N-Benzyloxycarbonylglycine imidazolide | 22586-32-9

• 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: N-Benzyloxycarbonylglycine imidazolide
• 英文别名: Z-Glycinimidazolid；N-Benzyloxycarbonyl-glycyl-imidazolid；1-Carbobenzoxyaminoacetyl-imidazol；1-(N-benzyloxycarbonyl-glycyl)-1H-imidazole；benzyl N-(2-imidazol-1-yl-2-oxoethyl)carbamate
• CAS: 22586-32-9
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: CKAYACNZSQBAEN-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Benzyloxycarbonylglycine imidazolide 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 73.5h， 生成 dibenzyl ((((((((pentane-1,5-diylbis(azanediyl))bis(carbonyl))bis(1-propyl-1H-pyrrole-5,3-diyl))bis(azanediyl))bis(carbonyl))bis(1-propyl-1H-pyrrole-5,3-diyl))bis(azanediyl))bis(2-oxoethane-2,1-diyl))dicarbamate
  参考文献：
  名称：

  摘要：

  Bis-Netropsins with the C-ends of their netropsin fragments tethered via tetra- or pentamethylene linkers and with Gly or L-Lys-Gly residues on their N-ends were synthesized. The footprinting technique was used to study the specificity of bis-netropsin binding to the specially constructed DNA fragments containing various clusters of A . T pairs. It was found that the tinker length affects the binding of bis-netropsins, with the tetramethylene tinker providing better protection than the pentamethylene tinker. It was shown that the newly synthesized bis-netropsins bind tighter to the 5'-A(4)T(4)-3' sequence, whereas the bis-netropsin with a linker between the netropsin N-ends binds better to 5'-T(4)A(4)-3' sequences.

  DOI：

  10.1023/a:1021241515208
• 作为产物：
  描述：

  咪唑 、 N-苄氧羰基甘氨酸 在 氯化亚砜 作用下， 生成 N-Benzyloxycarbonylglycine imidazolide
  参考文献：
  名称：

  Synthesis and biological properties of choline esters of amino acids

  摘要：

  DOI：

  10.1007/bf00765209

文献信息

• An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives
  作者：Rita Mocci、Lidia De Luca、Francesco Delogu、Andrea Porcheddu

  DOI：10.1002/adsc.201600350

  日期：2016.10.6

  An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high‐energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies

  提出了通过高能机械化学活化将羧酸简单，经济地转化为异羟肟酸衍生物的方法。该球磨方法论已应用于多种羧酸，大大改善了与此类分子相关的纯化问题，而这些问题仍然是经典方法学的主要瓶颈之一。
• Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides
  作者：Uroš Grošelj、Amalija Golobič、Damijan Knez、Martina Hrast、Stanislav Gobec、Sebastijan Ričko、Jurij Svete

  DOI：10.1007/s11030-016-9668-9

  日期：2016.8

  The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the construction of a library of amides using various aliphatic, aromatic, and amino acid-derived coupling partners using BPC and CDI as activating agents. Amide

  从市售的（1 S）-（+）-10-樟脑磺酸开始，已经实现了两种新颖的（+）-异马来酸衍生的胺的合成。在使用各种脂肪族，芳香族和氨基酸衍生的偶联伙伴（使用BPC和CDI作为活化剂）构建酰胺库的过程中，已将新型胺以及（+）-异马来酸用作结构单元。已对酰胺衍生物进行了针对几种酶的分析，这些酶具有开发新药来对抗细菌感染和阿尔茨海默氏病的潜力。化合物20c和20e显示出对人类丁酰胆碱酯酶\（（h \ hbox BChE}）\）  （\（\ hbox IC} _ 50} \）的选择性亚微摩尔抑制作用值分别为\（0.80 \，\ pm 0.05 \）和\（0.25 \，\ pm 0.02 \，\ upmu} \ hbox M} \）。
• Ru-Catalyzed Asymmetric Hydrogenation of γ-Heteroatom Substituted β-Keto Esters
  作者：Weizheng Fan、Wanfang Li、Xin Ma、Xiaoming Tao、Xiaoming Li、Ying Yao、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/jo201822k

  日期：2011.11.18

  A series of enantiomerically pure γ-heteroatom substituted β-hydroxy esters were synthesized with high enantioselectivities (up to 99.1% ee) by hydrogenation of γ-heteroatom substituted β-keto esters in the presence of Ru-(S)-SunPhos catalyst. These asymmetric hydrogenations provide key building blocks for a variety of naturally occurring and biologically active compounds.

  在Ru- （S）-SunPhos催化剂存在下，通过氢化γ-杂原子取代的β-酮酯，合成了一系列具有高对映选择性（高达99.1％ee）的对映体纯的γ-杂原子取代的β-羟基酯。这些不对称氢化为各种天然存在的生物活性化合物提供了重要的组成部分。
• Synthesis of Novel 3D-Rich α-Amino Acid-Derived 3-Pyrazolidinones
  作者：Jaka Glavač、Georg Dahmann、Franc Požgan、Sebastijan Ričko、Bogdan Štefane、Jurij Svete、Uroš Grošelj

  DOI：10.17344/acsi.2017.3438

  日期：2017.12.15

  Synthetic approaches towards novel 3-pyrazolidinone derivatives functionalized at positions N(1) and/or C(5) were studied. 5-Aminoalkyl-3-pyrazolidinones were prepared in four steps from N-protected glycines via Masamune-Claisen homologation, reduction, O-mesylation, and cyclisation with a hydrazine derivative. The free amines were prepared by acidolytic deprotection. Title compound was also prepared

  研究了在位置N（1）和/或C（5）上官能化的新型3-吡唑烷酮衍生物的合成方法。由N-保护的甘氨酸通过Masamune-Claisen同源化，还原，O-甲磺酰化和与肼衍生物的环化反应，在四个步骤中制备5-氨基烷基-3-吡唑烷酮。通过酸解脱保护制备游离胺。还通过用水合肼对N-Boc-吡咯啉-2（5H）-1进行“环切换”转化来制备标题化合物。对5-（N-烷基-N-Cbz-氨基甲基）吡唑烷-3-酮进行氢解脱保护，然后与1,1'-羰基二咪唑（CDI）环合，得到两个新的全氢咪唑并[1,5-b]吡唑代表，是几乎未开发的杂环系统。3-氧代吡唑烷-5-羧酸的酰胺化以中等收率得到相应的羧酰胺。由（S）-AlaOMe和（S）-ProOMe获得的非对映体非外消旋羧酰胺通过MPLC分离。
• [EN] METHOD FOR PREPARING 2-AMINO-N-(2,2,2-TRIFLUOROETHYL) ACETAMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 2-AMINO-N-(2,2,2-TRIFLUOROÉTHYL)ACÉTAMIDE
  申请人：DU PONT

  公开号：WO2012047543A1

  公开（公告）日：2012-04-12

  Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2- trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.

  揭示了制备化合物1和1A的方法。第一种方法利用苄基氨基甲酸酯保护基和Formula 4的中间体。第二种方法利用叔丁基氨基甲酸酯保护基和Formula 7的中间体。第三种方法利用二苄胺保护基。还揭示了一种化合物，苯甲基N-[2-氧代-2-[(2,2,2-三氟乙基)氨基]乙基]氨基甲酸酯（Formula 4的化合物）。此外还揭示了一种从Formula 15的化合物和Formula 1或1A的化合物制备Formula 14的方法。