tert-butyl (S)-2-((2-(benzylsulfanyl)-6-phenylpyrimidin-4-yloxy)-methyl)pyrrolidine-1-carboxylate | 1035913-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: tert-butyl (S)-2-((2-(benzylsulfanyl)-6-phenylpyrimidin-4-yloxy)-methyl)pyrrolidine-1-carboxylate
• CAS: 1035913-26-8
• 化学式: C₂₇H₃₁N₃O₃S
• 分子量: 477.627
• InChiKey: BEZUUWRMMOTWAU-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.55
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-((2-(benzylsulfanyl)-6-phenylpyrimidin-4-yloxy)-methyl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以89%的产率得到2-(benzylsulfanyl)-6-phenyl-4-[((S)-pyrrolidin-2-yl)-methoxy]pyrimidine
  参考文献：
  名称：

  Synthesis of pyrimidinyl arylglycines through subsequent Mitsunobu and Petasis reactions

  摘要：

  The synthesis of highly functionalized pyrimidinyl arylglycines is presented. The highlight in our synthetic sequence includes selective O-alkylation of 2-(benzylsulfanyl)-4(3H)-pyrimidinones with N-Boc beta-aminoalcohols under Mitsunobu conditions, Petasis reaction with glyoxylic acid and phenylboronic acid and nucleophilic ipso-substitution of the activated sulfur with morpholine. The unexpected spontaneous Smiles rearrangement of several pyrimidinyl amines is also discussed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.035
• 作为产物：
  描述：

  N-Boc-L-脯氨醇 、 6-phenyl-2-benzylthiouracil 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以87%的产率得到tert-butyl (S)-2-((2-(benzylsulfanyl)-6-phenylpyrimidin-4-yloxy)-methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of pyrimidinyl arylglycines through subsequent Mitsunobu and Petasis reactions

  摘要：

  The synthesis of highly functionalized pyrimidinyl arylglycines is presented. The highlight in our synthetic sequence includes selective O-alkylation of 2-(benzylsulfanyl)-4(3H)-pyrimidinones with N-Boc beta-aminoalcohols under Mitsunobu conditions, Petasis reaction with glyoxylic acid and phenylboronic acid and nucleophilic ipso-substitution of the activated sulfur with morpholine. The unexpected spontaneous Smiles rearrangement of several pyrimidinyl amines is also discussed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.035