(1S,2S,3R,4R,6S,7R)-1,7,8,9-tetrachloro-10,10-dimethoxy-4-methyltricyclo[5.2.1.0^2,6]dec-8-en-3-ol | 949585-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R,4R,6S,7R)-1,7,8,9-tetrachloro-10,10-dimethoxy-4-methyltricyclo[5.2.1.0^2,6]dec-8-en-3-ol
• CAS: 949585-54-0
• 化学式: C₁₃H₁₆Cl₄O₃
• 分子量: 362.08
• InChiKey: IUOLOQCFDPOABZ-XBBVGTPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R,6S,7R)-1,7,8,9-tetrachloro-10,10-dimethoxy-4-methyltricyclo[5.2.1.0^2,6]dec-8-en-3-ol 在 盐酸 、 sodium 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 生成 (1S,2S,6S,7R,8R)-7-hydroxy-8-methyl-4-oxobicyclo[4.3.0]non-2-yl-carboxylic acid
  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：

  Acetic acid 4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester 在 palladium on activated charcoal 、 platinum on activated charcoal sodium tetrahydroborate 、 jones' reagent 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 原甲酸三乙酯 、 对苯二酚 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 丙酮 、 xylene 为溶剂， 115.0 ℃ 、101.33 kPa 条件下， 反应 172.83h， 生成 (1S,2S,3R,4R,6S,7R)-1,7,8,9-tetrachloro-10,10-dimethoxy-4-methyltricyclo[5.2.1.0^2,6]dec-8-en-3-ol
  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