7-(2-甲酰基-5-氧代环戊基)庚酸甲酯 | 61659-10-7

• 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: 7-(2-甲酰基-5-氧代环戊基)庚酸甲酯
• 英文名称: 7-(2-formyl-5-oxo-cyclopentyl)-heptanoic acid methyl ester
• 英文别名: 5-formyl-2-oxo-cyclopentaneheptanoic acid methyl ester；2-(6-carboxyhexyl)cyclopentan-1-on-3-al methyl ester；Methyl 7-(2-formyl-5-oxocyclopentyl)heptanoate
• CAS: 61659-10-7
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: ZSXXSLGVUFUSGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  361.9±27.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(2-甲酰基-5-氧代环戊基)庚酸甲酯 在 sodium hydride 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 15-dehydroprostaglandin B₁ methyl ester
  参考文献：
  名称：

  Cupric bromide utilization in the synthesis of prostanoid intermediates

  摘要：

  DOI：

  10.1016/s0040-4039(00)81462-8
• 作为产物：
  描述：

  7-(2-氧代环戊基)庚酸甲酯 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 0.67h， 生成 7-(2-甲酰基-5-氧代环戊基)庚酸甲酯
  参考文献：
  名称：

  Cupric bromide utilization in the synthesis of prostanoid intermediates

  摘要：

  DOI：

  10.1016/s0040-4039(00)81462-8

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过程，特别是9,15-双氧代前列腺酸和前列腺-13-烯酸衍生物的过程，还包括相关的不饱和衍生物、同系物及其中间体。其中，将2-(ω-羧基-Y)环戊-2-烯-1-酮的低碳酸酯处理为亚硝甲烷，得到2-(ω-羧基-Y)-3-硝基甲基环戊-1-酮，然后将该化合物或其相应的1-羟基类似物转化为相应的醛，2-(ω-羧基-Y)环戊-1-酮-3-醛或1-羟基-2-(ω-羧基-Y)环戊-3-醛。将醛与由适当的威蒂格试剂制备的叶立得到的叶立体处理，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是1-6的整数，Alk是含有1-3个碳原子的烷基，产生对应的2-(ω-羧基-Y)-3-(3-氧代烷-1-烯基)环戊-1-酮或-1-醇，在这些化合物中，氧功能基可能通过常规手段选择性地保护和转化，不饱和键可能被还原为单键。前列腺酸衍生物具有类似前列腺素的生物活性。同时还公开了它们的使用方法。
• New prostaglandin-like diketals
  申请人：Merck Patent Gesellschaft mit beschrankter Haftung

  公开号：US04209444A1

  公开（公告）日：1980-06-24

  Compounds of formula ##STR1## their mirror images and racemic mixtures, and the physiologically acceptable salts thereof, wherein A and D each are ketalized carbonyl groups; B is --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 CH.sub.2 --, --CH(CH.sub.3)CH.sub.2 ----C(CH.sub.3).sub.2 CH.sub.2 -- or --CH.sub.2 O--; R.sup.1 is H or alkyl of 1-4 C-atoms; and R.sup.2 is alkyl of 3 to 5 C-atoms, phenyl or phenyl substituted one to three times by F, Cl, CF.sub.3, OH, OCH.sub.3, OC.sub.2 H.sub.5 or alkyl of 1 to 3 C-atoms inhibit aggregation and/or adhesion of thrombocytes.

  式子##STR1##及其镜像和外消旋混合物，以及其生理上可接受的盐，其中A和D分别为酮保护的羰基基团；B为--CH.sub.2 --，--CH(CH.sub.3)--，--C(CH.sub.3).sub.2 --，--CH.sub.2 CH.sub.2 --，--CH(CH.sub.3)CH.sub.2 ----C(CH.sub.3).sub.2 CH.sub.2 --或--CH.sub.2 O--；R.sup.1为H或1-4个C原子的烷基；R.sup.2为3至5个C原子的烷基，苯基或苯基被F，Cl，CF.sub.3，OH，OCH.sub.3，OC.sub.2 H.sub.5或1至3个C原子的烷基取代的苯基，能够抑制血小板的聚集和/或粘附。
• Methods
  申请人：Sattentau James Quentin

  公开号：US20070110759A1

  公开（公告）日：2007-05-17

  The presence of aldehydic groups on proteins and lipoproteins is associated with various pathological conditions such as atherosclerosis, diabetes and alcoholic liver disease. Respiratory syncytial virus (RSV) is a major cause of severe respiratory disease in infants and the elderly. RSV vaccine research has been impeded because a formalin-inactivated vaccine used in the 1960s predisposed infants to enhanced disease following subsequent natural infection. The molecular basis for the vaccine-induced hypersensitivity has not, however, been elucidated. We show here that addition of reactive carbonyl groups to ovalbumin (OVA) by treatment with glycolaldehyde or formaldehyde increases the protein's immunogenicity in mice, and biases the immune response towards a Th2-type response. The increased immunogenicity and the Th2-type response can both be abrogated by reductive elimination of the reactive carbonyl groups. We demonstrate that RSV inactivated by formaldehyde (FI-RSV), following a protocol used previously to prepare the vaccine, contains reactive carbonyl groups. Using a well-established model of FI-RSV vaccine-induced pathology, immunisation of mice with FI-RSV and subsequent challenge of the mice with live RSV induced Th2-type responses, lung eosinophilia and weight loss that were abrogated by reductive elimination of the reactive carbonyl groups. We thus propose that the addition of reactive carbonyl groups to RSV during inactivation is the major mechanism that drives the Th2-immune response and associated pathology. Moreover, we suggest that the addition of reactive carbonyl groups to other antigens, including vaccines, may be responsible for other hypersensitive and allergic reactions described in the literature.
• US4054741A
  申请人：——

  公开号：US4054741A

  公开（公告）日：1977-10-18
• US4073799A
  申请人：——

  公开号：US4073799A

  公开（公告）日：1978-02-14