4-hydroxy-2-(7-hydroxyheptyl)-cyclopent-2-en-1-one | 64831-06-7

• 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: 4-hydroxy-2-(7-hydroxyheptyl)-cyclopent-2-en-1-one
• 英文别名: 2-(7-hydroxyheptyl)-4R-hydroxycyclopent-2-enone；4R-hydroxy-2-[7-hydroxyheptyl]-2-cyclopenten-1-one；7-(3R-Hydroxy-5-oxocyclopent-1-enyl)-heptan-1-ol；4-Hydroxy-2-(7-hydroxyheptyl)cyclopent-2-EN-1-one
• CAS: 64831-06-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: IUWYHMZSXNYIPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-(7-hydroxyheptyl)-cyclopent-2-en-1-one 在 2-甲基苯磺酸 作用下， 生成 (4R)-4-(tetrahydropyran-2-yloxy)-2-<7-(tetrahydropyran-2-yloxy)heptyl>cyclopent-2-enone
  参考文献：
  名称：

  Cyclobutyl substituted derivatives of prostaglandin analogs

  摘要：

  新型C15环丁基类前列腺素的衍生物或类似物在调节平滑肌活动方面具有用途。这些化合物具有宝贵的药理特性，如抗血小板聚集剂、胃抗分泌剂和支气管扩张剂。

  公开号：

  US04220795A1
• 作为产物：
  描述：

  壬二酸氢甲酯 在 W-2-Raney nickel Rexyn 300,mixed acid-base ion exchanger resin 、 Rexyn 300 、 硼酸 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 18.0h， 生成 4-hydroxy-2-(7-hydroxyheptyl)-cyclopent-2-en-1-one
  参考文献：
  名称：

  A short synthesis of γ-hydroxycyclopentemones

  摘要：

  DOI：

  10.1016/s0040-4039(00)86008-6

文献信息

• Process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS
  申请人：Miles Laboratories, Inc.

  公开号：US04159998A1

  公开（公告）日：1979-07-03

  Disclosed is an improved process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS -hydroxy-cyclopent-2-enone corresponding to the formula ##STR1## wherein m is an integer from 2 to 4. The compounds prepared by this process are useful as precursors in the preparation of carbinol PGE.sub.1 analogues having utility as bronchodilators and inhibitors of gastric secretion.

  本文揭示了一种改进的制备过程，用于制备与公式##STR1##相对应的2-(7-羟基烷基)-4R、4S或4RS-羟基环戊-2-烯酮，其中m是从2到4的整数。通过这个过程制备的化合物可用作合成卡比诺前列腺素E1类似物的前体，具有作为支气管扩张剂和胃分泌抑制剂的用途。
• 16-Hydroxy-16-vinyl (or cyclopropyl)-prostan-1-ols and pharmaceutical compositions containing the same
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0013107A1

  公开（公告）日：1980-07-09

  There are disclosed novel 15-deoxy-16-hydroxy-16- substituted prostanoic acid analogs in which the C-1 carboxyl is replaced by a primary alcohol and carboxylic acid esters, carbonates and carbamates thereof, and which have utility as bronchodilators, as hypotensive agents, and as agents forthe control of excessive gastric secretion. The novel compounds are represented by the formula: wherein Q is a divalent cyclopentyl moiety selected from the group consisting of: wherein R/ is an alkyl (C3-C7) optionally substituted with one or more alkyl groups of one to three carbon atoms; R2 is selected from the group hydroxyl, alkoxyl, alkanoyloxy, a protecting group such as tetrahydropyran-2-yl-oxy, triloweralkylsilyloxy; or alkoxyalkoxy such as wherein R' is hydrogen or alkyl (C1-C4) and R" is alkyl (C1-C4); X is the divalent radical wherein R3 is selected from the group vinyl and cyclopropyl; Z is selected from the group -(CH2)4, cis and and W is selected from the group consisting of -(CH2)3 OH and wherein R4 is selected from the group alkyl (C,-C.); alkoxy (C1-C4); dialkylamino (C1-C4); phenyl and phenyl substituted with one or more substituents selected from the group consisting of hydrogen, hydroxyl, lower alkyl, lower alkoxy, loweralkylthia, fluoride or chloride, wherein lower alkyl is C1-C4; The formula above embraces the optical isomers, racemic or other mixtures of these isomers and the mirror images thereof

