N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine hydrochloride | 184879-74-1

• 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-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine hydrochloride
• 英文别名: (2S)-3-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-2-[[2-(2,2,2-trifluoroacetyl)-3,4-dihydro-1H-isoquinolin-7-yl]sulfonylamino]propanoic acid;hydrochloride
• CAS: 184879-74-1
• 化学式: C₂₆H₂₈F₃N₃O₅S*ClH
• 分子量: 588.048
• InChiKey: HBTKZVRQPODQPU-BQAIUKQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine hydrochloride 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 1,2,5,6-Tetrahydro-3-pyridinylalanine: A Key Intermediate in the Preparation of Thrombin Inhibitor UK-239,326

  摘要：

  A short synthesis of N-protected 1,2,5,6-tetrahydro-3-pyridinylalanine derivatives (8-10) was accomplished using a simple procedure of quaternization of (3-pyridyl)alanine 6 with benzyl bromide followed by reduction with NaBH(4). Amino acid 10 was then converted to thrombin inhibitor UK-239,326 (2), which required the sequential functionalization of four amines to give four different functional groups (viz., sulfonamide, carboxamide, guanidine, and methylamine).

  DOI：

  10.1080/00397910701839210
• 作为产物：
  描述：

  N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine t-butyl ester 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以100%的产率得到N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine hydrochloride
  参考文献：
  名称：

  Synthesis of 1,2,5,6-Tetrahydro-3-pyridinylalanine: A Key Intermediate in the Preparation of Thrombin Inhibitor UK-239,326

  摘要：

  A short synthesis of N-protected 1,2,5,6-tetrahydro-3-pyridinylalanine derivatives (8-10) was accomplished using a simple procedure of quaternization of (3-pyridyl)alanine 6 with benzyl bromide followed by reduction with NaBH(4). Amino acid 10 was then converted to thrombin inhibitor UK-239,326 (2), which required the sequential functionalization of four amines to give four different functional groups (viz., sulfonamide, carboxamide, guanidine, and methylamine).

  DOI：

  10.1080/00397910701839210