methyl (9E)-11-oxoundec-9-enoate | 63024-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (9E)-11-oxoundec-9-enoate
• 英文别名: methyl (E)-11-oxoundec-9-enoate；methyl 11-oxo (E) 9-undecenoate；11-Oxo-(E)-undec-9-ensaeuremethylester；11-Oxoundec-(E)-9-en-saeuremethylester；Methyl (9E)-11-oxo-9-undecenoate
• CAS: 63024-88-4
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: MGEJSRKZEJDCJG-VQHVLOKHSA-N

物化性质

• 保留指数：
  1698

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• 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

• 作为反应物：
  描述：

  methyl (9E)-11-oxoundec-9-enoate 在 lithium aluminium tetrahydride 作用下， 生成 (E10,Z12)-hexadeca-10,12-dien-1-ol
  参考文献：
  名称：

  信息素XI烯醛的古佛莱德（E），（Z）-二烯。塞纳衍生物和同源物。

  摘要：

  DOI：

  10.1016/s0040-4039(01)92566-3
• 作为产物：
  描述：

  10-烯酸甲酯 生成 methyl (9E)-11-oxoundec-9-enoate
  参考文献：
  名称：

  A versatile synthon from castor oil: a direct, practical and novel route to 9,11-etheno-PGH

  摘要：

  DOI：

  10.1016/s0040-4039(01)94688-x

文献信息

• Synthesis of Six Epoxyketooctadecenoic Acid (EKODE) Isomers, Their Generation from Nonenzymatic Oxidation of Linoleic Acid, and Their Reactivity with Imidazole Nucleophiles
  作者：De Lin、Jianye Zhang、Lawrence M. Sayre

  DOI：10.1021/jo701373f

  日期：2007.12.1

  of six EKODE regio- and stereoisomers, two trans α‘,β‘-epoxy-α,β-enones, and two trans and the two cis γ,δ,-epoxy-α,β-enones was accomplished, with the key steps being Wittig-type reactions and aldol condensations. All six EKODE isomers were confirmed by HPLC to be generated in the autoxidation of linoleic acid promoted by Fe(II)/ascorbic acid through spiking in of authentic samples. On the basis of

  作为亚油酸氧化产物的一类，在体内和体外形成环氧酮十八碳烯酸（EKODEs）通过由酶促途径或非酶促途径引发的自由基机制。迄今为止，它们是由亚油酸衍生的氢过氧化物的还原分解而以小规模的形式通常以异构体混合物的形式获得的。这些化合物由于其强大的生物活性和共价修饰蛋白质的能力而引起了人们的极大兴趣。完成了六个EKODE区域和立体异构体，两个反式α'，β'-环氧-α，β-烯酮的合成，以及两个反式和两个顺式γ，δ，-环氧-α，β-烯酮的合成。关键步骤是维蒂希型反应和羟醛缩合。HPLC证实所有六种EKODE异构体都是通过掺入真实样品而在Fe（II）/抗坏血酸促进的亚油酸自氧化中生成的。Ñ α -benzoyl-升组氨酸与autoxidizing亚油酸和与各个EKODE异构体相比，因为是与咪唑的亲核试剂的各种EKODE反应的动力学。通过咪唑与通用EKODE-（E）-I类似物反应的NMR研究，证实了His-
• The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands
  作者：Mazhar Iqbal、Patricia Duffy、Paul Evans、George Cloughley、Bernard Allan、Agustí Lledó、Xavier Verdaguer、Antoni Riera

  DOI：10.1039/b814619e

  日期：——

  5-Alkylidenecyclopent-2-enones 15a–q may be prepared via a conjugate addition–Peterson olefination sequence, best achieved in one-pot, using exo-2-trimethylsilyl-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-one 12, followed by a retro-Diels–Alder reaction. The geometry of the exocyclic alkene may be controlled according to the use of organometallic species in the conjugate addition step; organocuprate reagents are found to selectively lead to the formation of E-exocyclic alkene adducts, whereas Grignard reagents favour the formation of Z-alkenyl isomers. The use of enantiomerically enriched 12, accessed from an asymmetric Pauson–Khand reaction, affords the corresponding enantioenriched 5-alkylidenecyclopent-2-enones and this approach is exemplified by the short, stereoselective total syntheses of two cyclopentenone phytoprostanes 51 and 13,14-dehydrophytoprostane J165. The ability of this family of synthetic compounds to activate the peroxisome proliferator activated receptor-γ is reported.

  5-烷叉环戊-2-烯酮15a–q可通过共轭加成-Peterson烯化序列制备，最佳方法为在一锅中使用外型2-三甲基硅基-3a,4,7,7a-四氢-4,7-亚甲基茚-1-酮12，接着进行逆Diels-Alder反应。根据共轭加成步骤中使用的有机金属物种，可以控制外部烯烃的几何形状：有机铜酸盐试剂发现选择性地导致E-外烯烃加合物的形成，而Grignard试剂有利于Z-烯基异构体的形成。使用手性富集的12（通过不对称Pauson-Khand反应获得），得到相应的手性富集的5-烷叉环戊-2-烯酮，这种方法通过两个环戊烯酮植物激素51和13,14-脱氢植物激素J165的简短、立体选择性全合成得到了例证。报道了这一系列合成化合物活化过氧化物酶体增殖物激活受体-γ的能力。
• METHODS OF MAKING ORGANIC COMPOUNDS BY METATHESIS
  申请人：Elevance Renewable Sciences, Inc.

  公开号：EP3281931A1

  公开（公告）日：2018-02-14

  Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

  本发明描述了通过偏合成化学制造有机化合物的方法。本发明的方法特别适用于从可再生原料（如天然油）中提取的起始组合物开始制造工业上重要的有机化合物。这些方法利用与烯烃化合物的交叉甲基化步骤，生成具有预定双键位置的官能化烯中间体。一旦分离出来，官能化烯中间体可进行自甲基化或交叉甲基化（例如与第二种官能化烯），以生产所需的有机化合物或其前体。该方法可用于制造双官能团有机化合物，如二酸、二酯、二羧酸盐、酸/酯、酸/胺、酸/醇、酸/醛、酸/酮、酸/卤化物、酸/腈、酯/胺、酯/醇、酯/醛、酯/酮、酯/卤化物、酯/腈等。
• Methods of making organic compounds by metathesis
  申请人：Wilmar Trading Pte Ltd

  公开号：US10906861B2

  公开（公告）日：2021-02-02

  Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

  本发明描述了通过偏合成化学制造有机化合物的方法。本发明的方法特别适用于从可再生原料（如天然油）中提取的起始组合物开始制造工业上重要的有机化合物。这些方法利用与烯烃化合物的交叉甲基化步骤，生成具有预定双键位置的官能化烯中间体。一旦分离出来，官能化烯中间体可进行自甲基化或交叉甲基化（例如与第二种官能化烯），以生产所需的有机化合物或其前体。该方法可用于制造双官能团有机化合物，如二酸、二酯、二羧酸盐、酸/酯、酸/胺、酸/醇、酸/醛、酸/酮、酸/卤化物、酸/腈、酯/胺、酯/醇、酯/醛、酯/酮、酯/卤化物、酯/腈等。
• Crilley, Martine M. L.; Golding, Bernard T.; Pierpoint, Colin, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2061 - 2068
  作者：Crilley, Martine M. L.、Golding, Bernard T.、Pierpoint, Colin

  DOI：——

  日期：——