2,5-Dihydroxy-capronsaeure-nitril | 17264-36-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-Dihydroxy-capronsaeure-nitril
• 英文别名: 2,6-Dihydroxyhexanenitrile
• CAS: 17264-36-7
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: RJYTUGVEZRILPW-UHFFFAOYSA-N

物化性质

• 沸点：
  371.2±27.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-Dihydroxy-capronsaeure-nitril 在 氢溴酸 作用下， 以 乙醇 、 水 为溶剂， 反应 31.0h， 生成 5-(2,5-Dioxo-imidazolidin-4-yl)-pentanenitrile
  参考文献：
  名称：

  The biochemical basis for the deleterious effects of l-canavanine

  摘要：

  L-Canavanine, L-2-amino-4-(guanidinooxy)butyric acid, is a potentially toxic analogue of L-arginine. Canavanine-sensitive organisms activate and aminoacylate this non-protein amino acid and thereby create structurally aberrant, canavanine-containing proteins. Incorporation of canavanine into protein can alter the conformation and disrupt the function of the native macromolecule. Production of functionally impaired, canavanyl proteins affects developmental processes and contributes significantly to the expression of canavanine's potent antimetabolic properties in insects.

  DOI：

  10.1016/s0031-9422(00)95170-7
• 作为产物：
  描述：

  (+/-)-2-hydroxy-6-trityloxyhexanenitrile 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以54%的产率得到2,5-Dihydroxy-capronsaeure-nitril
  参考文献：
  名称：

  Enzymatic acylation reactions on ω-hydroxycyanohydrins

  摘要：

  The enzymatic acylation of certain omega-hydroxycyanohydrins protected a, the primary alcohol has been studied. The best enantioselectivities are obtained with Pseudomonas cepacia lipase (PSL-C) and Candida antarctica lipase A (CAL-A), for the omega-O-tritylated cyanohydrins. The effect of the protecting group in the enzymatic reactions has been studied using molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.134

文献信息

• Synthesis of 7,6‐Fused Bicyclic Lactams for Use as Beta‐Turn Mimics
  作者：Omar Morales、Wesley Seide、Samuel E. Watson

  DOI：10.1080/00397910500466496

  日期：2006.3.1

  Abstract An improved synthesis of the 7,6‐fused bicyclic lactam is presented starting from readily available chiral starting materials. (S)‐allylglycine is protected as the phthalimide derivative and coupled with (S)‐2‐amino‐6‐hydroxyhexanoic acid methyl ester. Oxidation of the hydroxyl group to the aldehyde followed by enamide synthesis and acyl iminium ion cyclization provide the bicyclic system

  摘要 7,6-稠合双环内酰胺的合成方法以现成的手性原料为起始原料。(S)-烯丙基甘氨酸被保护为邻苯二甲酰亚胺衍生物并与 (S)-2-氨基-6-羟基己酸甲酯偶联。将羟基氧化成醛，然后进行烯酰胺合成和酰基亚胺离子环化，以良好的总产率提供双环体系作为单一非对映异构体。
• SYNTHÈSES DE DÉRIVÉS DE LA LYSINE
  作者：Louis-Marie Babineau、Louis Berlinguet

  DOI：10.1139/v62-246

  日期：1962.8.1

  New N-ε-substituted lysines have been synthetized as follows: by condensing 5-δ-bromobutylhydantoin with different primary amines, 5-δ-alkylaminobutylhydantoins were obtained, the alkaline hydrolysis of which gave the corresponding N-ε-substituted lysines. N-α-Substituted hexahomoserines have also been prepared by acid hydrolysis of the reaction product between α,ε-dihydroxycaproic nitrile and primary amines. 5-Amino-5-carboxypentane sulphonamide has been prepared in the following way: 5-δ-bromobutylhydantoin was reacted with thiourea, and the resulting isothiouronium salt was oxidized with chlorine. Gaseous ammonia was then bubbled through an ethereal suspension of the 5-δ-chlorosulphonyl butylhydantoin and the resulting sulphonamide was hydrolyzed under pressure with barium hydroxide. 5-Amino-5-carboxypentane sulphonamide was then isolated and crystallized.

  新的N-ε-取代赖氨酸已经合成如下：通过将5-δ-溴丁基咪唑烷酮与不同的初级胺缩合，得到了5-δ-烷基氨基丁基咪唑烷酮，其碱水解产生相应的N-ε-取代赖氨酸。N-α-取代六羟基丝氨酸也通过α,ε-二羟基己腈与初级胺的反应产物的酸水解制备。5-氨基-5-羧基戊磺酰胺是通过以下方式制备的：5-δ-溴丁基咪唑烷酮与硫脲反应，生成的异硫脲盐经氯氧化。然后在5-δ-氯磺酰丁基咪唑烷酮的乙醚悬浮液中通入氨气，所得的磺酰胺在压力下与氢氧化钡水解。然后分离并结晶5-氨基-5-羧基戊磺酰胺。
• The biochemical basis for the deleterious effects of l-canavanine
  作者：Gerald A. Rosenthal

  DOI：10.1016/s0031-9422(00)95170-7

  日期：1991.1

  L-Canavanine, L-2-amino-4-(guanidinooxy)butyric acid, is a potentially toxic analogue of L-arginine. Canavanine-sensitive organisms activate and aminoacylate this non-protein amino acid and thereby create structurally aberrant, canavanine-containing proteins. Incorporation of canavanine into protein can alter the conformation and disrupt the function of the native macromolecule. Production of functionally impaired, canavanyl proteins affects developmental processes and contributes significantly to the expression of canavanine's potent antimetabolic properties in insects.
• Enzymatic acylation reactions on ω-hydroxycyanohydrins
  作者：Gonzalo de Gonzalo、Iván Lavandera、Rosario Brieva、Vicente Gotor

  DOI：10.1016/j.tet.2004.06.134

  日期：2004.11

  The enzymatic acylation of certain omega-hydroxycyanohydrins protected a, the primary alcohol has been studied. The best enantioselectivities are obtained with Pseudomonas cepacia lipase (PSL-C) and Candida antarctica lipase A (CAL-A), for the omega-O-tritylated cyanohydrins. The effect of the protecting group in the enzymatic reactions has been studied using molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.