methyl 3-oxonon-8-ene-1-carboxylate | 128738-23-8

• 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: methyl 3-oxonon-8-ene-1-carboxylate
• 英文别名: methyl 3-oxonona-8-enoate；3-oxo-non-8-enoic acid methyl ester；3-Oxo-non-8-ensaeure-methylester；Methyl 3-oxonon-8-enoate
• CAS: 128738-23-8
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: LWVXRCJEYCQYJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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 3-oxonon-8-ene-1-carboxylate 在 palladium on activated charcoal 、 Grubbs catalyst first generation 1,3,4-trimethylimidazolidin-2-one 、 氢气 、 四丁基碘化铵 、 potassium carbonate 、 lithium chloride 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 (R)-3-methyl-1,12-dioxocyclopentadecane
  参考文献：
  名称：

  闭环复分解在（R）-（+）-muscopyridine的首次全合成中的应用：绝对立体化学的测定

  摘要：

  DOI：

  10.1021/jo000785r
• 作为产物：
  描述：

  6-heptenoyl chloride 、 乙酰乙酸乙酯钠 在 乙醚 作用下， 生成 methyl 3-oxonon-8-ene-1-carboxylate
  参考文献：
  名称：

  157.合成除虫菊酯的实验。第八部分 茉莉酮的立体化学和二氢吡喃酮的身份

  摘要：

  DOI：

  10.1039/jr9520000869

文献信息

• Novel Intramolecular Cyclopropanation Reaction of Unsaturated β-Keto Esters
  作者：Dan Yang、Qiang Gao、Chi-Sing Lee、Kung-Kai Cheung

  DOI：10.1021/ol0265158

  日期：2002.9.1

  esters are versatile intermediates for the synthesis of many biologically active natural products. Here we report a new intramolecular cyclopropanation reaction of unsaturated beta-keto esters. In the presence of I(2), Et(3)N, and Lewis acids such as Mg(ClO(4))(2) and Yb(OTf)(3), beta-keto esters 1 bearing various olefin substituents were transformed to fused cyclopropanes 2 in a highly stereospecific manner

  [反应：见正文]熔融的环丙烷β-酮酸酯是用于合成许多具有生物活性的天然产物的通用中间体。在这里，我们报告不饱和的β-酮酯的新的分子内环丙烷化反应。在I（2），Et（3）N和Lewis酸（例如Mg（ClO（4））（2）和Yb（OTf）（3））的存在下，对带有各种烯烃取代基的β-酮酯1进行了转化以高度立体定向的方式，以中等至良好的产率合成稠合的环丙烷2。还研究了反应机理。
• Lanthanide Triflate-Promoted Palladium-Catalyzed Cyclization of Alkenyl β-Keto Esters and Amides
  作者：Dan Yang、Jin-Heng Li、Qiang Gao、Yi-Long Yan

  DOI：10.1021/ol0349110

  日期：2003.8.1

  graphicsLanthanide triflates were found to promote the palladium-catalyzed cyclization of alkenyl beta-keto esters and amides. In the presence of catalytic amounts of PdCl2(MeCN)(2) and Ln(OTf)(3), various alkenyl beta-keto esters and amides underwent regioselective cyclization reactions to give six-, seven-, or eight-membered-ring carbocycles in moderate to excellent yields.
• Generation and Cycloaddition Behavior of Spirocyclic Carbonyl Ylides. Application to the Synthesis of the Pterosin Family of Sesquiterpenes
  作者：Albert Padwa、Erin A. Curtis、Vincent P. Sandanayaka

  DOI：10.1021/jo951371e

  日期：1996.1.1

  The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)cyclopropane and ethyl 3-(1-acetyl-cyclopropyl)-2-diazo-3-oxopropiolate with various dipolarophiles afforded dipolar cycloadducts in good yield. The reaction involves the formation of a rhodium carbenoid and subsequent transannular cyclization of the electrophilic carbon onto the adjacent keto group to generate a five-membered cyclic carbonyl ylide which undergoes a subsequent dipolar cycloaddition reaction. The regiochemical results encountered can be rationalized on the basis of FMO considerations. For carbonyl ylides, the HOMO dipole is dominant for reactions with electron deficient dipolarophiles, while the LUMO becomes important for cycloaddition to more electron rich species. A short synthesis of several members of the pterosin family of sesquiterpenes is described in which the key step involves a dipolar cycloaddition using a carbonyl ylide. The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)-cyclopropane with cyclopentenone afforded a dipolar cycloadduct in good yield as a 4:1 mixture of diastereomers. Treatment of the major cycloadduct with triphenylphosphonium bromide in the presence of sodium hydride gave the expected Wittig product. The reaction of this compound with acid in the presence of various solvents gave rise to several members of the pterosin family. The overall sequence of reactions can best be described as proceeding by an initial oxy-bridge ring opening followed by dehydration and a subsequent acid-catalyzed cyclopropyl ring opening. The facility of the process is undoubtedly related to the aromaticity gained in the final step.
• Iqbal, Javed; Pandey, Anu, Synthetic Communications, 1990, vol. 20, # 5, p. 665 - 670
  作者：Iqbal, Javed、Pandey, Anu

  DOI：——

  日期：——
• IGBAL, JAVED;PANDEY, ANU, SYNTH. COMMUN., 20,(1990) N, C. 665-670
  作者：IGBAL, JAVED、PANDEY, ANU

  DOI：——

  日期：——