cis-1α-[(2,5-dimethoxyphenyl)methyl]-octahydro-1β,2α,4aα-trimethyl-5(6H)-naphthalenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-1α-[(2,5-dimethoxyphenyl)methyl]-octahydro-1β,2α,4aα-trimethyl-5(6H)-naphthalenone
• 英文别名: (4aS,5R,6R,8aR)-5-[(2,5-dimethoxyphenyl)methyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-one
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: RJOQSNKLSLXHIN-BDRMCPCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  cis-1α-[(2,5-dimethoxyphenyl)methyl]-octahydro-1β,2α,4aα-trimethyl-5(6H)-naphthalenone 在 ammonium cerium(IV) nitrate 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 2-((1R,2R,4aR,8aS)-1,2,4a-Trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-[1,4]benzoquinone
  参考文献：
  名称：

  Synthesis of a Potential Key Intermediate of Akaterpin, Specific Inhibitor of PI-PLC

  摘要：

  In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and tuans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of beta,gamma-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00619-0
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基苯 在 三乙基硅烷 、 palladium dihydroxide 、 氢氟酸 、 氢气 、 sodium hexamethyldisilazane 、 magnesium 、 1,2-二溴乙烷 、 三乙胺 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 68.33h， 生成 cis-1α-[(2,5-dimethoxyphenyl)methyl]-octahydro-1β,2α,4aα-trimethyl-5(6H)-naphthalenone
  参考文献：
  名称：

  Synthesis of a Potential Key Intermediate of Akaterpin, Specific Inhibitor of PI-PLC

  摘要：

  In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and tuans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of beta,gamma-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00619-0

文献信息

• Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone
  作者：Nobuyuki Kawai、Ken-ichi Takao、Susumu Kobayashi

  DOI：10.1016/s0040-4039(99)00686-3

  日期：1999.5

  In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, synthesis of cis-decalin 2 and trans-decalin 3 was carried out. Comparison of NMR spectra of 2 and 3 with that of akaterpin indicated that the upper decalin has a cis-fused structure. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of a Potential Key Intermediate of Akaterpin, Specific Inhibitor of PI-PLC
  作者：Nobuyuki Kawai、Yuko Fujibayashi、Seiya Kuwabara、Ken-ichi Takao、Yasuharu Ijuin、Susumu Kobayashi

  DOI：10.1016/s0040-4020(00)00619-0

  日期：2000.8

  In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and tuans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of beta,gamma-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd. All rights reserved.