(3aR,4R,5R,6aS)-5-(苯甲酰氧基)六氢-4-[(1E)-3-氧代-5-苯基-1-戊烯基]-2H-环戊并[b]呋喃-2-酮 | 55076-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3aR,4R,5R,6aS)-5-(苯甲酰氧基)六氢-4-[(1E)-3-氧代-5-苯基-1-戊烯基]-2H-环戊并[b]呋喃-2-酮
• 中文别名: (3Ar,4r,5r,6as)-5-(苯甲酰基氧基)六氢-4-[(1e)-3-氧代-5-苯基-1-戊烯yl]-2H-环戊并[b]呋喃-2-酮；(3aR,4R,5R,6aS)-2H-环戊并[b]呋喃-2-酮,5-(苯甲酰氧基)六氢-4-[(1E)-3-氧代-5-苯基-1-戊烯-1-基]-；(3AR,4R,5R,6AS)-5-(苯甲酰氧基)六氢-4-[(1E)-3-氧代-5-苯基-1-戊烯基]-2H-环戊并[B]呋喃-2-酮
• 英文名称: (3aR,4R,5R,6aS)-2-oxo-4-((1E)-3-oxo-5-phenylpent-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate
• 英文别名: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((1E)-3-oxo-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one；[3aR-[3aα,4α(E),5β,6aα]]-5-(benzoyloxy)hexahydro-4-(3-oxo-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one；[3aR-(3aα,4α,5α,6aα)]-hexahydro-2-oxo-4-(5-phenyl-3-oxopent-1-enyl)-5-benzoyloxy-2H-cyclopenta[b]furane；(1S,5R,6R,7R)-6-[(E)-3-Oxo-5-phenyl-1-pentenyl]-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one；[3aR-(3aα,4α,5α,6aα)]-hexahydro-2-oxo-4-(5-phenyl-3-oxopent-1-enyl)-5-benzoyloxy-2H-cyclopenta[b]furan；benzoic acid (3aR,4R,5R,6aS)-2-oxo-4((E)-3-oxo-5-phenyl-pent-1-enyl)-hexahydro-cyclopenta[b]furan-5-yl ester；(3aR,4R,5R,6aS)-4-[3-oxo-5-phenyl-1E-pentenyl]-5-(benzoyloxy)-hexahydro-2H-cyclopenta[b]furan-2-one；(3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate；[(3aR,4R,5R,6aS)-2-oxo-4-[(E)-3-oxo-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• CAS: 55076-60-3
• 化学式: C₂₅H₂₄O₅
• 分子量: 404.463
• InChiKey: XMDHRDDKCRNISB-ZTWUSJMCSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  606.9±55.0 °C(Predicted)
• 密度：
  1.25

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：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6aS)-5-(苯甲酰氧基)六氢-4-[(1E)-3-氧代-5-苯基-1-戊烯基]-2H-环戊并[b]呋喃-2-酮 在 potassium tert-butylate 、 二异丁基氢化铝 、 potassium carbonate 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.67h， 生成 比马前列素
  参考文献：
  名称：

  KR2017/25682

  摘要：

  公开号：
• 作为产物：
  描述：

  3-苯丙酸甲酯 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 (3aR,4R,5R,6aS)-5-(苯甲酰氧基)六氢-4-[(1E)-3-氧代-5-苯基-1-戊烯基]-2H-环戊并[b]呋喃-2-酮
  参考文献：
  名称：

  Synthesis and in vitro evaluation of human FP-receptor selective prostaglandin analogues

  摘要：

  The in vitro evaluation of a series of saturated prostaglandins revealed that compounds with omega chain aromatic rings retain nanomolar potency for the human prostaglandin F receptor (hFP receptor), exemplified by compound 8. In contrast, the double bonds are required for activity in the series with an acyclic omega chain as in PGF(2 alpha). (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00273-0

文献信息

• Method for preparing prostaglandin derivative
  申请人：Daiichi Fine Chemical Co., Ltd.

