(S)-5-(4-methoxybenzyloxymethyl)cyclohex-2-enone | 1256355-94-8

• 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: (S)-5-(4-methoxybenzyloxymethyl)cyclohex-2-enone
• 英文别名: (5S)-5-[(4-methoxyphenyl)methoxymethyl]cyclohex-2-en-1-one
• CAS: 1256355-94-8
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: FEFRSFXAQBOTPU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1H-苯并三唑-1-甲醇 、 (S)-5-(4-methoxybenzyloxymethyl)cyclohex-2-enone 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以68%的产率得到(5S,6S)-6-hydroxymethyl-5-(4-methoxybenzyloxymethyl)cyclohex-2-enone
  参考文献：
  名称：

  Asymmetric synthesis of hydroxy-skipped bishomo-inositols as potential glycosidase inhibitors

  摘要：

  Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on alpha- and beta-glycosidases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.033
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 、 (5S)-5-hydroxymethyl-2-cyclohexen-1-one 在 CSA 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 以92%的产率得到(S)-5-(4-methoxybenzyloxymethyl)cyclohex-2-enone
  参考文献：
  名称：

  Asymmetric synthesis of hydroxy-skipped bishomo-inositols as potential glycosidase inhibitors

  摘要：

  Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on alpha- and beta-glycosidases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.033

文献信息

• Asymmetric synthesis of hydroxy-skipped bishomo-inositols as potential glycosidase inhibitors
  作者：Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2010.07.033

  日期：2010.9

  Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on alpha- and beta-glycosidases. (C) 2010 Elsevier Ltd. All rights reserved.