6-(5-氧代环戊烯-1-基)己酸甲酯 | 40649-46-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 6-(5-氧代环戊烯-1-基)己酸甲酯
• 英文名称: 2<6-(carbomethoxy)hexyl>-2-cyclopentenone
• 英文别名: 6-(5-oxo-1-cyclopentenyl)hexansaeure-methylester；Methyl-ω-(2-oxo-5-cyclopentenyl)-capronat；2-(5-Methoxycarbonylpentyl)-2-cyclopenten-1-on；Methyl 6-(5-oxo-1-cyclopenten-1-yl)hexanoate；methyl 6-(5-oxocyclopenten-1-yl)hexanoate
• CAS: 40649-46-5
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: QSDUSNPSRJVAGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  11,11-dimethoxy-8-oxoundecansaeure-methylester 在 sodium methylate 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 生成 6-(5-氧代环戊烯-1-基)己酸甲酯
  参考文献：
  名称：

  合成vonω-（5-Oxo-1-cyclopentenyl）alkansäure-methylesternaus 2-Nitrocycloalkanonen

  摘要：

  从2-硝基环烷酮开始合成ω-（5-Oxo-1-环戊烯基）链烷酸甲酯

  DOI：

  10.1002/hlca.19870700207

文献信息

• Derivatives of prostanoic acid
  申请人：Ayerst McKenna & Harrison Ltd.

  公开号：US04054741A1

  公开（公告）日：1977-10-18

  Process for preparing prostanoic acid derivatives, in particular derivatives of 9,15-dioxygenated prostanoic acid and prost-13-enoic acid, related additionally unsaturated derivatives, homologs thereof and intermediates therefor, in which a lower alkyl ester of 2-(.omega.-carboxy-Y)cyclopent-2-en-1-one in which Y is CH.sub.2 --(a)--(CH.sub.2).sub.m wherein (a) is CH.sub.2 CH.sub.2, CH.dbd.CH or C.tbd.C and m is an integer from 2 - 4 is treated with nitromethane to yield 2-(.omega.-carboxy-Y)-3-nitromethyl-cyclopentan-1-one and the latter compound or its corresponding 1-hydroxy analog are converted to the corresponding aldehyde, 2-(.omega.-carboxy-Y)cyclopentan-1-on-3-al or 1-hydroxy-2-(.omega.-carboxy-Y)cyclopentan-3-al, respectively. Treatment of the aldehyde with the ylid prepared from the appropriate Wittig reagent, preferably a dimethyl 2-oxoalkylphosphonate of the formula (AlkO).sub.2 P(O)CH.sub.2 CO(CH.sub.2).sub.n CH.sub.3 in which n is an integer of from 1-6 and Alk is an alkyl containing from 1 - 3 carbon atoms yields the corresponding derivatives of 2-(.omega.-carboxy-Y)-3-(3-oxoalk-1-enyl)cyclopentan-1-one or -1-o1 in which the oxygen functions may be selectively protected and transformed by conventional means, and in which the unsaturated bonds may be reduced to a single bond. The prostanoic acid derivatives possess prostaglandin like biological activities. Methods for their use are also disclosed.

  制备前列腺酸衍生物的方法，特别是9,15-二氧化前列腺酸和前列腺-13-烯酸衍生物，以及相关的不饱和衍生物，同系物和其中间体。其中，将2-（ω-羧基-Y）环戊-2-烯-1-酮的较低烷基酯处理成2-（ω-羧基-Y）-3-硝基甲基环戊烷-1-酮，然后将后者化合成相应的醛，即2-（ω-羧基-Y）环戊烷-1-酮-3-醛或1-羟基-2-（ω-羧基-Y）环戊烷-3-醛。将醛与适当的Wittig试剂制备的ylid处理，最好是公式（AlkO）2P（O）CH2CO（CH2）nCH3的二甲基2-氧代烷基膦酸酯，其中n为1-6的整数，Alk为含1-3个碳原子的烷基，得到相应的2-（ω-羧基-Y）-3-（3-氧代烷基-1-烯基）环戊烷-1-酮或-1-o1衍生物，其中氧功能基可以通过常规手段选择性地保护和转化，不饱和键可以还原为单键。前列腺酸衍生物具有类前列腺素的生物活性。还公开了它们的使用方法。
• Cardinale, G.; Laan, J. A. M.; Russel, S. W., Recueil des Travaux Chimiques des Pays-Bas, 1982, vol. 101, # 6, p. 199 - 202
  作者：Cardinale, G.、Laan, J. A. M.、Russel, S. W.、Ward, J. P.

  DOI：——

  日期：——
• PROSTAGLANDIN DERIVATIVES, PROCESSES FOR PREPARING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAID DERIVATIVES
  申请人：IBI- Istituto Biochimico Italiano Giovanni Lorenzini S.p.A.

  公开号：EP0319576B1

  公开（公告）日：1992-01-08
• PROSTAGLANDINDERIVATE, VERFAHREN UND PHARMAZEUTISCHE ZUSAMMENSETZUNGEN
  申请人：IBI- Istituto Biochimico Italiano Giovanni Lorenzini S.p.A.

  公开号：EP0319576A1

  公开（公告）日：1989-06-14
• US4054741A
  申请人：——

  公开号：US4054741A

  公开（公告）日：1977-10-18