methyl 2-(cyclohexyloxy)benzoate | 92864-17-0

• 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: methyl 2-(cyclohexyloxy)benzoate
• 英文别名: Methyl 2-cyclohexyloxybenzoate
• CAS: 92864-17-0
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: CGNXPXPTRWBGHN-UHFFFAOYSA-N

物化性质

• 沸点：
  340.4±15.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(cyclohexyloxy)benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 84.0h， 以100%的产率得到2-(cyclohexyloxy)benzoic acid
  参考文献：
  名称：

  Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition

  摘要：

  In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modi. cations on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using Clog D(7.4) values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50) = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.006
• 作为产物：
  描述：

  环己醇 、 水杨酸甲酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以85%的产率得到methyl 2-(cyclohexyloxy)benzoate
  参考文献：
  名称：

  超声用于酚类Mitsunobu反应中空间位阻底物的偶联。

  摘要：

  通过将高浓度与超声处理结合使用，可以实现酚与醇的Mitsunobu反应的大量增加，其中，任一种或两种都受空间阻碍。

  DOI：

  10.1021/jo0345751

文献信息

• Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition
  作者：Ippei Sato、Koichiro Morihira、Hiroshi Inami、Hirokazu Kubota、Tatsuaki Morokata、Keiko Suzuki、Yosuke Iura、Aiko Nitta、Takayuki Imaoka、Toshiya Takahashi、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2008.08.006

  日期：2008.9

  In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modi. cations on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using Clog D(7.4) values as the reference index of lipophilicity. This research led to the identification of N-(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50) = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1. (C) 2008 Elsevier Ltd. All rights reserved.
• Use of Sonication for the Coupling of Sterically Hindered Substrates in the Phenolic Mitsunobu Reaction
  作者：Salvatore D. Lepore、Yuanjun He

  DOI：10.1021/jo0345751

  日期：2003.10.1

  A vast rate increase in the Mitsunobu reaction of phenols with alcohols where either or both are sterically hindered has been achieved by the use of high concentration combined with sonication.

  通过将高浓度与超声处理结合使用，可以实现酚与醇的Mitsunobu反应的大量增加，其中，任一种或两种都受空间阻碍。