2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone | 1620387-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone
• 英文别名: 2-OBO-cyclopentanone；2-(4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentan-1-one；2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentan-1-one
• CAS: 1620387-58-7
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: ZYCRVYZFCPNTEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone 在 lithium aluminium tetrahydride 、 正丁基锂 、 水 、 potassium carbonate 、 4-叔丁基苯硫酚 、 三苯基膦 、 lithium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲基叔丁基醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.25h， 生成 (E)-2-(2-(((benzyloxy)carbonyl)amino)-1-fluoroethylidene)cyclopentane-1-carboxylic acid
  参考文献：
  名称：

  E-Selective Horner–Wadsworth–Emmons reaction of 2-OBO-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(E)-CFC]-Pro-OH dipeptide isostere

  摘要：

  The Horner-Wadsworth-Emmons reactions of ethyl 2-fluoro-2-diethylphosphonoacetate with 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone (2-OBO-cyclopentanone) using n-butyl-lithium furnished the corresponding tetra-substituted fluoroolefin in an E-selective manner (E:Z = 95:5). A facile synthesis of rac-N-Cbz-Gly-Psi[(E)-CF=C]-Pro-OH as a dipeptide isostere was achieved based on the E-selective Horner-Wadsworth-Emmons reaction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.063
• 作为产物：
  描述：

  2-羟基环戊基羧酸甲酯 在 三氟化硼乙醚 、 三氧化硫吡啶 、 caesium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone
  参考文献：
  名称：

  E-Selective Horner–Wadsworth–Emmons reaction of 2-OBO-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(E)-CFC]-Pro-OH dipeptide isostere

  摘要：

  The Horner-Wadsworth-Emmons reactions of ethyl 2-fluoro-2-diethylphosphonoacetate with 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone (2-OBO-cyclopentanone) using n-butyl-lithium furnished the corresponding tetra-substituted fluoroolefin in an E-selective manner (E:Z = 95:5). A facile synthesis of rac-N-Cbz-Gly-Psi[(E)-CF=C]-Pro-OH as a dipeptide isostere was achieved based on the E-selective Horner-Wadsworth-Emmons reaction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.063

文献信息

• E-Selective Horner–Wadsworth–Emmons reaction of 2-OBO-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(E)-CFC]-Pro-OH dipeptide isostere
  作者：Shigeki Sano、Tomoya Matsumoto、Michiyasu Nakao

  DOI：10.1016/j.tetlet.2014.06.063

  日期：2014.8

  The Horner-Wadsworth-Emmons reactions of ethyl 2-fluoro-2-diethylphosphonoacetate with 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone (2-OBO-cyclopentanone) using n-butyl-lithium furnished the corresponding tetra-substituted fluoroolefin in an E-selective manner (E:Z = 95:5). A facile synthesis of rac-N-Cbz-Gly-Psi[(E)-CF=C]-Pro-OH as a dipeptide isostere was achieved based on the E-selective Horner-Wadsworth-Emmons reaction. (C) 2014 Elsevier Ltd. All rights reserved.