(E)-3-acetylamino-2-methylbut-2-enoic acid ethyl ester | 852178-56-4

• 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: (E)-3-acetylamino-2-methylbut-2-enoic acid ethyl ester
• 英文别名: (2E)-ethyl 3-N-acetylamino-2-methyl-2-butenoate；(E)-ethyl 3-acetamido-2-methylbut-2-enoate；E-ethyl 3-acetamido-2-methyl-2-butenoate；ethyl (E)-3-acetamido-2-methylbut-2-enoate
• CAS: 852178-56-4
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: DIIGVOOFBVSWDN-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-acetylamino-2-methylbut-2-enoic acid ethyl ester 在 (R,R)-Me-BPE-Rh(I) 氢气 作用下， 以 苯 为溶剂， 20.0 ℃ 、620.52 kPa 条件下， 反应 72.0h， 生成 ethyl 3-N-acetylamino-2-methylbutanoate 、 ethyl 3-N-acetylamino-2-methylbutanoate
  参考文献：
  名称：

  An enantioselective synthesis of β2-amino acid derivatives

  摘要：

  Enantioselective hydrogenation of a series of (E)-alpha-substituted beta-amidoacrylates using Rh(I)-catalysts with chiral phosphine ligands (BPE, DuPHOS) gives beta(2)-amino acid derivatives with enantioselectivities of up to 67%. A beta(2,3)-amino acid derivative was also synthesised with similar enantioselectivity (<= 65%) from the corresponding prochiral enamide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.048
• 作为产物：
  描述：

  (Z)-3-acetylamino-2-methylbut-2-enoic acid ethyl ester 以 甲苯 为溶剂， 反应 7.0h， 以98%的产率得到(E)-3-acetylamino-2-methylbut-2-enoic acid ethyl ester
  参考文献：
  名称：

  An enantioselective synthesis of β2-amino acid derivatives

  摘要：

  Enantioselective hydrogenation of a series of (E)-alpha-substituted beta-amidoacrylates using Rh(I)-catalysts with chiral phosphine ligands (BPE, DuPHOS) gives beta(2)-amino acid derivatives with enantioselectivities of up to 67%. A beta(2,3)-amino acid derivative was also synthesised with similar enantioselectivity (<= 65%) from the corresponding prochiral enamide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.048

文献信息

• Pyrrole Synthesis via Allylic sp³ C−H Activation of Enamines Followed by Intermolecular Coupling with Unactivated Alkynes
  作者：Souvik Rakshit、Frederic W. Patureau、Frank Glorius

  DOI：10.1021/ja104305s

  日期：2010.7.21

  A conceptually novel pyrrole synthesis is reported, efficiently merging enamines and (unactivated) alkynes under oxidative conditions. In an intermolecular Rh catalyzed process, the challenging allylic sp(3) C-H activation of the enamine substrates is followed by the cyclization with the alkyne (R(3) = CO(2)R). Alternatively, in some cases (R(3) = CN), the enamine can be utilized for a vinylic sp(2)

  报道了一种概念上新颖的吡咯合成，可在氧化条件下有效地合并烯胺和（未活化的）炔烃。在分子间 Rh 催化过程中，烯胺底物的具有挑战性的烯丙基 sp(3) CH 活化之后是与炔烃 (R(3) = CO(2)R) 的环化。或者，在某些情况下 (R(3) = CN)，烯胺可用于乙烯基 sp(2) CH 活化。总共提供了 17 个产率高于 60% 的例子，以及初步机械研究的结果。
• Synthesis of α,β-unsaturated γ-amino esters with a quaternary center by ruthenium-catalyzed codimerization of N-acetyl α-arylenamines and acrylates
  作者：Qiu-Shi Wang、Jian-Hua Xie、Lu-Chuan Guo、Qi-Lin Zhou

  DOI：10.1039/c1ob06412f

  日期：——

  Ruthenium-catalyzed highly selective codimerization of N-acetyl α-arylenamines with ethyl acrylates is reported. This codimerization reaction provides a new efficient method for the synthesis of α,β-unsaturated γ-amino esters with a quaternary center.

  报道了一种铑催化的高选择性N-乙酰α-芳基胺与乙基丙烯酸酯的共聚合反应。该共聚合反应提供了一种合成具有四元中心的α,β-不饱和γ-氨基酯的新型高效方法。
• Method for the asymmetric hydrogenation of olefins utilising photoisomerisation
  申请人：DSM IP Assets B.V.

  公开号：EP2213638A1

  公开（公告）日：2010-08-04

  The present invention relates to a method for the preparation of a compound of formula (I), wherein R1 is different to R2; R3 is different to R4; and R1, R2, R3 and R4 are each a moiety other than hydrogen, which method comprises, i) photoirradiating at an intensity above ambient intensity a solution comprising a compound of formula (II), wherein R1, R2, R3 and R4 are as defined above, to form a solution of a mixture of compounds of formula (IIa) and (IIb), wherein R1, R2, R3and R4 are as defined above; and ii) contacting the mixture of compounds (IIa) and (IIb) with a hydrogen donating agent in the presence of an asymmetric hydrogenation catalyst, after initiation of i) and before termination of i).

  本发明涉及一种制备化合物(I)的方法，其中R1不同于R2；R3不同于R4；且R1、R2、R3和R4各自是除氢之外的基团，该方法包括，i) 在高于环境强度的光照强度下光照含有化合物(II)的溶液，其中R1、R2、R3和R4如上定义，以形成化合物(IIa)和(IIb)的混合物的溶液，其中R1、R2、R3和R4如上定义；和ii) 在i)启动后且i)终止前，将化合物(IIa)和(IIb)的混合物与氢捐体在不对称氢化催化剂存在下接触。
• Preparation of chiral cyclic amino acids and derivatives
  申请人：The Penn State Research Foundation

  公开号：US20040242889A1

  公开（公告）日：2004-12-02

  Cyclic &bgr;-(acylamino)acrylate derivatives were hydrogenated using Ru-chiral phosphine ligand catalysts and thereafter converted to the corresponding cyclic &bgr;-aminoacids in high yield and enantioselectivity according to the reaction scheme: 1

  使用Ru-手性膦配体催化剂对环状&bgr;-(酰胺基)丙烯酸酯衍生物进行氢化反应，然后根据反应方案将其转化为相应的环状&bgr;-氨基酸，收率和对映选择性均很高。1
• An Efficient Synthesis of 3-Substituted 3<i>H</i>-Pyrimidin-4-ones
  作者：Jae Uk Jeong、Xiaohong Chen、Attiq Rahman、Dennis S. Yamashita、Juan I. Luengo

  DOI：10.1021/ol049921v

  日期：2004.3.1

  [GRAPHICS]A novel and practical synthesis of 3-substituted 3H-pyrimidin-4-ones is described. The key step involves the cyclization of enamide esters, derived from readily available beta-keto esters, with trimethylaluminum and various primary amines.