[1S-[1α,2β,3β(S*),4α]]-7-[3-[(2-oxo-4-phenyl-3-oxazolidinyl)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptynoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [1S-[1α,2β,3β(S*),4α]]-7-[3-[(2-oxo-4-phenyl-3-oxazolidinyl)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptynoic acid
• 英文别名: 7-[(1S,2S,3S,4R)-3-[(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)methyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-ynoic acid
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: SKEKHZPCXUFVSM-SPYJTGKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1S-[1α,2β,3β(S*),4α]]-7-[3-[(2-oxo-4-phenyl-3-oxazolidinyl)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptynoic acid 生成 (Z)-7-[(1S,2S,3S,4R)-3-[(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)methyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid
  参考文献：
  名称：

  THOTTATHIL, JOHN K.

  摘要：

  DOI：
• 作为产物：
  描述：

  [(1S,2R,3S,4R)-3-[(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)methyl]-7-oxabicyclo[2.2.1]heptan-2-yl]methyl 4-methylbenzenesulfonate 、 5-己炔酸 生成 [1S-[1α,2β,3β(S*),4α]]-7-[3-[(2-oxo-4-phenyl-3-oxazolidinyl)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptynoic acid
  参考文献：
  名称：

  THOTTATHIL, JOHN K.

  摘要：

  DOI：

文献信息

• Process for preparing 7-oxabicycloheptane amino-alcohol intermediates
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04687865A1

  公开（公告）日：1987-08-18

  A process is provided for preparing a 7-oxabicycloheptane amino alcohol intermediate of the general structure ##STR1## (wherein the above structures represents (D) or (L) isomers) which is useful in preparing thromboxane A.sub.2 receptor antagonists. This intermediate is prepared by reacting mesoanhydride with an aryl amine ##STR2## wherein R is alkyl, CH.sub.2 OH, CO.sub.2 H or CO.sub.2 alkyl, to form the acid ##STR3## which is reduced by treatment with lithium aluminum hydride or diisobutylaluminum hydride or Red-Al to form the alcohol ##STR4## wherein R.sup.1 is CH.sub.2 OH when R is CO.sub.2 H, CO.sub.2 alkyl or CH.sub.2 OH, and R.sup.1 is alkyl when R is alkyl; where in the above alcohol R.sup.1 is CH.sub.2 OH, such alcohol compound is treated with an alkyl chloroformate in the presence of base such as an alkali metal alkoxide to form the alcohol ##STR5## which undergoes cleavage by treatment with alkali metal, ammonia and acid to form the amino alcohol intermediate. Where in the above alcohol R.sup.1 is alkyl, that is ##STR6## such alcohol may be hydrogenated to form the aminoalcohol intermediate. All of the above 7-oxabicycloheptane compounds are novel and also form part of the present invention.

  提供了一种制备一种7-氧杂双环庚烷氨基醇中间体的过程，其具有以下一般结构##STR1##（其中上述结构代表（D）或（L）异构体），该中间体在制备血栓素A.sub.2受体拮抗剂时很有用。该中间体通过将脱水苹果酸酐与芳基胺##STR2##反应制备，其中R为烷基，CH.sub.2 OH，CO.sub.2 H或CO.sub.2烷基，形成酸##STR3##，通过用氢化铝锂或二异丁基铝锂或Red-Al处理以还原该酸，形成醇##STR4##，其中当R为CO.sub.2 H，CO.sub.2烷基或CH.sub.2 OH时，R.sup.1为CH.sub.2 OH，当R为烷基时，R.sup.1为烷基；在上述醇中，R.sup.1为CH.sub.2 OH，这种醇化合物在碱金属烷氧化物等碱存在下与烷基氯甲酸酯反应，形成醇##STR5##，经由碱金属、氨和酸处理进行解离，形成氨基醇中间体。在上述醇中，R.sup.1为烷基，即##STR6##，这种醇可以被氢化以形成氨基醇中间体。所有上述的7-氧杂双环庚烷化合物都是新颖的，也是本发明的一部分。
• THOTTATHIL, JOHN K.
  作者：THOTTATHIL, JOHN K.

  DOI：——

  日期：——