(E)-2-azido-4-phenyl-3-buten-1-ol | 132803-71-5

• 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: (E)-2-azido-4-phenyl-3-buten-1-ol
• 英文别名: 2-Azido-4-phenylbut-3-en-1-ol；(E)-2-azido-4-phenylbut-3-en-1-ol
• CAS: 132803-71-5
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: ZVNMOZLMPFEOIZ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-azido-4-phenyl-3-buten-1-ol 在 二甲基硫 、 臭氧 作用下， 生成 2-azido-3-hydroxy-propionaldehyde
  参考文献：
  名称：

  .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

  摘要：

  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.

  DOI：

  10.1021/jo00012a015
• 作为产物：
  描述：

  反式肉桂醛 在 sodium azide 、 sodium hydride 作用下， 以 水 、 丙酮 为溶剂， 反应 3.17h， 生成 (E)-2-azido-4-phenyl-3-buten-1-ol
  参考文献：
  名称：

  .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

  摘要：

  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.

  DOI：

  10.1021/jo00012a015

文献信息

• Iminocyclitol inhibitors of hexoaminidase and glycosidase
  申请人：The Scripps Research Institute

  公开号：US06774140B1

  公开（公告）日：2004-08-10

  Designed iminocylitols that have potent inhibition activity with respect to hexominidases and glycosides are disclosed.

  披露了设计的亚氨基糖醇，它们对己糖苷酶和苷具有强大的抑制活性。
• 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。
• Claisen rearrangements of equilibrating allylic azides
  作者：Donald Craig、John W. Harvey、Alexander G. O'Brien、Andrew J. P. White

  DOI：10.1039/c1ob05972f

  日期：——

  Equilibrating mixtures of allylic azide-containing allylic alcohols or allylic 2-tolylsulfonylacetic esters undergo Johnson–Claisen or Ireland–Claisen rearrangement reactions to give unsaturated γ-azidoesters and -acids, respectively. Decarboxylation of the acids under basic conditions gives azidosulfones, with moderate to high diastereoselectivity.

  平衡的含烯丙基叠氮化物的烯丙基醇或烯丙基2-甲苯磺酰基磺酸酯的混合物会经历Johnson-Claisen或Ireland-Claisen重排反应，分别得到不饱和的γ-叠氮酯和-酸。在碱性条件下酸的脱羧得到叠氮基砜，具有中等至高的非对映选择性。
• [EN] IMINOCYCLITOL INHIBITORS OF HEXOAMINIDASE AND GLYCOSIDASE<br/>[FR] IMINOCYCLITOLS INHIBITEURS DE L'HEXOAMINIDASE ET DE LA GLYCOSIDASE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2000068194A1

  公开（公告）日：2000-11-16

  Designed iminocyclitols have potent inhibition activity with respect to hexoaminidases and glycosidases.

  设计的iminocyclitols具有对于葡萄糖胺酶和糖苷酶的强大抑制活性。
• Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues
  作者：Morwenna S.M. Pearson、Rim Ouled Saad、Thierry Dintinger、Hassen Amri、Monique Mathé-Allainmat、Jacques Lebreton

  DOI：10.1016/j.bmcl.2006.03.035

  日期：2006.6

  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.