isobutyl 2-cyclohexyl-2-hydroxy-2-phenylacetate | 1233868-78-4

• 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: isobutyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
• 英文别名: Ibuverine, (S)-；2-methylpropyl (2S)-2-cyclohexyl-2-hydroxy-2-phenylacetate
• CAS: 1233868-78-4
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: ARZBHIWSBXERKM-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-2-环己基-2-苯基乙醇酸 在 N-甲基哌啶 作用下， 以 甲苯 为溶剂， 反应 0.67h， 生成 isobutyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
  参考文献：
  名称：

  Formation of (S)-5-Cyclohexyl-5-phenyl-1,3-dioxolane-2,4-dione: A Key Intermediate in the Synthesis of (S)-Oxybutynin Hydrochloride

  摘要：

  The synthesis of the drug candidate (S)-oxybutynin hydrochloride 1 is described. The procedure involves initial activation of (5)cyclohexylmandelic acid 2, using isobutylchloroformate, followed by reaction of the resulting intermediate with 4-(diethylamino)but-2-yn-1-ol, 3. In this reaction, (S)-5-cyclohexyl-5-phenyl-1,3-dioxolane-2,4-dione 7 was identified as a key transient intermediate leading to 1. On the basis of the in situ IR spectroscopy data collected, the sequence of chemical events involved in the formation of intermediate 7, and its conversion to product and byproducts are described.

  DOI：

  10.1021/op100021w

文献信息

• Formation of (<i>S</i>)-5-Cyclohexyl-5-phenyl-1,3-dioxolane-2,4-dione: A Key Intermediate in the Synthesis of (<i>S</i>)-Oxybutynin Hydrochloride
  作者：Charles P. Vandenbossche、Philomen de Croos、Surendra P. Singh、Roger P. Bakale、Thomas R. Wagler

  DOI：10.1021/op100021w

  日期：2010.7.16

  The synthesis of the drug candidate (S)-oxybutynin hydrochloride 1 is described. The procedure involves initial activation of (5)cyclohexylmandelic acid 2, using isobutylchloroformate, followed by reaction of the resulting intermediate with 4-(diethylamino)but-2-yn-1-ol, 3. In this reaction, (S)-5-cyclohexyl-5-phenyl-1,3-dioxolane-2,4-dione 7 was identified as a key transient intermediate leading to 1. On the basis of the in situ IR spectroscopy data collected, the sequence of chemical events involved in the formation of intermediate 7, and its conversion to product and byproducts are described.