N,N-(diphenylmethyl)glycyl-glycine | 102016-70-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-(diphenylmethyl)glycyl-glycine
• 英文别名: N-(N,N-dibenzyl-glycyl)-glycine；N-(N,N-Dibenzyl-glycyl)-glycin；N,N-Dibenzyl-glycyl=>glycin；N,N-Dibenzyl-glycyl-glycin；2-[[2-(Dibenzylamino)acetyl]amino]acetic acid
• CAS: 102016-70-6
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: BFRAVIZQRQNRNC-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  534.4±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-(diphenylmethyl)glycyl-glycine 在 钯 、 溶剂黄146 作用下， 生成 双甘肽
  参考文献：
  名称：

  Velluz et al., Bulletin de la Societe Chimique de France, 1954, p. 1015

  摘要：

  DOI：
• 作为产物：
  描述：

  (二苄基氨基)乙酸 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 N,N-(diphenylmethyl)glycyl-glycine
  参考文献：
  名称：

  Non-depolarizing Neuromuscular Blocking Activity of Bisquaternary Amino Di- and Tripeptide Derivatives

  摘要：

  Herein we describe the synthesis of novel di- and tripeptide derivatives with two quaternary nitrogen groups attached and the biological testing of these compounds for neuromuscular blocking (NMB) activity in vitro and in vivo. The short peptide scaffold was selected because it offers potential for desired distance between the two pharmacophoric quaternary nitrogen groups, short duration of action, straightforward synthesis, and compatibility with an injectable formulation. From a small series of compounds 20c,e are identified as effective non-depolarizing NMB agents in vitro and in vivo in anesthetized cats and Rhesus monkeys with potencies similar to those of the clinical reference compounds rocuronium (4) and suxamethonium (2) (monkey ED90 = 0.68, 0.23, 0.16, 5.04 mu mol/kg, respectively). These new peptide derivatives 20c,e have similar potency and onset time but longer duration and slower recovery than the clinically used reference compounds. The structure-activity relationships described for this chemical series lead to the conclusion that the di- or tripeptide fragment can be regarded as an alternative template to the steroid or aliphatic ester of previously reported NMBs and within this tripeptide-derived series clog P correlates well with in vitro NMB activity.

  DOI：

  10.1021/jm0010062

文献信息

• Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination
  作者：Jing Wang、Wenji Wang、Xiongyu Yang、Jingwen Liu、Haizhou Huang、Mingxin Chang

  DOI：10.1007/s11426-022-1494-7

  日期：2023.2

  most efficient methods for amine synthesis. Herein we report a practical homogeneous DRA procedure utilizing iridium catalysis. Applying simple, readily available and inexpensive PPh3 and alike ligands along with iridium at a low loading, aldehydes and ketones reductively coupled with primary and secondary amines to efficiently form structurally and functionally diverse amine products, including a set

  直接还原胺化（DRA）是最有效的胺合成方法之一。在此，我们报告了一种利用铱催化的实用均相 DRA 程序。使用简单、容易获得且廉价的 PPh 3和类似的配体以及低负载量的铱、醛和酮与伯胺和仲胺还原偶联，有效地形成结构和功能多样的胺产品，包括一组药物和来自后期操作的化合物。反应条件异常温和且无添加剂，其中可以耐受氧气、水分、极性质子基团和多个其他官能团。对于目标产品，这种方法特别适用于提供多种可能的合成选择。10 克规模的合成进一步证明了该程序在实际胺合成中的潜力和前景。DFT 研究揭示了一种“外层”H 加成途径，其中π−π相互作用和氢键起着重要作用。