(3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-aminophenylamino)piperidine-1-carboxylic acid tert-butyl ester | 1019207-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-aminophenylamino)piperidine-1-carboxylic acid tert-butyl ester
• CAS: 1019207-66-9
• 化学式: C₂₃H₄₁N₃O₃Si
• 分子量: 435.682
• InChiKey: OTGCNEVAQVUIFF-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  76.82
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 (3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-aminophenylamino)piperidine-1-carboxylic acid tert-butyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以100%的产率得到(3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-oxo-2,3-dihydrobenzimidazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A new synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (J-113397) and activity in a calcium mobilization assay

  摘要：

  A new chiral synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro-2H-benziinidazol-2-one (2, J-113397) was developed. J-113397 has a K-e = 0.85 nM in an ORL-1 calcium mobilization assay and is 89-, 887-, and 227-fold selective for the ORL-1 receptor relative to the p, 6, and K opioid receptors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.023
• 作为产物：
  描述：

  (3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-nitrophenylamino)piperidine-1-carboxylic acid tert-butyl ester 在 镍 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到(3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-aminophenylamino)piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A new synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (J-113397) and activity in a calcium mobilization assay

  摘要：

  A new chiral synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro-2H-benziinidazol-2-one (2, J-113397) was developed. J-113397 has a K-e = 0.85 nM in an ORL-1 calcium mobilization assay and is 89-, 887-, and 227-fold selective for the ORL-1 receptor relative to the p, 6, and K opioid receptors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.023