(7S,8R,9R)-7,9-Diphenyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid amide | 210306-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7S,8R,9R)-7,9-Diphenyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid amide
• CAS: 210306-53-9
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: PZYBCAYEPUEZEK-REPLKXPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (7S,8R,9R)-7,9-Diphenyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid amide 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以86%的产率得到2(e),6(e)-diphenyl-4-oxocyclohexane-1(e)-carboxamide
  参考文献：
  名称：

  On the Stereochemistry of Diaryl-Substituted Cyclohexanones Formed by Michael Reactions. Trans to Cis Isomerization of Their Ketals under Basic Conditions

  摘要：

  The stereochemistry of C-1-substituted 2,6-diphenylcyclohexan-4-ones 1-3 prepared by Michael reactions has been investigated. While preparations of these compounds have been reported over the past 70 years, in many instances the correct stereochemistry at C-2 (6) and, in some instances at C-1, was uncertain. We show here that in one case in which two identical substituents (CN) are present at C-1, it is possible to isomerize the initially formed trans isomer Id to the cis isomer 3f. When a cyano group and a dissimilar substituent are present at C-1, the initially formed trans isomer may be isomerized to the cis compound. The stereochemistry is vertified by NMR spectroscopy and by X-ray analysis. Reaction of the ethylene ketals (4 and 5) of these ketones with KOH in DMSO at elevated temperatures gives rise to cis products, and deuterium-labeling studies demonstrated the acidity of the benzylic hydrogen at C-2 (6). Isomerization was evident since the trans ketal 4a and the cis ketal 4b gave the same amide 6a. H-1 and C-13 NMR spectra provided conclusive evidence for the cis - trans rearrangement.

  DOI：

  10.1021/jo9801059
• 作为产物：
  描述：

  methyl 1-cyano-trans-2(e),6(a)-diphenyl-4,4-(ethylenedioxy)cyclohexane-1(e)-carboxylate 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以78%的产率得到(7S,8R,9R)-7,9-Diphenyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid amide
  参考文献：
  名称：

  On the Stereochemistry of Diaryl-Substituted Cyclohexanones Formed by Michael Reactions. Trans to Cis Isomerization of Their Ketals under Basic Conditions

  摘要：

  The stereochemistry of C-1-substituted 2,6-diphenylcyclohexan-4-ones 1-3 prepared by Michael reactions has been investigated. While preparations of these compounds have been reported over the past 70 years, in many instances the correct stereochemistry at C-2 (6) and, in some instances at C-1, was uncertain. We show here that in one case in which two identical substituents (CN) are present at C-1, it is possible to isomerize the initially formed trans isomer Id to the cis isomer 3f. When a cyano group and a dissimilar substituent are present at C-1, the initially formed trans isomer may be isomerized to the cis compound. The stereochemistry is vertified by NMR spectroscopy and by X-ray analysis. Reaction of the ethylene ketals (4 and 5) of these ketones with KOH in DMSO at elevated temperatures gives rise to cis products, and deuterium-labeling studies demonstrated the acidity of the benzylic hydrogen at C-2 (6). Isomerization was evident since the trans ketal 4a and the cis ketal 4b gave the same amide 6a. H-1 and C-13 NMR spectra provided conclusive evidence for the cis - trans rearrangement.

  DOI：

  10.1021/jo9801059