(R)-2-<<2-(methoxymethoxy)-3,4,6-trimethylphenyl>methyl>-2-methyloxirane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-<<2-(methoxymethoxy)-3,4,6-trimethylphenyl>methyl>-2-methyloxirane
• 英文别名: 2-[[2-(methoxymethoxy)-3,4,6-trimethylphenyl]methyl]-2-methyloxirane
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: IHQCEXNYIOMBJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.99
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-<<2-(methoxymethoxy)-3,4,6-trimethylphenyl>methyl>-2-methyloxirane 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 (S)-(2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl methanesulfonate
  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
• 作为产物：
  描述：

  2,3,5-三甲基苯酚 在 正丁基锂 、 三氟化硼乙醚 、 溴 、 sodium hydride 、 potassium carbonate 、 叔丁胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.33h， 生成 (R)-2-<<2-(methoxymethoxy)-3,4,6-trimethylphenyl>methyl>-2-methyloxirane
  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

• Synthesis of TAK-218 using (R)-2-methylglycidyl tosylate as a chiral building block
  作者：Kohji Fukatsu、Nobuhiro Fujii、Shigenori Ohkawa

  DOI：10.1016/s0957-4166(99)00138-x

  日期：1999.4

  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.