ethyl 2-propylpenta-2,3-dienoate

• 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 2-propylpenta-2,3-dienoate
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: CMQPNSJCCJAPDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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 2-propylpenta-2,3-dienoate 在 copper(ll) bromide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以84%的产率得到4-Bromo-5-methyl-3-propyl-5H-furan-2-one
  参考文献：
  名称：

  CuBr2-mediated direct aqueous bromolactonization of 2,3-allenoates. An efficient access to β-bromobutenolides

  摘要：

  An efficient procedure for the synthesis of beta -bromobutenolides was developed. 2,3-Allenoates with different substitution patterns react with CuBr2 in aqueous ethanol at 80-85 degreesC to afford the corresponding beta -bromobutenolides in moderate to excellent yields (up to 97%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00634-7
• 作为产物：
  描述：

  丙酰氯 、 [1-(ethoxycarbonyl)butyl]triphenylphosphonium bromide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到ethyl 2-propylpenta-2,3-dienoate
  参考文献：
  名称：

  A Convenient Allenoate-Based Synthesis of 2-Quinolin-2-yl Malonates and β-Ketoesters

  摘要：

  N-protected o-aminobenzaldehydes smoothly react with alpha,gamma- dialkylallenoates under Bronsted basic conditions to yield 2,3-disubstituted quinolines. This three step reaction cascade of Michael addition, aldol condensation, adn 1,3 N -> C rearrangement uses the complete protecting group as a building block in a highly efficient C,C-bond formation of a new all carbon quaternary center. Carbamate protected substrates (N-Boc, N-Cbz, N-Alloc) thus give 2-quinolin-2-yl-malonates, while amide protected substres (NAc,NBz) afford 2 quinolin 2-yl-beta-ketoesters in high yields.

  DOI：

  10.1021/ol502554e

文献信息

• Regio- and Stereoselective Alkenylation of Allenoates with <i>gem</i>-Difluoroalkenes: Facile Access to Fluorinated 1,4-Enynes Bearing an All-Carbon Quaternary Center
  作者：Qi-Qi Zhang、Shi-Yong Chen、E Lin、Honggen Wang、Qingjiang Li

  DOI：10.1021/acs.orglett.9b00775

  日期：2019.5.3

  A regio- and stereoselective synthesis of fluorinated 1,4-enynes bearing an all-carbon quaternary center at the propargylic position is developed. The synthesis starts from readily available allenoates and gem-difluoroalkenes and proceeds via a key alkynylenolate intermediate following a nucleophilic addition/β-F elimination. This reaction occurs under mild reaction conditions with good tolerance to

  开发了在炔丙基位置带有全碳四元中心的氟化1,4-烯炔的区域和立体选择性合成。从容易获得的联烯酸酯和合成启动宝石-difluoroalkenes并且进行经由键alkynylenolate中间以下的亲核加成/β-F的消除。该反应在对各种官能团具有良好耐受性的温和反应条件下发生。产品的进一步转化证明了合成的效用。此外，该反应还可以通过使用3，3-二取代的脲基酸酯而应用于α-烯基脲基酸酯的合成。
• Manganese(I)‐Catalyzed Regio‐ and Stereoselective 1,2‐Diheteroarylation of Allenes: Combination of C−H Activation and Smiles Rearrangement
  作者：Shi‐Yong Chen、Xiang‐Lei Han、Jia‐Qiang Wu、Qingjiang Li、Yunyun Chen、Honggen Wang

  DOI：10.1002/anie.201704952

  日期：2017.8.7

  functional molecules. A MnI-catalyzed 1,2-diheteroarylation of allenes via a C−H activation/Smiles rearrangement cascade is presented. The reaction occurred under additive-free or even solvent-free conditions, which allowed the creation of two C−C and one C−N bonds in a single operation. A series of structurally diverse bicyclic or tricyclic compounds bearing an exocyclic double bond were constructed in

  杂芳烃是功能分子中重要的结构基序。提出了一个Mn I通过CH-H / Smiles重排级联反应催化的1，2-二烯丙基异戊烯基化反应。该反应在无添加剂甚至无溶剂的条件下发生，这允许在一次操作中生成两个C C和一个C N键。一系列结构良好的具有环外双键的双环或三环化合物以优异的效率构建。产物的脱羧开环导致邻位双杂芳基的容易合成。演示了合成应用，并进行了初步的力学研究。
• 10.1021/acs.orglett.4c01730
  作者：Shi, Yaqi、Fu, Chunling、Zheng, Jian、Ma, Shengming

  DOI：10.1021/acs.orglett.4c01730

  日期：——

  Photoinduced cyclization of 2,3-allenoic acids with sulfonyl chloride providing an efficient synthesis of 4-sulfonylated furan-2(5H)-ones under mild reaction conditions has been achieved. The reaction enjoys a high chemoselectivity and tolerates a wide range of functional groups. The catalytic cycle has been validated through control experiments, cyclic voltammetry studies, and Stern–Volmer quenching

  已经实现了 2,3-联烯酸与磺酰氯的光诱导环化，从而在温和的反应条件下有效合成了 4-磺酰化呋喃-2(5 H )-酮。该反应具有较高的化学选择性并能耐受多种官能团。催化循环已通过对照实验、循环伏安研究和 Stern-Volmer 猝灭研究得到验证。
• Guanidine-Catalyzed γ-Selective Morita–Baylis–Hillman Reactions on α,γ-Dialkyl-Allenoates: Access to Densely Substituted Heterocycles
  作者：Philipp Selig、Aleksej Turočkin、William Raven

  DOI：10.1055/s-0033-1339471

  日期：——

  N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) was discovered as an excellent catalyst for the Morita-Baylis-Hillman reaction for previously hard-to-activate ,-dialkyl allenoate substrates. The obtained densely substituted allenic alcohols, which are generally inaccessible with other Lewis base catalysts, could be further converted into 2,5-dihydrofuran and 2H-pyran-2-one heterocyclic structures with challenging substitution patterns.
• A Convenient Allenoate-Based Synthesis of 2-Quinolin-2-yl Malonates and β-Ketoesters
  作者：Philipp Selig、William Raven

  DOI：10.1021/ol502554e

  日期：2014.10.3

  N-protected o-aminobenzaldehydes smoothly react with alpha,gamma- dialkylallenoates under Bronsted basic conditions to yield 2,3-disubstituted quinolines. This three step reaction cascade of Michael addition, aldol condensation, adn 1,3 N -> C rearrangement uses the complete protecting group as a building block in a highly efficient C,C-bond formation of a new all carbon quaternary center. Carbamate protected substrates (N-Boc, N-Cbz, N-Alloc) thus give 2-quinolin-2-yl-malonates, while amide protected substres (NAc,NBz) afford 2 quinolin 2-yl-beta-ketoesters in high yields.