4-cyclopropyl-2-oxo-3-butenoic acid ethyl ester | 95188-20-8

• 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: 4-cyclopropyl-2-oxo-3-butenoic acid ethyl ester
• 英文别名: ethyl 4-cyclopropyl-2-oxobut-3-enoate
• CAS: 95188-20-8
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: DWIHMENRPJUMAT-UHFFFAOYSA-N

物化性质

• 沸点：
  241.5±13.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-氧代-1,2,3,4-四氢萘-2-甲醛 、 4-cyclopropyl-2-oxo-3-butenoic acid ethyl ester 在 3-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-4-[[(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]amino]cyclobut-3-ene-1,2-dione 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Bifuctional Amino-Squaramides Catalyzed Asymmetric Spiroannulation Cascades with Aliphatic β,γ-Unsaturated α-Keto Esters: Controlling an Aldehyde Enolate

  摘要：

  A quinidine-derived squaramide Ib catalyzed cyclization reaction of beta-oxo aldehydes 1 and aliphatic or aromatic beta,gamma-unsaturated alpha-keto ester 2 is described. Using cyclic aldehyde substrates, this procedure provided a promising approach to a variety of spiro-3,4-dihydropyrans bearing three continuous quaternary and tertiary stereocenters in moderate to good yield with high stereoselectivities. Substituents on the nitrogen atoms of the squaramide moiety of the catalyst proved crucial to the reaction outcome. The stereochemistry of the three newly formed chiral centers (trans-selective) of the major product indicates a Micheal addition/hemiacetalization domino sequence for the present annulations.

  DOI：

  10.1021/jo202633c

文献信息

• Catalytic Three-Component Synthesis of Functionalized Naphtho[2,1-<i>b</i>]oxecines via a Double Bond Cleavage–Rearrangement Cascade
  作者：Cheng-Long Ji、Wen-Juan Hao、Jie Zhang、Fang-Zhou Geng、Ting Xu、Shu-Jiang Tu、Bo Jiang

  DOI：10.1021/acs.orglett.9b02367

  日期：2019.8.16

  A new double annulation cascade involving a [2 + 2] cycloaddition–retroelectrocyclization (CA–RE) process was first reported, leading to the generation of unprecedented dibenzoannulated naphtho[2,1-b]oxecines with good to excellent yields and high stereoselectivity through catalytic scission/recombination of C–C double bonds under the mild conditions. An Y(OTf)3-catalyzed three-component reaction of

  首次报道了涉及[2 + 2]环加成-逆电环化（CA-RE）过程的新双环带反应级联反应，从而产生了史无前例的二苯并环烷萘[ 2,1- b ]辛硫辛酮，具有良好的收率和优异的立体选择性，并通过在温和条件下催化双键断裂– C–C双键的重组。Y（OTf）3催化α-炔基萘-2-醇与β，γ-不饱和α-酮酸酯的三组分反应，可以使萘环直接扩环，并实现α-的碳-碳双键裂解/重排酮酸酯以提供大环结构。
• A tertiary amine catalyzed carbocyclization sequence to furnish spirocyclo hexene systems having vicinal quaternary stereocenters
  作者：Jindian Duan、Fangyi Cao、Xiaoqin Wang、Cheng Ma

  DOI：10.1039/c2cc37297e

  日期：——

  of enolates can be formed stepwise from enolisable 1,3-dicarbonyl-substituted propene systems in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) to accomplish a highly selective carbocyclization with beta,gamma-unsaturated alpha-keto esters, giving functionalized spiroketones with vicinal quaternary stereocenters.

  可以在催化量的1,4-二氮杂双环[2.2.2]辛烷（DABCO）存在下，由可烯丙基的1,3-二羰基取代的丙烯系统逐步形成两种类型的烯醇化物，从而实现具有β，γ的高选择性碳环化反应-不饱和的α-酮酸酯，可得到具有邻近四元立体中心的功能化螺酮。
• Bifuctional Amino-Squaramides Catalyzed Asymmetric Spiroannulation Cascades with Aliphatic β,γ-Unsaturated α-Keto Esters: Controlling an Aldehyde Enolate
  作者：Xiaoqin Wang、Weijun Yao、Zhihui Yao、Cheng Ma

  DOI：10.1021/jo202633c

  日期：2012.3.16

  A quinidine-derived squaramide Ib catalyzed cyclization reaction of beta-oxo aldehydes 1 and aliphatic or aromatic beta,gamma-unsaturated alpha-keto ester 2 is described. Using cyclic aldehyde substrates, this procedure provided a promising approach to a variety of spiro-3,4-dihydropyrans bearing three continuous quaternary and tertiary stereocenters in moderate to good yield with high stereoselectivities. Substituents on the nitrogen atoms of the squaramide moiety of the catalyst proved crucial to the reaction outcome. The stereochemistry of the three newly formed chiral centers (trans-selective) of the major product indicates a Micheal addition/hemiacetalization domino sequence for the present annulations.