(S)-2-[(2S,3S)-3-(chloromethyl)oxiran-2-yl]-2-methyl-1,4-dioxaspiro[4.4]nonane | 1057675-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-[(2S,3S)-3-(chloromethyl)oxiran-2-yl]-2-methyl-1,4-dioxaspiro[4.4]nonane
• 英文别名: (3S)-3-[(2S,3S)-3-(chloromethyl)oxiran-2-yl]-3-methyl-1,4-dioxaspiro[4.4]nonane
• CAS: 1057675-82-7
• 化学式: C₁₁H₁₇ClO₃
• 分子量: 232.707
• InChiKey: FTPWTXDLNRLAHT-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2S,3S)-3-(chloromethyl)oxiran-2-yl]-2-methyl-1,4-dioxaspiro[4.4]nonane 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(S)-1-[(S)-2-methyl-1,4-dioxaspiro[4.4]nonan-2-yl]prop-2-yn-1-ol
  参考文献：
  名称：

  The total synthesis and biological evaluation of nafuredin-γ and its analogues

  摘要：

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.066
• 作为产物：
  描述：

  [(2R,3S)-3-((S)-2-Methyl-1,4-dioxa-spiro[4.4]non-2-yl)-oxiranyl]-methanol 在 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以2.34 g的产率得到(S)-2-[(2S,3S)-3-(chloromethyl)oxiran-2-yl]-2-methyl-1,4-dioxaspiro[4.4]nonane
  参考文献：
  名称：

  The total synthesis and biological evaluation of nafuredin-γ and its analogues

  摘要：

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.066