(1-Hydroxycyclohexyl)oxoacetic acid ethyl ester | 110890-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-Hydroxycyclohexyl)oxoacetic acid ethyl ester
• 英文别名: ethyl 1-hydroxy-α-oxocyclohexaneacetate；Aethoxycarbonyl-(1-hydroxy-cyclohexyl)-keton；Ethyl (1-hydroxycyclohexyl)(oxo)acetate；ethyl 2-(1-hydroxycyclohexyl)-2-oxoacetate
• CAS: 110890-49-8
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: KOHGARQMNITVFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1-Hydroxycyclohexyl)oxoacetic acid ethyl ester 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 (S)-ethyl 1-<2-(1-hydroxycyclohexyl)-1,2-dioxoethyl>-2-piperidinecarboxylate
  参考文献：
  名称：

  Design, synthesis, and kinetic evaluation of high-affinity FKBP ligands and the X-ray crystal structures of their complexes with FKBP12

  摘要：

  The design and synthesis of high-affinity FKBP12 ligands is described. These compounds potently inhibit the cis-trans-peptidylprolyl isomerase (rotamase) activity catalyzed by FKBP12 with inhibition constants (K(i,app)) as low as 1 nM, yet they possess remarkable structural simplicity relative to FK506 and rapamycin, from which they are conceptually derived. The atomic structures of three FKBP12-ligand complexes and of one unbound ligand were determined by X-ray crystallography and are compared to the FKBP12-FK506 and FKBP12-rapamycin complexes.

  DOI：

  10.1021/ja00075a008
• 作为产物：
  描述：

  1-氧杂螺[2.5]辛-2-甲酸乙酯 在 甲酸 、 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 (1-Hydroxycyclohexyl)oxoacetic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis, and kinetic evaluation of high-affinity FKBP ligands and the X-ray crystal structures of their complexes with FKBP12

  摘要：

  The design and synthesis of high-affinity FKBP12 ligands is described. These compounds potently inhibit the cis-trans-peptidylprolyl isomerase (rotamase) activity catalyzed by FKBP12 with inhibition constants (K(i,app)) as low as 1 nM, yet they possess remarkable structural simplicity relative to FK506 and rapamycin, from which they are conceptually derived. The atomic structures of three FKBP12-ligand complexes and of one unbound ligand were determined by X-ray crystallography and are compared to the FKBP12-FK506 and FKBP12-rapamycin complexes.

  DOI：

  10.1021/ja00075a008

文献信息

• Catalysis by di-n-butyltin oxide of a tertiary ketol rearrangement: synthesis of intermediates and analogues of valine and isoleucine biosynthesis
  作者：David H. G. Crout、Daniel L. Rathbone

  DOI：10.1039/c39870000290

  日期：——

  Di-n-butyltin oxide efficiently catalyses the rearrangement of 3-hydroxy-2-oxocarboxylic acid esters into the corresponding 2-hydroxy-3-oxo-esters, in a reaction that simulates the reversible rearrangement catalysed by the enzyme reductiosomerase.

  在模拟由酶还原异构酶催化的可逆重排的反应中，二正丁基氧化锡可有效地将3-羟基-2-氧代羧酸酯重排成相应的2-羟基-3-氧代酯。
• Oxidation of Alkynyl Ethers with Potassium Permanganate. A New Acyl Anion Equivalent for the Preparation of .alpha.-Keto Esters
  作者：John H. Tatlock

  DOI：10.1021/jo00124a049

  日期：1995.9
• Wisaksono,W.W.; Arens,J.F., Recueil des Travaux Chimiques des Pays-Bas, 1961, vol. 80, p. 846 - 848
  作者：Wisaksono,W.W.、Arens,J.F.

  DOI：——

  日期：——