3-oxo-oct-6-enoic acid methyl ester | 22617-63-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-oxo-oct-6-enoic acid methyl ester
• 英文别名: (Z)-methyl 3-oxo-6-octenoate；(Z)-methyl 3-oxooct-6-enoate；3-oxo-oct-6c-enoic acid methyl ester；3-Oxo-oct-6c-ensaeure-methylester；(Z)-3-oxo-6-octenoic acid methyl ester；cis-2-Oxo-5-hepten-1-carbonsaeure-methylester；methyl (Z)-3-oxooct-6-enoate
• CAS: 22617-63-6
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: KEFBZRDCTCSBIN-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3-oxo-oct-6-enoic acid methyl ester 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到(Z)-methyl 2-diazo-3-oxo-6-octenoate
  参考文献：
  名称：

  Enantioselective ring construction with control of side-chain stereochemistry. Synthesis of (+)-isoneonepetalactone

  摘要：

  DOI：

  10.1021/jo00248a016
• 作为产物：
  描述：

  (Z)-己-4-烯醛 在 磷酸酐 、 二甲基亚砜 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-oxo-oct-6-enoic acid methyl ester
  参考文献：
  名称：

  Enantioselective ring construction with control of side-chain stereochemistry. Synthesis of (+)-isoneonepetalactone

  摘要：

  DOI：

  10.1021/jo00248a016

文献信息

• Novel Synthesis of Highly Functionalized 14-β-Hydroxysteroids Related to Batrachotoxin and Ouabain
  作者：Stéphane Trudeau、Pierre Deslongchamps

  DOI：10.1021/jo0355606

  日期：2004.2.1

  The use of anionic polycyclization was investigated in an effort to develop a versatile and convergent synthesis of advanced tetracyclic intermediates of batrachotoxin and ouabain analogues. Two new 5-(trialkylsilyl)-2-cyclohexenones as A ring precursors and a new Nazarov intermediate (D ring precursor) were prepared for this purpose. The reaction of the unsaturated β-keto aldehyde A ring precursor

  研究了阴离子多环化的用途，目的是开发一种多功能和收敛的合成的梭状芽孢杆菌毒素和哇巴因类似物的高级四环中间体。为此，制备了两种新的作为A环前体的5-（三烷基甲硅烷基）-2-环己烯酮和一种新的Nazarov中间体（D环前体）。在随后的转化之后，不饱和β-酮醛A环前体与Nazarov中间体的烯醇盐的反应提供了完全控制立体化学的14-β-羟基类固醇。
• On the stereochemical course of cuprate-mediated homoconjugate addition to an activated cyclopropane
  作者：Douglass P. Taber、Kenneth H. Krewson、Krishna Raman、Arnold L. Rheingold

  DOI：10.1016/s0040-4039(01)81584-7

  日期：——

  Cuprate-mediated homoconjugate addition to activated cyclopropane 6 is shown to proceed with inversion of absolute configuration at the apical carbon of the cyclopropane.

  铜盐介导的均轭合物向活化的环丙烷6的添加显示出在环丙烷的顶碳处绝对构型的转化。
• Process for producing 3-formylcyclopentanone derivatives
  申请人：(Zaidanhojin) Sagami Chemical Research Center

  公开号：US04073799A1

  公开（公告）日：1978-02-14

  A novel process for producing 3-formylcyclopentanone derivatives which are useful intermediates for syntheses of five-membered ring compounds such as prostaglandins is disclosed. In the process, 3-formylcyclopentanone derivatives are produced starting from .beta.-dicarbonyl compounds and azides through several-step reactions.

  公开了一种用于生产3-甲酰基环戊酮衍生物的新工艺，这些衍生物是用于合成五元环化合物如前列腺素的中间体。在该工艺中，通过几步反应从β-二羰基化合物和叠氮化合物开始生产3-甲酰基环戊酮衍生物。
• Stereochemistry of the nucleophilic ring-opening of activated bicyclo-[3.1.0]Hexanes.
  作者：Daiei Tunemoto、Nobuhiko Araki、Kiyosi Kondo

  DOI：10.1016/s0040-4039(01)92563-8

  日期：1977.1
• Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (−)–Pironetin
  作者：Sara K. Coulup、David S. Huang、Henry L. Wong、Gunda I. Georg

  DOI：10.1021/acs.jmedchem.8b01774

  日期：2019.2.14

  Pironetin, the only crystallographically confirmed natural product to target a-tubulin, displays potent cytotoxic activity against sensitive and resistant A2780 ovarian cancer cell lines but is only marginally active in vivo. We now report that pironetin has a short half-life (<7 min) in human liver microsomes, suggesting that its limited in vivo efficacy is due to rapid metabolism. Further, we describe the discovery of epoxypironetin as pironetin's major metabolite in human liver microsomes.