(2R)-2-[[(1S,2R)-2-(methoxymethoxy)cyclopentyl]oxymethyl]oxirane | 864658-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R)-2-[[(1S,2R)-2-(methoxymethoxy)cyclopentyl]oxymethyl]oxirane
• CAS: 864658-65-1
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: HCBGCFQXFILIBZ-KXUCPTDWSA-N

物化性质

• 沸点：
  275.7±35.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-[[(1S,2R)-2-(methoxymethoxy)cyclopentyl]oxymethyl]oxirane 在 甲醇 、 正丁基锂 、 三氟化硼乙醚 、 sodium hydride 、 potassium carbonate 、 乙酰氯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.5h， 生成 (R)-1-[(1S,2R)-2-((R)-2-Hydroxy-pent-4-ynyloxy)-cyclopentyloxy]-dodec-4-yn-2-ol
  参考文献：
  名称：

  Synthesis of non-THF analogs of acetogenin toward simplified mimics

  摘要：

  Acetogenin analogs in which the bis-adjacent THF ring was replaced with an enantioselectively synthesized 1,2-cyclo-pentanediol bis-ether skeleton were synthesized to obtain simplified mimics, and their inhibitory effect on mitochondrial NADH-ubiquinone oxidoreductase (complex I) was examined. The results clearly demonstrate that the 1,2-cyclopentanediol bis-ether motif can substitute for the bis-THF ring while maintaining very potent inhibitory activity at the nanomolar level. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.150
• 作为产物：
  描述：

  (±)-反-1,2-环戊二醇 在 甲醇 、 ytterbium(III) chloride 、 potassium phosphate buffer 、 Pseudomanas fluorescens lipase (Amano AK) 、 sodium hydride 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 82.0h， 生成 (2R)-2-[[(1S,2R)-2-(methoxymethoxy)cyclopentyl]oxymethyl]oxirane
  参考文献：
  名称：

  Synthesis of non-THF analogs of acetogenin toward simplified mimics

  摘要：

  Acetogenin analogs in which the bis-adjacent THF ring was replaced with an enantioselectively synthesized 1,2-cyclo-pentanediol bis-ether skeleton were synthesized to obtain simplified mimics, and their inhibitory effect on mitochondrial NADH-ubiquinone oxidoreductase (complex I) was examined. The results clearly demonstrate that the 1,2-cyclopentanediol bis-ether motif can substitute for the bis-THF ring while maintaining very potent inhibitory activity at the nanomolar level. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.150

文献信息

• Synthesis of non-THF analogs of acetogenin toward simplified mimics
  作者：Daisuke Fujita、Naoya Ichimaru、Masato Abe、Masatoshi Murai、Takeshi Hamada、Takaaki Nishioka、Hideto Miyoshi

  DOI：10.1016/j.tetlet.2005.05.150

  日期：2005.8

  Acetogenin analogs in which the bis-adjacent THF ring was replaced with an enantioselectively synthesized 1,2-cyclo-pentanediol bis-ether skeleton were synthesized to obtain simplified mimics, and their inhibitory effect on mitochondrial NADH-ubiquinone oxidoreductase (complex I) was examined. The results clearly demonstrate that the 1,2-cyclopentanediol bis-ether motif can substitute for the bis-THF ring while maintaining very potent inhibitory activity at the nanomolar level. (c) 2005 Elsevier Ltd. All rights reserved.