ethyl 3-nonenoate | 91213-30-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-nonenoate
• 英文别名: 3-nonenoic acid ethyl ester；ethyl non-3-enoate
• CAS: 91213-30-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: KQCNXVHFHZAHDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-nonenoate 、 间氯过氧苯甲酸 在 氢氧化钙 、 Calcium o-chlorobenzoate 、 二氯甲烷 、 Sodium sulfate-III 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 以24.6 g of crude 3,4-epoxynonanoic acid ethyl ester were obtained (93% pure according to GC)的产率得到3,4-Epoxynonanoic acid ethyl ester
  参考文献：
  名称：

  Novel Use of Nonenolide

  摘要：

  本发明涉及使用非烯酮来赋予、改变和/或增强一种或多种气味或口味印象，所述气味或口味印象来自于草、香豆素、内酯和口感丰富度的组合。

  公开号：

  US20070297993A1
• 作为产物：
  描述：

  乙醇 、 1-辛烯-3-醇乙酸酯 、 一氧化碳 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex N,N-二异丙基乙胺 、 三苯基膦 、 sodium bromide 作用下， 50.0 ℃ 、3.04 MPa 条件下， 反应 20.0h， 以83%的产率得到ethyl 3-nonenoate
  参考文献：
  名称：

  Palladium(0)-catalyzed alkoxycarbonylation of allyl phosphates and acetates

  摘要：

  Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50-degrees-C proceeds highly efficiently to give the corresponding beta,gamma-unsaturated esters. The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50-degrees-C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively. The carbonylation takes place at the least substituted allylic positions with inversion of configuration. Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl 2-cyclohexene-1,5-dicarboxylate (trans-17) selectively. Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give pi-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.

  DOI：

  10.1021/jo00058a040

文献信息

• A Convenient Synthesis of β,γ-Unsaturated Carboxylic Acid Derivatives via Carbonylation of (η³-Allyl)Fe(CO₂NO Complexes
  作者：Saburo Nakanishi、Takeshi Yamamoto、Naoyuki Furukawa、Yoshio Otsuji

  DOI：10.1055/s-1994-25533

  日期：——

  One-pot reaction of allyl halides with [Bu4N]+[Fe(CO)3(NO)]- followed by treatment with 1,2-bis(diphenylphosphino)ethane gave βγ-unsaturated acyl iron complexes in good yields via regioselective carbonylation with retention of configuration of the allylic double bond. β,γ-Unsaturated carboxylic acid esters and amides were prepared upon treatment of the acyl iron complexes with alcohols and amines in the presence of iodine.

  一步反应法将烯丙基卤与[Bu4N]+[Fe(CO)3(NO)]-反应，随后用1,2-双(二苯膺)乙烷处理，通过区域选择性羰基化并保持烯丙基双键构型，以良好产率得到βγ-不饱和酰基铁配合物。在碘的存在下，将这些酰基铁配合物与醇和胺反应，制备了β,γ-不饱和羧酸酯和酰胺。

表征谱图