieved in 11 steps from the known naphthol 2.
• US5654343A
  申请人：——

  公开号：US5654343A

  公开（公告）日：1997-08-05
• 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.