ethyl 3-acetamido-3-phenylpropanoate | 7554-23-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-acetamido-3-phenylpropanoate
• 英文别名: 3-acetylamino-3-phenyl-propionic acid ethyl ester；3-Acetylamino-3-phenyl-propionsaeure-aethylester；(+/-)-3-Acetamino-3-phenyl-propionsaeure-aethylester
• CAS: 7554-23-6
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: UZZYTARXVXBRHD-UHFFFAOYSA-N

物化性质

• 沸点：
  416.3±38.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  ethyl 3-acetamido-3-phenylpropanoate 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以95%的产率得到ethyl 3-phenyl-3-[(1-thioxoethyl)amino]propanoate
  参考文献：
  名称：

  Thionation ofω-Acylamino Ketones withLawesson's Reagent: Convenient Synthesis of 1,3-Thiazoles and 4H-1,3-Thiazines

  摘要：

  The reaction of omega -acylamino ketones with Lawesson's reagent (=2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide; LR) is described. Treatment of 2-acylamino ketones 1 (n = 0) with LR gave 1,3-thiazole derivatives 3 in good yields (Scheme I and Table 1). The 4H-1,3-thiazines 4 were obtained as main products by treatment of 3-acylamino ketones 2 (n = 1) with an equimolar amount of LR, while mainly the corresponding 3-(thioacyl)amino ketones 5 were isolated when 0.5 equiv. of LR was used. The 3-acylamino esters 7 also reacted with LR to give the corresponding 3-(thioacyl)amino esters 8 (Scheme 3 and Table 2).

  DOI：

  10.1002/1522-2675(20010815)84:8<2347::aid-hlca2347>3.0.co;2-n
• 作为产物：
  描述：

  3-苯基环氧乙烷甲酸乙酯 在 N,N-二甲基乙醇胺 、 sodium azide 、 samarium diiodide 、 氯化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 28.75h， 生成 ethyl 3-acetamido-3-phenylpropanoate
  参考文献：
  名称：

  Reduction of 2-Acylaziridines by Samarium(II) Iodide. An Efficient and Regioselective Route to β-Amino Carbonyl Compounds.

  摘要：

  DOI：

  10.1016/s0040-4020(97)00576-0

文献信息

• C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin
  申请人：Bao Jian

  公开号：US20050228190A1

  公开（公告）日：2005-10-13

  Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C 1 -symmetric bisphosphine ligands bound to transition metals.

  通过对原生手性烯烃进行对映选择性加氢制备(S)-(+)-3-(氨甲基)-5-甲基己酸及其结构相关化合物的材料和方法已被披露。这些方法采用了新颖的手性催化剂，其中包括与过渡金属结合的C1对称双膦配体。
• Oxidative nucleophilic substitution: transformation of alkylboronic derivatives
  作者：Clément Cazorla、Estelle Métay、Marc Lemaire

  DOI：10.1016/j.tet.2011.09.055

  日期：2011.11

  An efficient amidation reaction is described in this paper. Potassium alkyltrifluoroborate salts can be transforming to amides from nitriles in the presence of copper acetate and boron trifluoride. An extension of this reaction allowed the formation of amines, ethers, and C–C bond.

  本文描述了一种有效的酰胺化反应。在乙酸铜和三氟化硼的存在下，烷基三氟硼酸钾盐可从腈转化为酰胺。反应的延伸允许形成胺，醚和CC键。
• NOVEL BISPHOSPHINE LIGAND
  申请人：WATANABE Michimasa

  公开号：US20080242534A1

  公开（公告）日：2008-10-02

  A compound represented by the following general formula (I): [wherein R 1 represents hydrogen atom, or an alkyl group, R 2 represents a hydroxyalkyl group, or a triarylmethyloxyalkyl group, or R 1 and R 2 combine together to represent —C(R 3 )(R 4 )— (R 3 and R 4 represent hydrogen atom, an alkyl group, or hydroxyl group, or R 3 and R 4 may combine together to represent oxo group), or —C(R 5 )(R 6 )—O—C(R 7 )(R 8 )— (R 5 to R 8 represent hydrogen atom, an alkyl group, or hydroxyl group, or R 5 and R 6 may combine together to represent oxo group, and R 7 and R 8 may combine together to represent oxo group); Ar 1 to Ar 4 independently represent an aryl group (the aryl group may have 1 to 5 of the same or different substituents), *1 to *4 indicate asymmetric carbons, and configurations are cis between *1 and *2, cis between *3 and *4, and trans between *2 and *3]. An optically active phosphine ligand which can be easily synthesized and gives a transition metal complex showing superior asymmetric catalyst activity is provided.

  提供了一个由以下一般式（I）表示的化合物：【其中R1代表氢原子，或烷基团，R2代表羟基烷基团，或三芳基甲氧基烷基团，或R1和R2结合在一起表示—C(R3)(R4)—（R3和R4代表氢原子，烷基团，或羟基，或R3和R4可以结合在一起表示酮基），或—C(R5)(R6)—O—C(R7)(R8)—（R5到R8代表氢原子，烷基团，或羟基，或R5和R6可以结合在一起表示酮基，R7和R8可以结合在一起表示酮基）；Ar1到Ar4独立地代表芳基（芳基可能具有1到5个相同或不同的取代基），*1到*4表示不对称碳，配置在*1和*2之间为顺式，*3和*4之间为顺式，*2和*3之间为反式】。提供了一种可以轻松合成并给出显示出优越不对称催化剂活性的过渡金属配合物的光学活性膦配体。
• Iridium‐Catalyzed Hydrogenation of β‐Dehydroamino Acid Derivatives Using Monodentate Phosphoramidites
  作者：Stephan Enthaler、Giulia Erre、Kathrin Junge、Kristin Schröder、Daniele Addis、Dirk Michalik、Marko Hapke、Dmitry Redkin、Matthias Beller

  DOI：10.1002/ejoc.200800241

  日期：2008.7

  asymmetric hydrogenation of 13 different β-dehydroamino acid derivatives to give optically active β-amino acid esters has been examined. Readily accessible monodentate octahydrobinaphthol-based phosphoramidites were used as chiral ligands. Good to excellent enantioselectivities and yields were obtained for the E isomers, whereas poorer catalyst performance was found for the Z isomers. Importantly, to obtain

  已经研究了铱催化的 13 种不同的 β-脱氢氨基酸衍生物的不对称氢化，以产生具有旋光活性的 β-氨基酸酯。容易获得的基于单齿八氢联萘酚的亚磷酰胺用作手性配体。E 异构体的对映选择性和产率非常好，而 Z 异构体的催化剂性能较差。重要的是，为了获得高对映选择性，必须在配体的 3,3' 位进行取代。在优化条件下实现了高达 94 % ee 的对映选择性。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites; a new combinatorial approach in asymmetric catalysisElectronic supplementary information (ESI) available: Experimental details. See http://www.rsc.org/suppdata/ob/b3/b302097e/
  作者：Diego Peña、Adriaan J. Minnaard、Jeroen A. F. Boogers、André H. M. de Vries、Johannes G. de Vries、Ben L. Feringa

  DOI：10.1039/b302097e

  日期：2003.3.27

  The combination of monodentate ligands in the rhodium-catalysed enantioselective hydrogenation enables a new approach when searching for the optimal activity and enantioselectivity in catalysis.

  在铑催化的对映选择性氢化中，单齿配体的结合为寻找最佳催化活性和对映选择性提供了一种新方法。