(4S,4aS,7S,8R,8aS)-8-hydroxy-4a-methyl-4-[(3S)-3-methyl-4-phenylmethoxybutanoyl]-7-propan-2-yl-1,3,4,5,6,7,8,8a-octahydronaphthalen-2-one | 160715-33-3

• 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: (4S,4aS,7S,8R,8aS)-8-hydroxy-4a-methyl-4-[(3S)-3-methyl-4-phenylmethoxybutanoyl]-7-propan-2-yl-1,3,4,5,6,7,8,8a-octahydronaphthalen-2-one
• CAS: 160715-33-3
• 化学式: C₂₆H₃₈O₄
• 分子量: 414.585
• InChiKey: MVNMWFNLSYNZLU-PLYFBUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,4aS,7S,8R,8aS)-8-hydroxy-4a-methyl-4-[(3S)-3-methyl-4-phenylmethoxybutanoyl]-7-propan-2-yl-1,3,4,5,6,7,8,8a-octahydronaphthalen-2-one 、 原甲酸三甲酯 在 acid 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以97%的产率得到(S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl)-3-methyl-butan-1-one
  参考文献：
  名称：

  查坦霉素的全合成。

  摘要：

  作为血小板活化因子的拮抗剂，从软珊瑚中分离出来的chatancin（1）具有潜在的治疗用途。第一全合成[等式。（1）]外消旋形式的这种结构上不常见的二萜与天然（+）-茶丹素和非天然（-）-茶丹素的正式总合成物一起进行了描述。

  DOI：

  10.1002/(sici)1521-3773(19980904)37:16<2226::aid-anie2226>3.0.co;2-h
• 作为产物：
  描述：

  百里醌 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 乙醇 、 三氟化硼乙醚 、 叔丁基锂 、 sodium 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 253.67h， 生成 (4S,4aS,7S,8R,8aS)-8-hydroxy-4a-methyl-4-[(3S)-3-methyl-4-phenylmethoxybutanoyl]-7-propan-2-yl-1,3,4,5,6,7,8,8a-octahydronaphthalen-2-one
  参考文献：
  名称：

  Versuche zur enantiomerenreinen Synthese des Chatancins, 1. Mitt. Synthese von (1R,2S,6S,7R,8S,3?S)-2-(4?-Benzyloxy-3?-methylbutoyl)-7-hydroxy-8-isopropyl-1-methylbicyclo [4.4.0]decan-4-on

  摘要：

  Our first target on the way towards the synthesis of enantiomerically pure chatancin is the preparation of the title compound. The cycloadduct of 5,5-dimethoxy- 1,2,3,4-tetrachlorocyclopentadiene and thymoquinone is stereo- and regioselectively reduced to the tricyclic ketoalcohol 4, which by nucleophilic cyclisation and reductive removal of the keto group as well as the chlorine atoms yielded a tetracyclic dimethoxyketal. Acidic hydrolysis freed the keto group, which now was treated with a chiral lithium alkyl compound derived from methyl (R)-2-methyl-3-hydroxypropionate in few steps. The resulting stereomeric tertiary alkohols were fragmented and the decalinones thus obtained separated. X-ray analysis permitted the determination of the absolute configuration of these decalinone derivatives.

  DOI：

  10.1007/bf00812715

文献信息

• Versuche zur enantiomerenreinen Synthese des Chatancins, 1. Mitt. Synthese von (1R,2S,6S,7R,8S,3?S)-2-(4?-Benzyloxy-3?-methylbutoyl)-7-hydroxy-8-isopropyl-1-methylbicyclo [4.4.0]decan-4-on
  作者：W. D. Aichberger、J. Aigner、E. G�ssinger、K. Gruber、G. Menz

  DOI：10.1007/bf00812715

  日期：——

  Our first target on the way towards the synthesis of enantiomerically pure chatancin is the preparation of the title compound. The cycloadduct of 5,5-dimethoxy- 1,2,3,4-tetrachlorocyclopentadiene and thymoquinone is stereo- and regioselectively reduced to the tricyclic ketoalcohol 4, which by nucleophilic cyclisation and reductive removal of the keto group as well as the chlorine atoms yielded a tetracyclic dimethoxyketal. Acidic hydrolysis freed the keto group, which now was treated with a chiral lithium alkyl compound derived from methyl (R)-2-methyl-3-hydroxypropionate in few steps. The resulting stereomeric tertiary alkohols were fragmented and the decalinones thus obtained separated. X-ray analysis permitted the determination of the absolute configuration of these decalinone derivatives.
• Total Synthesis of Chatancin
  作者：Josef Aigner、Edda Gössinger、Hanspeter Kählig、Georg Menz、Karin Pflugseder

  DOI：10.1002/(sici)1521-3773(19980904)37:16<2226::aid-anie2226>3.0.co;2-h

  日期：1998.9.4

  As an antagonist of the platelet activating factor, chatancin (1), which is isolated from a soft coral, is of potential therapeutic use. The first total synthesis [Eq. (1)] of this structurally unusual diterpene in racemic form is described along with the formal total syntheses of natural (+)-chatancin as well as unnatural (-)-chatancin.

  作为血小板活化因子的拮抗剂，从软珊瑚中分离出来的chatancin（1）具有潜在的治疗用途。第一全合成[等式。（1）]外消旋形式的这种结构上不常见的二萜与天然（+）-茶丹素和非天然（-）-茶丹素的正式总合成物一起进行了描述。