cis-cyclopent-1,3-diyl diacetate | 183795-67-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-cyclopent-1,3-diyl diacetate
• 英文别名: cis-Cyclopentan-1,3-dioldiacetat；cis-1,3-diacetoxy-cyclopentane；cis-1,3-Diacetoxy-cyclopentan；Cis-(+)-1,3-Cyclopentanediol diacetate；[(1S,3R)-3-acetyloxycyclopentyl] acetate
• CAS: 183795-67-7
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: XCFPBHDEAZTCJS-DTORHVGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-cyclopent-1,3-diyl diacetate 在 sodium dihydrogenphosphate 、 sodium azide 、 Electrophorus electricus acetylcholinesterase 作用下， 生成 (1R,3S)-(-)-3-hydroxycyclopentyl acetate 、 (1S,3R)-(+)-3-hydroxycyclopentyl acetate
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0
• 作为产物：
  描述：

  Cis-3,5-二乙酰氧基-1-环戊烯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 cis-cyclopent-1,3-diyl diacetate
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0

文献信息

• 770. Alicyclic glycols. Part VI. Derivatives of cyclopentane-1 : 2-diol
  作者：L. N. Owen、Peter N. Smith

  DOI：10.1039/jr9520004026

  日期：——
• [EN] AROMATIC HYDROXYETHERS<br/>[FR] HYDROXYETHERS AROMATIQUES
  申请人：RHONE-POULENC RORER LIMITED

  公开号：WO1996031476A1

  公开（公告）日：1996-10-10

  (EN) This invention is directed to physiologically active compounds of formula (I), wherein R1 is optionally substituted alkyl, R2 is optionally substituted aryl or heteroaryl, A is cycloalkyloxy, cycloalkylalkoxy or alkoxy carrying one or more hydroxy moieties, the cycloalkyl moieties optionally further substituted by one or more methylene or lower alkyl groups, Q1, Q2 and Q3 each represents CH or CX or nitrogen, Z1 is oxygen or sulphur, Z2 is an NH or methylene and X is halogen and N-oxides thereof, and their esters, and prodrugs, pharmaceutically acceptable salts, and solvates (e.g. hydrates), thereof. Such compounds inhibit the production or physiological effects of TNF and inhibit cyclic AMP phosphodiesterase. The invention is also directed to pharmaceutical compositions containing compounds of formula (I), their pharmaceutical use and methods for their preparation.(FR) Cette invention porte sur des composés physiologiquement actifs de la formule (I) dans laquelle R1 est alkyle éventuellement substitué, R2 aryle ou hétéroaryle éventuellement substitués, A, cycloalkyloxy, cycloalkylalcoxy ou alcoxy porteurs d'un ou plusieurs fragments hydroxy, les fragments cycloalkyles pouvant éventuellement être, en outre, substitués par un ou plusieurs groupes méthylène ou alkyle inférieur, Q1, Q2 et Q3 représentent chacun CH, CX ou azote, Z1, l'oxygène ou soufre, Z2, NH ou méthylène et dans laquelle X représente halogène. L'invention concerne également leurs oxydes d'azote, leurs esters et précurseurs de médicaments, leurs sels acceptables du point de vue pharmaceutique ainsi que leurs solvates (des hydrates, par exemple). De tels composés, qui inhibent la production du facteur de nécrose tumorale ou ses effets physiologiques, inhibent également la phosphodiestérase de l'AMP cyclique. L'invention porte, de surcroît, sur des compositions pharmaceutiques contenant des composés de la formule I, sur leurs applications pharmaceutiques ainsi que sur des procédés d'élaboration de ces substances.