(4aS,5R,6R,8aS)-5-[(2,5-dimethoxyphenyl)methyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-one | 237735-95-4

• 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: (4aS,5R,6R,8aS)-5-[(2,5-dimethoxyphenyl)methyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-one
• CAS: 237735-95-4
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: RJOQSNKLSLXHIN-SPPOGVHBSA-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：

  (4aS,5R,6R,8aS)-5-[(2,5-dimethoxyphenyl)methyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-one 在 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 13.0h， 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 palladium on activated charcoal 氨 、 氢气 、 4-甲基苯磺酸吡啶 、 lithium 、 三乙胺 作用下， 以 丙酮 为溶剂， 生成 (4aS,5R,6R,8aS)-5-[(2,5-dimethoxyphenyl)methyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Enantiospecific total synthesis of (+)- and (–)-avarone and -avarol

  摘要：

  Enantiopure avarol and its oxidized congener avarone are synthesized in both podal series from an optically pure Wieland-Miescher enone; preliminary results from biochemical studies are summarized.

  DOI：

  10.1039/cc9960002717

文献信息

• NOVEL USE OF SESQUITERPENE DERIVATIVE
  申请人：Kookmin University Industry Academy Cooperation Foundation

  公开号：EP3482750A1

  公开（公告）日：2019-05-15

  The present disclosure relates to a novel use of a sesquiterpene derivative, more particularly to a composition for preventing, improving or treating macular degeneration or macular edema caused by vascular leakage in the eye, the composition containing a sesquiterpene derivative compound represented by Chemical Formula 1 of the present disclosure or a pharmaceutically acceptable salt thereof as an active ingredient. Whereas the intraocular disease-related treating agents available in the market should be injected directly into the vitreous cavity, thus causing pain and side effects, the sesquiterpene derivative compound of the present disclosure is delivered to the target tissue (eye) via different administration routes (oral, intraperitoneal, etc.) other than the intravitreal route. Accordingly, the sesquiterpene derivative compound provides excellent therapeutic effect without being restricted by the administration routes.

  本公开涉及倍半萜衍生物的一种新用途，更具体地说，涉及一种用于预防、改善或治疗由眼部血管渗漏引起的黄斑变性或黄斑水肿的组合物，该组合物含有本公开化学式 1 所代表的倍半萜衍生物化合物或其药学上可接受的盐作为活性成分。市场上与眼内疾病相关的治疗药物应直接注射到玻璃体腔内，因此会引起疼痛和副作用，而本公开的倍半萜衍生物化合物可通过不同的给药途径（口服、腹腔注射等）给药到目标组织（眼睛），而非玻璃体腔内途径。因此，倍半萜衍生物化合物不受给药途径的限制，可提供极佳的治疗效果。
• Use of sesquiterpene derivative
  申请人：KOOKMIN UNIVERSITY INDUSTRY ACADEMY COOPERATION FOUNDATION

  公开号：US10918625B2

  公开（公告）日：2021-02-16

  The present disclosure relates to a novel use of a sesquiterpene derivative, more particularly to a composition for preventing, improving or treating macular degeneration or macular edema caused by vascular leakage in the eye, the composition containing a sesquiterpene derivative compound represented by Chemical Formula 1 of the present disclosure or a pharmaceutically acceptable salt thereof as an active ingredient. Whereas the intraocular disease-related treating agents available in the market should be injected directly into the vitreous cavity, thus causing pain and side effects, the sesquiterpene derivative compound of the present disclosure is delivered to the target tissue (eye) via different administration routes (oral, intraperitoneal, etc.) other than the intravitreal route. Accordingly, the sesquiterpene derivative compound provides excellent therapeutic effect without being restricted by the administration routes.

  本公开涉及倍半萜衍生物的一种新用途，更具体地说，涉及一种用于预防、改善或治疗由眼部血管渗漏引起的黄斑变性或黄斑水肿的组合物，该组合物含有本公开化学式 1 所代表的倍半萜衍生物化合物或其药学上可接受的盐作为活性成分。市场上与眼内疾病相关的治疗药物应直接注射到玻璃体腔内，因此会引起疼痛和副作用，而本公开的倍半萜衍生物化合物可通过不同的给药途径（口服、腹腔注射等）给药到目标组织（眼睛），而非玻璃体腔内途径。因此，倍半萜衍生物化合物不受给药途径的限制，可提供极佳的治疗效果。
• Enantiospecific total synthesis of (+)- and (–)-avarone and -avarol
  作者：Edward P. Locke、Sidney M. Hecht

  DOI：10.1039/cc9960002717

  日期：——

  Enantiopure avarol and its oxidized congener avarone are synthesized in both podal series from an optically pure Wieland-Miescher enone; preliminary results from biochemical studies are summarized.
• 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.