  公开号：EP1886992A1

  公开（公告）日：2008-02-13

  A method for preparing a prostaglandin derivative represented by the following general formula (I): (wherein Ph represents phenyl group, R1 represents a C1-7 alkyl group, a C1-7 alkenyl group, phenyl group, or benzyl group), which comprises the successive steps (1) to (8) described in the specification, or any one step or two or more successive steps selected from the group consisting of the steps (1) to (8). A method for efficiently, inexpensively and safely preparing prostaglandin derivatives, of which typical example is latanoprost, is provided.

  一种用以下一般式(I)代表的前列腺素衍生物的制备方法：（其中Ph代表苯基，R1代表C1-7烷基，C1-7烯基，苯基或苄基），其中包括在说明书中描述的连续步骤（1）至（8），或者从步骤（1）至（8）组成的步骤中选择的一个步骤，或者选择两个或更多连续步骤。提供了一种高效、廉价和安全地制备前列腺素衍生物的方法，其中典型示例是拉唑前列酮。
• Improved Process for the Production of Prostaglandins and Prostaglandin Analogs
  申请人：SANDOZ AG

  公开号：EP2143712A1

  公开（公告）日：2010-01-13

  The present invention relates to an improved process for the production of prostaglandins and prostaglandin analogs. In particular, this invention relates to the production of prostaglandins of the PGF2α-series, including latanoprost, travoprost, and bimatoprost, which are active pharmaceutical ingredients used for the reduction of elevated intraocular pressure in patients with glaucoma and ocular hypertension.

  本发明涉及一种改进的用于生产前列腺素和前列腺素类似物的过程。具体而言，本发明涉及PGF2α系列前列腺素的生产，包括拉坦前列醇、曲普前列醇和比马前列醇，这些是用于降低青光眼和眼内高压患者眼内压的活性药用成分。
• [EN] PROCESS FOR THE PREPARATION OF F-SERIES PROSTAGLANDINS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PROSTAGLANDINES DE LA SÉRIE F
  申请人：CAYMAN CHEM CO

  公开号：WO2011046569A1

  公开（公告）日：2011-04-21

  A process for the synthesis and purification of F-series prostaglandin compounds and synthetic intermediates used to prepare them. The synthetic intermediates are solid and may be purified by precipitation and therefore may form the representative F-series prostaglandin compounds such as latanoprost, bimatoprost, fluprostenol, cloprostenol, and substituted analogs therefrom in highly pure forms.

  用于合成和纯化F系列前列腺素化合物和用于制备它们的合成中间体的过程。这些合成中间体是固体，可以通过沉淀纯化，因此可以形成代表性的F系列前列腺素化合物，如拉他诺前列醇、比马前列醇、氟前列醇、克洛前列醇以及其高度纯净的取代物。
• METHOD FOR PREPARING PROSTAGLANDIN DERIVATIVE
  申请人：MURATA Noriaki

  公开号：US20080033176A1

  公开（公告）日：2008-02-07

  A method for preparing a prostaglandin derivative represented by the following general formula (I): (wherein Ph represents phenyl group, R 1 represents a C 1-7 alkyl group, a C 1-7 alkenyl group, phenyl group, or benzyl group), which comprises the successive steps (1) to (8) described in the specification, or any one step or two or more successive steps selected from the group consisting of the steps (1) to (8). A method for efficiently, inexpensively and safely preparing prostaglandin derivatives, of which typical example is latanoprost, is provided.

  一种用以下一般式(I)表示的前列腺素衍生物的制备方法：（其中Ph代表苯基，R1代表C1-7烷基，C1-7烯基，苯基或苄基），该方法包括规范中描述的连续步骤（1）至（8），或者从步骤（1）至（8）中选择的任一步骤或两个或更多连续步骤。提供了一种高效、廉价和安全制备前列腺素衍生物的方法，其中典型示例是拉唑前列醇。
• Process and intermediates to prepare latanoprost
  申请人：——

  公开号：US20030187071A1

  公开（公告）日：2003-10-02

  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 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，化合物的式子为(VI)1及其盐。此外，本发明还包括一种制备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(-)-氯二异丙基萜烯硼烷接触，同时将反应混合物温度保持在约-50℃至约0℃的范围内，以及(2)将步骤(1)的反应混合物与硼络合剂接触。