(1R,2R,3R,5S,6S,7S)-3-acetoxy-1,7,8,9-tetrachloro-10,10-dimethoxy-5-(tert-butyldimethylsiloxy)tricyclo[5.2.1.02,6]dec-8-ene | 949585-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3R,5S,6S,7S)-3-acetoxy-1,7,8,9-tetrachloro-10,10-dimethoxy-5-(tert-butyldimethylsiloxy)tricyclo[5.2.1.02,6]dec-8-ene
• 英文别名: (1R,2R,3R,5S,6S,7S)-3-acetoxy-1,7,8,9-tetrachloro-10,10-dimethoxy-5-(tert-butyldimethylsiloxy)tricyclo[5.2.1.0^2,6]dec-8-ene
• CAS: 949585-38-0
• 化学式: C₂₀H₃₀Cl₄O₅Si
• 分子量: 520.353
• InChiKey: XXMNBMQULIYREY-MQOWNXBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5S,6S,7S)-3-acetoxy-1,7,8,9-tetrachloro-10,10-dimethoxy-5-(tert-butyldimethylsiloxy)tricyclo[5.2.1.02,6]dec-8-ene 在 jones' reagent 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 溶剂黄146 、 丙酮 为溶剂， 反应 1.5h， 生成 (3aS,4R,7S,7aS)-4,5,6,7-Tetrachloro-8,8-dimethoxy-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one
  参考文献：
  名称：

  Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 2: EPC-synthesis of the hydrindene subunit of the macquarimicins

  摘要：

  The EPC-synthesis of the cis- hydrindene subunit of the macquarimicins, antibiotics with antitumour and anti-inflammatory activity, has been achieved. Desymmetrization of cis-1,4-cyclopent-2-enediol was succeeded by Diels-Alder reaction and functional group transformations to a tricyclic ketone. Regio- and stereoselective methylation via Claisen condensation and hydrogenation was followed by nucleophilic, intramolecular addition, reduction and acidic fragmentation. Further functional group transformations led to the target molecule. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.094
• 作为产物：
  描述：

  5,5-二甲氧基-1,2,3,4-四氯环戊二烯 、 Acetic acid 4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester 在 4 A molecular sieve 、 对苯二酚 作用下， 以 xylene 为溶剂， 反应 144.0h， 以81%的产率得到(1R,2R,3R,5S,6S,7S)-3-acetoxy-1,7,8,9-tetrachloro-10,10-dimethoxy-5-(tert-butyldimethylsiloxy)tricyclo[5.2.1.02,6]dec-8-ene
  参考文献：
  名称：

  Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 2: EPC-synthesis of the hydrindene subunit of the macquarimicins

  摘要：

  The EPC-synthesis of the cis- hydrindene subunit of the macquarimicins, antibiotics with antitumour and anti-inflammatory activity, has been achieved. Desymmetrization of cis-1,4-cyclopent-2-enediol was succeeded by Diels-Alder reaction and functional group transformations to a tricyclic ketone. Regio- and stereoselective methylation via Claisen condensation and hydrogenation was followed by nucleophilic, intramolecular addition, reduction and acidic fragmentation. Further functional group transformations led to the target molecule. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.094