(+/-)-(3E)-2-amino-4-phenylbut-3-en-1-ol | 132803-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-(3E)-2-amino-4-phenylbut-3-en-1-ol
• 英文别名: (E)-2-amino-4-phenyl-3-butene-1-ol；(E)-2-amino-4-phenyl-3-buten-1-ol；2-Amino-4-phenylbut-3-en-1-ol；(E)-2-amino-4-phenylbut-3-en-1-ol
• CAS: 132803-75-9
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: CKKVPCLNGXGAFO-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(3E)-2-amino-4-phenylbut-3-en-1-ol 在 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues

  摘要：

  Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient glycosidase inhibitory effects. The syntheses and biological evaluation of two new series of 5-deoxyadenophorine analogues in their racemic form are reported. The compounds 12e and 13d bearing a C-11 and C-7 alkyl chain, respectively, were found to be potent inhibitors of the beta-glucosidase from almond with W-i near to 60 mu M. The compounds 13a,d which possess a 3,4-cis stereochemistry were efficient on glucosidases but also on the beta-galactosidase, what was not observed with the 3,4-trans series 12. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.035
• 作为产物：
  描述：

  1-苯基-3-丁烯-1-醇 在 盐酸 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N-溴代乙酰胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (+/-)-(3E)-2-amino-4-phenylbut-3-en-1-ol
  参考文献：
  名称：

  N-溴乙酰胺介导的多米诺环化反应和消除均烯丙基三氯乙酰亚胺酯：一种合成1-溴-2-氨基-3-丁烯衍生物的新颖方法†

  摘要：

  报道了从均烯丙基三氯乙亚氨酸酯实际合成1-溴-2-氨基-3-丁烯衍生物。简单地将底物和N-溴乙酰胺的混合物在DMF中于90°C加热，将以中等至极好的收率得到所需的产物。该反应可以通过多米诺溴环化和消除途径进行。还研究了由1-溴-2-氨基-3-丁烯衍生物合成4,5-二氢恶唑。

  DOI：

  10.1039/c4ob01126k

文献信息

• Lewis Acid Catalyzed Intramolecular Allylic Substitution of Bis(trichloroacetimidates): A Versatile Approach to Racemic Unsaturated Amino Acids
  作者：Liene Grigorjeva、Aigars Jirgensons

  DOI：10.1002/ejoc.201100060

  日期：2011.5

  Lewis acid catalyzed cyclization of trichloroacetimidates derived from 1,4-butenediols and 1,5-butenediols was achieved to give 4-vinyl oxazolines and 4-vinyloxazines in good to excellent yields. The cyclization products were transformed to protected unsaturated α- and β-amino acids, thus demonstrating the novel approach to access these important classes of compounds.

  路易斯酸催化衍生自 1,4-丁烯二醇和 1,5-丁烯二醇的三氯乙酰亚胺酯的环化反应以良好至极好的产率得到 4-乙烯基恶唑啉和 4-乙烯基恶嗪。环化产物被转化为受保护的不饱和α-和β-氨基酸，从而展示了获取这些重要类别化合物的新方法。
• Catalytic, Enantioselective N-Acylation of Lactams and Thiolactams Using Amidine-Based Catalysts
  作者：Xing Yang、Valentina D. Bumbu、Peng Liu、Ximin Li、Hui Jiang、Eric W. Uffman、Lei Guo、Wei Zhang、Xuntian Jiang、K. N. Houk、Vladimir B. Birman

  DOI：10.1021/ja306766n

  日期：2012.10.24

  contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density

  与醇和胺不同，外消旋内酰胺和硫内酰胺不能通过酶促酰化或经典拆分直接拆分。由脒基催化剂，特别是 Cl-PIQ 2 和 BTM 3 促进的不对称 N-酰化，为这些有价值的化合物的动力学拆分提供了一种方便的方法，并且通常在该过程中实现了出色的对映选择性。密度泛函理论计算表明，反应通过内酰胺互变异构体的 N-酰化发生，阳离子-π 相互作用在内酰胺底物的手性识别中起关键作用。
• Indium-Mediated Stereoselective Synthesis of Truncated, 6- and 7-Carbon Sialic Acids
  作者：Wolf-Dieter Fessner、Mathias Warwel

  DOI：10.1055/s-2002-35564

  日期：——

  Several 6- and 7-carbon sialic acid derivatives were synthesized, without tedious protecting group manipulations, in high overall yields. A key step of the synthesis was the chain extension of suitable α-amino aldehyde derivatives by an indium-mediated addition of ethyl 2-(bromomethyl)acrylate. Under acidic reaction conditions, the corresponding extended enoates were obtained with high trans-stereoselectivity. Ozonolysis furnished the desired 4-acylamino-substituted hexulosonic and heptulosonic acids in free form for biochemical studies.

  我们合成了几种 6 碳和 7 碳的硅酸衍生物，无需繁琐的保护基操作，而且总产率很高。合成的一个关键步骤是通过铟介导的 2-（溴甲基）丙烯酸乙酯加成法对合适的δ-氨基醛衍生物进行链延伸。 在酸性反应条件下，以高反式-立体选择性获得了相应的扩展烯酸盐。 臭氧分解以游离形式产生了所需的 4-酰氨基取代的己酮磺酸和庚酮磺酸，可用于生化研究。
• .alpha.-Amino aldehyde equivalents as substrates for rabbit muscle aldolase: synthesis of 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
  作者：Rebecca R. Hung、Julie Ann Straub、George M. Whitesides

  DOI：10.1021/jo00012a015

  日期：1991.6

  This work examined the application of rabbit muscle aldolase (RAMA) to stereospecific carbon-carbon bond formation in the preparation of carbohydrates containing amino groups. Several alpha-amino aldehyde equivalents were evaluated as substrates for RAMA and for their synthetic utility in transformations following the aldol reaction. This methodology is illustrated by the syntheses of the pyrrolidine alkaloids 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R), 4(R)-dihydroxypyrrolidine. The kinetic resolution of racemic aldehydes by RAMA and mild methods for transforming the amino equivalents into the desired amines are discussed briefly.
• Chemoenzymatic synthesis of enantiomerically enriched aminoalkenols and glycosides thereof
  作者：Thomas Ziegler、Claus Jurisch

  DOI：10.1016/s0957-4166(00)00294-9

  日期：2000.8

  1-t-Butoxycarbonylamido-3-pentene-1-ol 3 and 2-azido-4-phenyl-3-butene-1-ol 4 were enantiomerically enriched by enzymatic acetylation using various lipases and esterases (CHIRAZYM) to give acetylated compounds 5 and 7, respectively. Compound 3 gave the best results (E = 94) with Candida antarctica A lipase (CHIRAZYM L-5), whereas 4 could not be separated into the enantiomers with satisfactory E values. The absolute configurations were proven for both compounds via independently prepared derivatives. Both enantiomers of 5, as well as racemic 7, were N-deblocked and condensed with octonic acid derivatives 14 to give the corresponding C-glycosides 17 and 22 after deprotection of the intermediates in good overall yield. Compound 4 was similarly condensed with glucose imidate 11 to give the diastereomeric O-glycosides 13 after deprotection. The latter glycosides were prepared as precursors for the generation of the corresponding aldehydes as substrates for aldolase catalyzed reactions. (C) 2000 Published by Elsevier Science Ltd.