benzyl 4-methyl-1-morpholino-1-oxopentan-2-ylcarbamate | 56414-80-3

• 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: benzyl 4-methyl-1-morpholino-1-oxopentan-2-ylcarbamate
• 英文别名: 4-(N-benzyloxycarbonyl-leucyl)-morpholine；benzyl N-(4-methyl-1-morpholin-4-yl-1-oxopentan-2-yl)carbamate
• CAS: 56414-80-3
• 化学式: C₁₈H₂₆N₂O₄
• 分子量: 334.415
• InChiKey: JRNWBMXUDPQVMI-UHFFFAOYSA-N

物化性质

• 沸点：
  522.4±50.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 4-methyl-1-morpholino-1-oxopentan-2-ylcarbamate 在 palladium on activated charcoal 氢气 作用下， 生成 4-methyl-1-morpholin-4-yl-1-oxopentan-2-amine
  参考文献：
  名称：

  有关抗生素肌动蛋白的研究。第三部分 酸酐-酰亚胺法合成肌动蛋白的结构类似物

  摘要：

  已经开发了具有高度立体选择性的合成路线，用于合成肌动蛋白（I）的结构类似物（XIII）。酸酐-酰亚胺法涉及序列（IIIb）+（V）→ [（VI）+（VII）] →（XI）→（XIII）。（±）-氨基酰胺（IIIb）产生具有相对构型（XIII）的（±）-异羟肟酸，并且L-氨基酰胺（X）产生具有绝对构型（XIII）的单一对映体。

  DOI：

  10.1039/p19750000830
• 作为产物：
  描述：

  氯甲酸苄酯 、 DL-亮氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 benzyl 4-methyl-1-morpholino-1-oxopentan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis, screening and docking of small heterocycles as Glycogen Phosphorylase inhibitors

  摘要：

  A series of morpholine substituted amino acids (phenylalanine, leucine, lysine and glutamic acid) was synthesized. A fragment-based screening approach was then used to evaluate a series of small heterocycles, including morpholine, oxazoline, dihydro-1,3-oxazine, tetrahydro-1,3-oxazepine, thiazoline, tetrahydro-1,3-pyrimidine, tetrahydro-1,3-diazepine and hexahydro-1H-benzimidazole, as potential inhibitors of Glycogen Phosphorylase a. Thiazoline 7 displayed an improved potency (IC50 of 25 μM) and had good LE and LELP values, as compared to heterocycles 1, 5, 9-13 and 19 (IC50 values of 1.1 mM-23.9 mM). A docking study using the crystal structure of human liver Glycogen Phosphorylase, provided insight into the interactions of heterocycles 5, 7, 9-13 and 19 with Glycogen Phosphorylase.

  DOI：

  10.1016/j.ejmech.2014.07.063

文献信息

• Studies concerning the antibiotic actinonin. Part III. Synthesis of structural analogues of actinonin by the anhydride–imide method
  作者：John P. Devlin、W. David Ollis、John E. Thorpe、Ronald J. Wood、Barbara J. Broughton、Peter J. Warren、Kenneth R. H. Wooldridge、Derek E. Wright

  DOI：10.1039/p19750000830

  日期：——

  A synthetic route, associated with a high degree of stereoselectivity, has been developed for the synthesis of structural analogues (XIII) of actinonin (I). The anhydride–imide method involves the sequence (IIIb)+(V)→[(VI)+(VII)]→(XI)→(XIII). (±)-Amino-amides (IIIb) yielded the (±)-hydroxamic acids with the relative configuration (XIII) and L-amino-amides (X) yielded single enantiomers with the absolute

  已经开发了具有高度立体选择性的合成路线，用于合成肌动蛋白（I）的结构类似物（XIII）。酸酐-酰亚胺法涉及序列（IIIb）+（V）→ [（VI）+（VII）] →（XI）→（XIII）。（±）-氨基酰胺（IIIb）产生具有相对构型（XIII）的（±）-异羟肟酸，并且L-氨基酰胺（X）产生具有绝对构型（XIII）的单一对映体。
• Synthesis, screening and docking of small heterocycles as Glycogen Phosphorylase inhibitors
  作者：Stephanie S. Schweiker、Wendy A. Loughlin、Anna S. Lohning、Maria J. Petersson、Ian D. Jenkins

  DOI：10.1016/j.ejmech.2014.07.063

  日期：2014.9

  A series of morpholine substituted amino acids (phenylalanine, leucine, lysine and glutamic acid) was synthesized. A fragment-based screening approach was then used to evaluate a series of small heterocycles, including morpholine, oxazoline, dihydro-1,3-oxazine, tetrahydro-1,3-oxazepine, thiazoline, tetrahydro-1,3-pyrimidine, tetrahydro-1,3-diazepine and hexahydro-1H-benzimidazole, as potential inhibitors of Glycogen Phosphorylase a. Thiazoline 7 displayed an improved potency (IC50 of 25 μM) and had good LE and LELP values, as compared to heterocycles 1, 5, 9-13 and 19 (IC50 values of 1.1 mM-23.9 mM). A docking study using the crystal structure of human liver Glycogen Phosphorylase, provided insight into the interactions of heterocycles 5, 7, 9-13 and 19 with Glycogen Phosphorylase.