(S)-2,3-dihydro-2,4,6,7-tetramethyl-2-<(4-phenyl-1-piperidinyl)methyl>-5-benzofuranamine

• 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: (S)-2,3-dihydro-2,4,6,7-tetramethyl-2-<(4-phenyl-1-piperidinyl)methyl>-5-benzofuranamine
• 英文别名: (S)-(+)-5-amino-2,4,6,7-tetramethyl-2-(4-phenylpiperidinomethyl)-2,3-dihydrobenzo[b]furan；(S)-2,3-dihydro-2,4,6,7-tetramethyl-2-[(4-phenyl-1-piperidinyl)methyl]-5-benzofuranamine；(2S)-2,4,6,7-tetramethyl-2-[(4-phenylpiperidin-1-yl)methyl]-3H-1-benzofuran-5-amine
• 化学式: C₂₄H₃₂N₂O
• 分子量: 364.531
• InChiKey: OFJJFTDZPRQPBY-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-1-<<2,3-dihydro-2,4,6,7-tetramethyl-5-<(4-nitrophenyl)azo>benzofuran-2-yl>methyl>-4-phenylpiperidine 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以0.3%的产率得到(S)-2,3-dihydro-2,4,6,7-tetramethyl-2-<(4-phenyl-1-piperidinyl)methyl>-5-benzofuranamine
  参考文献：
  名称：

  Synthesis of TAK-218 using (R)-2-methylglycidyl tosylate as a chiral building block

  摘要：

  We performed an asymmetric synthesis of (S)-2,3-dihydro-2,4,6,7-tetramethyl-2-[(4-phenyl-1-piperidinyl)-methyl]-5-benzofuranamine dihydrochloride (TAK-218, 1), a compound used for the treatment of traumatic and ischemic central nervous system injuries. Oxirane 6, which was synthesized from (R)-2-methylglycidyl tosylate, was treated with aqueous trifluoroacetic acid to afford benzofuranmethanol 7 with inversion of stereochemistry at the stereogenic center. Compound 7 was converted into 1 with high enantiomeric excess in four steps. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00138-x

文献信息

• Crystalline salts of optically active aminocoumaran derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0601547A1

  公开（公告）日：1994-06-15

  A crystalline salt of an enantiomer of 5-amino-2,4,6,7-tetramethyl-2-(4-phenylpiperidinomethyl)-2,3-dihydrobenzo[b]furan which is stable and improved in solubility in water, is useful for an excellent lipidperoxide formation inhibitor.

  5-氨基-2,4,6,7-四甲基-2-（4-苯基哌啶甲基）-2,3-二氢苯并[b]呋喃对映体的结晶盐在水中的稳定性和溶解度都有所提高，是一种非常有用的过氧化脂质形成抑制剂。
• CYCLIC ETHER COMPOUNDS AS SODIUM CHANNEL MODULATORS
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0923575B1

  公开（公告）日：2003-03-12
• US5552552A
  申请人：——

  公开号：US5552552A

  公开（公告）日：1996-09-03
• US6172085B1
  申请人：——

  公开号：US6172085B1

  公开（公告）日：2001-01-09