(1S,2R,4aS,5R,8R,8aR)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate | 745066-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,4aS,5R,8R,8aR)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate
• 英文别名: sequiterpene；(1S,2R,4aR,5R,8R,8aR)-1,8a-dihydroxy-2-acetoxy-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene；1,8a-dihydroxy-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate；acetic acid 1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl ester；(1S,2R,4aR,5R,8R,8aR)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-2-naphtalenyl acetate；sesquiterpene；[(1S,2R,4aR,5R,8R,8aR)-1,8a-dihydroxy-3,8-dimethyl-5-prop-1-en-2-yl-2,4a,5,6,7,8-hexahydro-1H-naphthalen-2-yl] acetate
• CAS: 745066-65-3
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: RXHIKAIVEMAPRU-JRIGQVHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,4aS,5R,8R,8aR)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate 、 tert-butyl (1R,10R,12S)-6-chloro-8-methyl-13-oxo-9,14-dioxa-8,11-diazatetracyclo[10.2.1.01,10.02,7]pentadeca-2(7),3,5-triene-11-carboxylate 在 potassium tert-butylate 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 3.0h， 以57%的产率得到CJ-12662
  参考文献：
  名称：

  Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662

  摘要：

  The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.

  DOI：

  10.1021/jo048711t
• 作为产物：
  描述：

  甲醇 、 CJ-12662 在 三乙胺 作用下， 反应 72.0h， 生成 methyl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydro-4-oxa-3,5-diazacyclopenta[a]naphthalene-2-carboxylate 、 (1S,2R,4aS,5R,8R,8aR)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate
  参考文献：
  名称：

  [EN] ANTIPARASITIC TERPENE ALKALOIDS
  [FR] TERPENE ALCALOIDES ANTIPARASITIQUES

  摘要：

  公开号：

  WO2004072086A3

文献信息

• [EN] ANTIPARASITIC TERPENE ALKALOIDS<br/>[FR] TERPENE ALCALOIDES ANTIPARASITIQUES
  申请人：PFIZER LTD

  公开号：WO2004072086A3

  公开（公告）日：2004-10-07
• Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662
  作者：Charles Didier、Douglas J. Critcher、Nigel D. Walshe、Yasuhiro Kojima、Yuji Yamauchi、Anthony G. M. Barrett

  DOI：10.1021/jo048711t

  日期：2004.11.1

  The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.