2-[[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol | 237735-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol
• CAS: 237735-97-6
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: FBMAHDGTCDISLJ-NMSZZDKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol 在 pyridine-SO3 complex 、 sodium carbonate 作用下， 以61%的产率得到
  参考文献：
  名称：

  Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(99)00686-3
• 作为产物：
  描述：

  (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 在 镍 盐酸 、 正丁基锂 、 sodium dithionite 、 ammonium cerium(IV) nitrate 、 氨 、 氢气 、 四氯化钛 、 lithium 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 51.0h， 生成 2-[[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol
  参考文献：
  名称：

  Synthetic study of akaterpin: Determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(99)00686-3

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.