(3'R,4'R,4'aS,8'aS)-4'-[(2,5-dimethoxyphenyl)methyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene] | 237735-94-3

• 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: (3'R,4'R,4'aS,8'aS)-4'-[(2,5-dimethoxyphenyl)methyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene]
• CAS: 237735-94-3
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: SOCXOTPRYWLSOG-WIQPIVSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3'R,4'R,4'aS,8'aS)-4'-[(2,5-dimethoxyphenyl)methyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene] 在 盐酸 、 sodium dithionite 、 ammonium cerium(IV) nitrate 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 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
• 作为产物：
  描述：

  (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 在 镍 正丁基锂 、 氨 、 氢气 、 lithium 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 37.0h， 生成 (3'R,4'R,4'aS,8'aS)-4'-[(2,5-dimethoxyphenyl)methyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene]
  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.