(3aR,4R,5R,6aS)-benzoic acid 4-[(1E)-3-hydroxy-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester | 1010074-85-7

• 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: (3aR,4R,5R,6aS)-benzoic acid 4-[(1E)-3-hydroxy-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• 英文别名: [3aR-[3aα,4α(E),5β,6aα]]-5-(benzoyloxy)hexahydro-4-(3-hydroxy-1-octenyl)-2H-cyclopenta[b]furan-2-one；[(3aR,4R,5R,6aS)-4-[(E)-3-hydroxyoct-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• CAS: 1010074-85-7
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: FKTNHWPVYLAIRZ-CJWDIAKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6aS)-benzoic acid 4-[(1E)-3-hydroxy-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 在 咪唑 、 4-二甲氨基吡啶 、 三丁基膦 、 氢氟酸 、 potassium tert-butylate 、 双氧水 、 二异丁基氢化铝 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 135.75h， 生成 前列腺素 J2
  参考文献：
  名称：

  First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J₂

  摘要：

  Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.

  DOI：

  10.1021/jo034502h
• 作为产物：
  描述：

  [3aR(3aα,4α,5β,6aα)]-(-)-5-(苯甲酰氧基)六氢-2-氧代-2H-环戊并[b]呋喃-4-甲醛 在 乙醇 、 (-)-(S)-BINAL-H 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (3aR,4R,5R,6aS)-benzoic acid 4-[(1E)-3-hydroxy-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
  参考文献：
  名称：

  First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J₂

  摘要：

  Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.

  DOI：

  10.1021/jo034502h

文献信息

• Process and intermediates to prepare latanoprost
  申请人：——

  公开号：US20030045571A1

  公开（公告）日：2003-03-06

  The present invention is a novel intermediate, compound of the formula (VI) 1 and salts thereof. In addition, the invention includes a process for the preparation of a 15(S)-prostaglandin intermediates compounds (IV) and (XVIII) which comprises (1) contacting a the corresponding enone with (-)-chlorodiisopinocampheylborane while maintaining the reaction mixture temperature in the range of from about −50° to about 0° and (2) contacting the reaction mixture of step ( 1 ) with a boron complexing agent.

  本发明是一种新型中间体，其化合物公式为（VI）1及其盐。此外，该发明还包括一种制备15(S)-前列腺素中间体化合物（IV）和（XVIII）的方法，包括（1）将相应的烯酮与(-)-氯异萜基硼烷反应，同时保持反应混合物的温度在约-50°至约0°范围内，以及（2）将步骤（1）中的反应混合物与硼络合剂接触。
• [EN] PROCESS AND INTERMEDIATES TO PREPARE LATANOPROST<br/>[FR] PROCEDE ET INTERMEDIAIRES POUR PREPARER DU LATANOPROST
  申请人：UPJOHN CO

  公开号：WO2001087816A1

  公开（公告）日：2001-11-22

  The present invention is a intermediate, compound of formula (VI) and salts thereof. In addition, the invention includes a process for the preparation of a 15(S)-prostaglandin intermediates which comprises (1) contacting enones with (+)-chlorodiisopinocampheylborane while maintaining the reaction mixture temperature in the range of from about -50° to about 0° and (2) contacting the reaction mixture of step (1) with a boron complexing agent.

  本发明涉及一种公式（VI）的中间体化合物及其盐。此外，本发明还包括一种制备15（S）-前列腺素中间体的过程，其包括（1）在保持反应混合物温度在约-50℃至约0℃范围内的情况下，将烯酮与(+)-氯代异蒎基硼烷接触，以及（2）将步骤（1）的反应混合物与硼络合剂接触。
• PROCESS AND INTERMEDIATES TO PREPARE LATANOPROST
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1406854A1

  公开（公告）日：2004-04-14
• US6689901B2
  申请人：——

  公开号：US6689901B2

  公开（公告）日：2004-02-10
• [EN] PROCESS AND INTERMEDIATES TO PREPARE LATANOPROST<br/>[FR] PROCEDE ET PRODUITS INTERMEDIAIRES UTILISES POUR PRODUIRE DU LATANOPROST
  申请人：UPJOHN CO

  公开号：WO2003008368A1

  公开（公告）日：2003-01-30

  The present invention is a novel intermediate, compound of the formula (VI), and salts thereof. In addition, the invention includes a process for the preparation of a 15(S)-prostaglandin intermediates compounds (IV) and (XVIII) which comprises (1) contacting the corresponding enone with (-)-chlorodiisopinocampheylborane while maintaining the reaction mixture temperature in the range of from about -50° to about 0° and (2) contacting the reaction mixture of step (1) with a boron complexing agent.