2-methylcyclopropanecarbonyl fluoride | 247137-61-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methylcyclopropanecarbonyl fluoride
• 英文别名: 2-Methylcyclopropane-1-carbonyl fluoride
• CAS: 247137-61-7
• 化学式: C₅H₇FO
• 分子量: 102.108
• InChiKey: FZMVQLKLLCZTGY-UHFFFAOYSA-N

物化性质

• 沸点：
  99.9±7.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  X-206 potassium salt 、 2-methylcyclopropanecarbonyl fluoride 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 2.0h， 以54%的产率得到(2R)-2-[(2S,3S,6R)-6-[(2R,3S)-3-[(2R,5S,6R)-6-[[(2R,3S,5R,6R)-6-[(R)-[(2S,5S)-5-[(2R,3R,5S)-5-[(2R,5R,6S)-6-ethyl-5-hydroxy-5-methyloxan-2-yl]-2-hydroxy-3,5-dimethyloxolan-2-yl]-5-methyloxolan-2-yl]-(2-methylcyclopropanecarbonyl)oxymethyl]-6-hydroxy-3,5-dimethyloxan-2-yl]methyl]-6-hydroxy-5-methyloxan-2-yl]-2-hydroxybutyl]-3-methyloxan-2-yl]propanoic acid
  参考文献：
  名称：

  Use of the Potassium Ion as a Template for the Selective Derivatization of the Antibiotic X-206

  摘要：

  The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at, C(22) was investigated and the aquired knowledge used to achieve selective reactions on the benzyl ester 8 using a similar metal template protection.

  DOI：

  10.1021/jo9903151
• 作为产物：
  描述：

  2-甲基环丙羧酸 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-methylcyclopropanecarbonyl fluoride
  参考文献：
  名称：

  Use of the Potassium Ion as a Template for the Selective Derivatization of the Antibiotic X-206

  摘要：

  The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at, C(22) was investigated and the aquired knowledge used to achieve selective reactions on the benzyl ester 8 using a similar metal template protection.

  DOI：

  10.1021/jo9903151

文献信息

• Use of Acid Fluorides Increases the Scope of the Reductive Acylation of Esters
  作者：Yongda Zhang、Tomislav Rovis

  DOI：10.1021/ol049333h

  日期：2004.5.1

  The use of acyl fluorides in the Rychnovsky reductive acylation of esters allows a variety of esters to be converted to their corresponding alpha-acyloxy ethers in good to excellent yields, without the need to sacrifice an extra equiv of carboxylic acid functionality.
• Use of the Potassium Ion as a Template for the Selective Derivatization of the Antibiotic X-206
  作者：Anthony C. O'Sulliva、Fritz Struber、Steven V. Ley

  DOI：10.1021/jo9903151

  日期：1999.8.1

  The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at, C(22) was investigated and the aquired knowledge used to achieve selective reactions on the benzyl ester 8 using a similar metal template protection.