5-D-羟基丁基海因 | 5458-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-D-羟基丁基海因
• 中文别名: 5-(4-羟基丁基)咪唑烷-2,4-二酮
• 英文名称: 5-(4-hydroxybutyl)hydantoin
• 英文别名: hydroxybutyl-hydantoine；hydantoin；5-(4-hydroxy-butyl)-imidazolidine-2,4-dione；5-(4-Hydroxy-butyl)-imidazolidin-2,4-dion；5-(4-Hydroxybutyl)imidazolidine-2,4-dione
• CAS: 5458-06-0
• 化学式: C₇H₁₂N₂O₃
• mdl: MFCD00075682
• 分子量: 172.184
• InChiKey: SQKDMDCPJJTKKB-UHFFFAOYSA-N

物化性质

• 熔点：
  152-155°C
• 溶解度：
  可溶于甲醇（少量）、水（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-D-羟基丁基海因 在 氢溴酸 作用下， 反应 3.0h， 生成 5-德他-溴丁基海因
  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：

  四氢呋喃-2-甲醛 在 甲醇 、 sodium hydroxide 、 palladium on activated charcoal 、 碳酸氢铵 、 氯化铵 作用下， 生成 5-D-羟基丁基海因
  参考文献：
  名称：

  5-(2-tetrahydrofuryl) hydantoin and production therefrom of 5-(4-hydroxybutyl) hydantoin

  摘要：

  公开号：

  US02557904A1

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。
• Enzymatic synthesis of l -6-hydroxynorleucine
  作者：Ronald L. Hanson、Mark D. Schwinden、Amit Banerjee、David B. Brzozowski、Bang-Chi Chen、Bharat P. Patel、Clyde G. McNamee、Gus A. Kodersha、David R. Kronenthal、Ramesh N. Patel、Laszlo J. Szarka

  DOI：10.1016/s0968-0896(99)00158-3

  日期：1999.10

  L-6-Hydroxynorleucine, a key chiral intermediate used for synthesis of a vasopeptidase inhibitor, was prepared in 89% yield and > 99% optical purity by reductive amination of 2-keto-6-hydroxyhexanoic acid using glutamate dehydrogenase from beef liver. In an alternate process, racemic 6-hydroxynorleucine produced by hydrolysis of 5-(4-hydroxybutyl)hydantoin was treated with D-amino acid oxidase to prepare a

  L-6-羟基正亮氨酸，一种用于合成血管肽酶抑制剂的关键手性中间体，使用牛肉肝中的谷氨酸脱氢酶，通过2-胺基-6-羟基己酸的还原胺化反应，以89％的收率和> 99％的光学纯度制备。在另一种方法中，将5-（4-羟基丁基）乙内酰脲水解产生的外消旋6-羟基正亮氨酸用D-氨基酸氧化酶处理，以制备含有2-酮基6-羟基己酸和L-6-羟基正亮氨酸的混合物，然后还原胺化步骤将混合物完全转化为L-6-羟基正亮氨酸，产率为91％至97％，光学纯度为> 99％。
• Maimind et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2223,2227;engl.Ausg.S.2260,2264
  作者：Maimind et al.

  DOI：——

  日期：——
• Guivarch, Marcel; Gillonnier, Claude; Brunie, Jean-Claude, Bulletin de la Societe Chimique de France, 1980, vol. 2, # 1-2, p. 91 - 95
  作者：Guivarch, Marcel、Gillonnier, Claude、Brunie, Jean-Claude

  DOI：——

  日期：——
• Process Development in the Synthesis of the ACE Intermediate MDL 28,726
  作者：Stephen W. Horgan、David W. Burkhouse、Robert J. Cregge、David W. Freund、Michael LeTourneau、Alexey Margolin、Mark E. Webster、Daniel R. Henton、Kathy P. Barton、Robert C. Clouse、Michael A. DesJardin、Richard E. Donaldson、Neal J. Fetner、Christian T. Goralski、Gerald P. Heinrich、John F. Hoops、Robert T. Keaten、J. Russell McConnell、Mark A. Nitz、Sandra K. Stolz-Dunn

  DOI：10.1021/op970125x

  日期：1999.7.1

  MDL 28,726 is a key intermediate in the synthesis of the ACE inhibitors MDL 27,210A and MDL 100,240, An efficient nine-step synthesis of this tricyclic acid, which has three chiral centers, was developed beginning with 3,4-dihydro-2H-pyran. A key step in the synthesis features an enzyme-catalyzed resolution of the lithium salt of the N-trifluoroacetamide of (R,S)-6-hydroxynorleucine. All of the steps were optimized and completed in reactor equipment using environmentally acceptable processes. Process development of this route is described.