  公开了新型 15-脱氧-16-羟基-16-取代的前列酸类似物，其中 C-1 羧基被伯醇及其羧酸酯、碳酸酯和氨基甲酸酯取代，可用作支气管扩张剂、降压药和控制胃分泌过多的药物。这些新型化合物由式表示： 其中 Q 是二价环戊基，选自由以下组成的组： 其中 R/ 是任选被一个或多个一至三个碳原子的烷基取代的烷基（C3-C7）；R2 选自羟基、烷氧基、烷酰氧基、保护基团如四氢吡喃-2-基氧基、三烷基硅氧基；或烷氧基烷氧基，如 其中 R' 为氢或烷基（C1-C4），R" 为烷基（C1-C4）； X 为二价基 其中 R3 选自乙烯基和环丙基组； Z 选自-(CH2)4 组，顺式和逆式。 和 W 选自-(CH2)3 OH 和-(CH2)4-OH 所组成的组。 其中 R4 选自烷基（C,-C.）；烷氧基（C1-C4）；二烷基氨基（C1-C4）；苯基和被一个或多个取代基取代的苯基，取代基选自氢、羟基、低级烷基、低级烷氧基、低级烷硫基、氟化物或氯化物组成的组，其中低级烷基为 C1-C4； 上式包括这些异构体的光学异构体、外消旋体或其他混合物及其镜像。
• Novel cyclopentenone derivatives and methods for the preparation of the novel compounds
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0043479A1

  公开（公告）日：1982-01-13

  Cyclopentenone compounds of formula I useful as intermediates in the preparation of certain substituted prostan-1-ols: wherein Z is and both R groups are the same and are hydrogen or the group: wherein R2 is (C1-C4) alkyl and R3 is hydrogen or (C1-C4) alkyl, with the proviso that Z is not -(CH2)4- when R is hydrogen. Processes for their preparation: by rearranging a substituted 2,5-dihydrofuran derivative of the formula: or by etherification of both OH functions in formula I with a 2-alkoxypropene of the formula

  式 I 的环戊烯酮化合物，可用作制备某些取代的原烷-1-醇的中间体： 其中 Z 是 且两个 R 基团相同，均为氢或基团： 其中 R2 是（C1-C4）烷基，R3 是氢或（C1-C4）烷基，但当 R 是氢时，Z 不是-(CH2)4-。 其制备方法：通过重新排列式 2，5-二氢呋喃的取代衍生物： 或将式 I 中的两个羟基官能团与式 2-烷氧基丙烯进行醚化反应
• Enol acylate analogs of E1 and E2 prostaglandins
  申请人：MILES LABORATORIES, INC.

  公开号：EP0073397A1

  公开（公告）日：1983-03-09

  Disclosed are C-9 enol acylate analogs of E1 and E2 prostaglandins which are variously useful as bronchodilators, gastric anti-secretory agents and cytoprotective agents.

  所公开的是 E1 和 E2 前列腺素的 C-9 烯醇酰基类似物，它们可用作支气管扩张剂、胃抗分泌剂和细胞保护剂。
• Esterase gene and its use
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0845534A2

  公开（公告）日：1998-06-03

  Described is a gene coding for an esterase capable of causing asymmetric hydrolysis of an organic carboxylic acid ester of a cyclopentenolone of formula I: wherein R1 is hydrogen or methyl, and R2 is C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C4 haloalkyl, a C5-C9 aliphatic hydrocarbon moiety which may be optionally protected on the terminal hydroxyl group thereof, or a C5-C9 fatty acid residue which may be optionally protected on the terminal carboxyl group thereof, to produce the cyclopentenolone of formula I in (R)-form, an esterase encoded by said gene as well as methods for its production and its use for the industrially favorable production of optically active cyclopentenolones of formula I which serve as the intermediates of drugs, agricultural chemicals, insecticides or other active products.

  所描述的是一种酯酶的编码基因，这种酯酶能使式 I 的环戊烯酮的有机羧酸酯发生不对称水解： 其中 R1 是氢或甲基，R2 是 C1-C10 烷基、C2-C10 烯基、C2-C10 炔基、C1-C4 卤代烷基、C5-C9 脂肪族烃基（其末端羟基可选择受保护）或 C5-C9 脂肪酸残基（其末端羧基可选择受保护）、生产(R)形式的式 I 环戊烯酮的上述基因编码的酯酶及其生产方法，以及将其用于工业化生产具有光学活性的式 I 环戊烯酮（可用作药物、农药、杀虫剂或其他活性产品的中间体）的方法。