(2R)-2-benzyloxycyclohexanone | 880498-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-benzyloxycyclohexanone
• 英文别名: 2-(benzyloxy)cyclohexanone；(2R)-2-phenylmethoxycyclohexan-1-one
• CAS: 880498-21-5
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: DAAFSJHSNQOYMU-CYBMUJFWSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  319.9±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-benzyloxycyclohexanone 、 3,5-二甲基溴苯 在 magnesium 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以20%的产率得到
  参考文献：
  名称：

  Remarkable Effect of Subtle Structural Change of Chiral Pseudo-18-Crown-6 on Enantiomer-Selectivity in Complexation with Chiral Amino Alcohols

  摘要：

  Chiral receptors [(S,S)-1] and [(S,S,S,S)-2] having 1,2-dialkoxy-1-(3,5-dimethylphenyl)ethane and 1,2-dialkoxy-1-(3,5-dimethyl phenyl)cyclohexane as chiral building blocks, respectively, were prepared. Thermodynamic parameters of complexations of these and structurally related receptors [(S,S)-3] and [(S,S,S,S)-4] with 2-amino-1-propanol (5), 2-amino-2-phenylethanol (6), and 3-methylbutan-1-ol (7) in chloroform were determined. It was found that the host-guest systems that have same enantiomer-selectivity at 25 degrees C showed opposite selectivity in the enthalpy term. For example, complexations of both (SS)-1 and (SS)-3 with 5 are R-selective at 25 degrees C (Delta Delta G = 2.2 and 3.8 kJ mol(-1), respectively), whereas In terms of the enthalpy of complexation the former is S-selective (Delta Delta H = 22 kJ mol(-1)) but the latter is R-selective (Delta Delta H = 10 kJ mol(-1)).

  DOI：

  10.3987/com-05-s(k)42
• 作为产物：
  描述：

  trans-1,2-cyclohexandiol 在 lipase YS 氢氧化钾 、 jones' reagent 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 异丙醚 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 (2R)-2-benzyloxycyclohexanone
  参考文献：
  名称：

  Remarkable Effect of Subtle Structural Change of Chiral Pseudo-18-Crown-6 on Enantiomer-Selectivity in Complexation with Chiral Amino Alcohols

  摘要：

  Chiral receptors [(S,S)-1] and [(S,S,S,S)-2] having 1,2-dialkoxy-1-(3,5-dimethylphenyl)ethane and 1,2-dialkoxy-1-(3,5-dimethyl phenyl)cyclohexane as chiral building blocks, respectively, were prepared. Thermodynamic parameters of complexations of these and structurally related receptors [(S,S)-3] and [(S,S,S,S)-4] with 2-amino-1-propanol (5), 2-amino-2-phenylethanol (6), and 3-methylbutan-1-ol (7) in chloroform were determined. It was found that the host-guest systems that have same enantiomer-selectivity at 25 degrees C showed opposite selectivity in the enthalpy term. For example, complexations of both (SS)-1 and (SS)-3 with 5 are R-selective at 25 degrees C (Delta Delta G = 2.2 and 3.8 kJ mol(-1), respectively), whereas In terms of the enthalpy of complexation the former is S-selective (Delta Delta H = 22 kJ mol(-1)) but the latter is R-selective (Delta Delta H = 10 kJ mol(-1)).

  DOI：

  10.3987/com-05-s(k)42

文献信息

• Asymmetric Synthesis of O-Protected Acyloins Using Enoate Reductases: Stereochemical Control through Protecting Group Modification
  作者：Christoph K. Winkler、Clemens Stueckler、Nicole J. Mueller、Desiree Pressnitz、Kurt Faber

  DOI：10.1002/ejoc.201001042

  日期：2010.11

  O-Protected cyclic acyloins were obtained in nonracemic form through asymmetric bioreduction of α,β-unsaturated alkoxy ketones by using 11 different enoate reductases from the "Old Yellow Enzyme" family. The stereochemical outcome of the biotransformation could be switched by variation of the O-protecting group or by the ring size of the substrate, which allows access to both stereoisomers in up to

  通过使用来自“老黄酶”家族的 11 种不同烯酸还原酶对 α,β-不饱和烷氧基酮进行不对称生物还原，以非外消旋形式获得 O-保护的环状 acyloins。生物转化的立体化学结果可以通过 O-保护基团的变化或底物的环大小来切换，这允许以高达 97% ee 的比例获得两种立体异构体，而 α-烷氧基烯酮很容易被接受为底物， β-类似物未转化。总的来说，α-烷氧基烯酮代表了一种新型的黄素依赖性烯还原酶底物。
• Remarkable Effect of Subtle Structural Change of Chiral Pseudo-18-Crown-6 on Enantiomer-Selectivity in Complexation with Chiral Amino Alcohols
  作者：Keiji Hirose、Yoshito Tobe、Pakatip Aksharanandana、Michiko Suzuki、Kiyoshi Wada、Koichiro Naemura

  DOI：10.3987/com-05-s(k)42

  日期：——

  Chiral receptors [(S,S)-1] and [(S,S,S,S)-2] having 1,2-dialkoxy-1-(3,5-dimethylphenyl)ethane and 1,2-dialkoxy-1-(3,5-dimethyl phenyl)cyclohexane as chiral building blocks, respectively, were prepared. Thermodynamic parameters of complexations of these and structurally related receptors [(S,S)-3] and [(S,S,S,S)-4] with 2-amino-1-propanol (5), 2-amino-2-phenylethanol (6), and 3-methylbutan-1-ol (7) in chloroform were determined. It was found that the host-guest systems that have same enantiomer-selectivity at 25 degrees C showed opposite selectivity in the enthalpy term. For example, complexations of both (SS)-1 and (SS)-3 with 5 are R-selective at 25 degrees C (Delta Delta G = 2.2 and 3.8 kJ mol(-1), respectively), whereas In terms of the enthalpy of complexation the former is S-selective (Delta Delta H = 22 kJ mol(-1)) but the latter is R-selective (Delta Delta H = 10 kJ mol(-1)).