2,2,2-Trifluoro-N-((S)-1-{(S)-1-formyl-2-[4-(3-methyl-but-2-enyloxy)-phenyl]-ethyl}-8-oxo-1-aza-spiro[4.5]dec-3-yl)-N-methyl-acetamide | 361520-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 2,2,2-Trifluoro-N-((S)-1-{(S)-1-formyl-2-[4-(3-methyl-but-2-enyloxy)-phenyl]-ethyl}-8-oxo-1-aza-spiro[4.5]dec-3-yl)-N-methyl-acetamide
• 英文别名: 2,2,2-trifluoro-N-methyl-N-[(3S)-1-[(2S)-1-[4-(3-methylbut-2-enoxy)phenyl]-3-oxopropan-2-yl]-8-oxo-1-azaspiro[4.5]decan-3-yl]acetamide
• CAS: 361520-03-8
• 化学式: C₂₆H₃₃F₃N₂O₄
• 分子量: 494.554
• InChiKey: RIDXLVYMFLWNTL-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-N-((S)-1-{(S)-1-formyl-2-[4-(3-methyl-but-2-enyloxy)-phenyl]-ethyl}-8-oxo-1-aza-spiro[4.5]dec-3-yl)-N-methyl-acetamide 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (+)-TAN1251C
  参考文献：
  名称：

  Total Synthesis of Tricyclic Azaspirane Derivatives of Tyrosine:  FR901483 and TAN1251C

  摘要：

  A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.

  DOI：

  10.1021/ja016030z
• 作为产物：
  描述：

  L-酪氨酸 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 platinum(IV) oxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 2,2,2-三氟乙醇 、 碘苯二乙酸 、 氢气 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 、 caesium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 氯仿 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， -78.0~50.0 ℃ 、101.33 kPa 条件下， 反应 90.0h， 生成 2,2,2-Trifluoro-N-((S)-1-{(S)-1-formyl-2-[4-(3-methyl-but-2-enyloxy)-phenyl]-ethyl}-8-oxo-1-aza-spiro[4.5]dec-3-yl)-N-methyl-acetamide
  参考文献：
  名称：

  Total Synthesis of Tricyclic Azaspirane Derivatives of Tyrosine:  FR901483 and TAN1251C

  摘要：

  A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.

  DOI：

  10.1021/ja016030z

文献信息

• Total Synthesis of Tricyclic Azaspirane Derivatives of Tyrosine:  FR901483 and TAN1251C
  作者：Malika Ousmer、Norbert A. Braun、Claude Bavoux、Monique Perrin、Marco A. Ciufolini

  DOI：10.1021/ja016030z

  日期：2001.8.1

  A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.