(4R)-3-((4'R,5'R)-cyclohexene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone | 287178-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-3-((4'R,5'R)-cyclohexene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone
• 英文别名: (4R)-4-benzyl-3-[(1R,6R)-6-methylcyclohex-3-ene-1-carbonyl]-1,3-oxazolidin-2-one
• CAS: 287178-29-4
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: VAODXLAMUKUHMM-FVQBIDKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-3-((4'R,5'R)-cyclohexene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以20.2 g的产率得到(-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid
  参考文献：
  名称：

  Enantioselective Synthesis of Ceralure B1, Ethyl cis-5-Iodo-trans-2-methylcyclohexane-1-carboxylate

  摘要：

  Ethyl (1R, 2R, SR)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)00219-2
• 作为产物：
  描述：

  (R)-4-苄基-2-噁唑烷酮 在 正丁基锂 、 加尔万氧基自由基 、 氯化二乙基铝 作用下， 以 二氯甲烷 为溶剂， 生成 (4R)-3-((4'R,5'R)-cyclohexene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective Synthesis of Ceralure B1, Ethyl cis-5-Iodo-trans-2-methylcyclohexane-1-carboxylate

  摘要：

  Ethyl (1R, 2R, SR)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)00219-2

文献信息

• Enantioselective Synthesis of Ceralure B1, Ethyl cis-5-Iodo-trans-2-methylcyclohexane-1-carboxylate
  作者：Andre S. Raw、Eric B. Jang

  DOI：10.1016/s0040-4020(00)00219-2

  日期：2000.5

  Ethyl (1R, 2R, SR)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. Published by Elsevier Science Ltd.