(R)-5-allyloxy-2-methylcyclohex-2-enone | 1048013-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-5-allyloxy-2-methylcyclohex-2-enone
• 英文别名: (5R)-2-methyl-5-prop-2-enoxycyclohex-2-en-1-one
• CAS: 1048013-35-9
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: BAYKMGHOAKCZNV-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-5-allyloxy-2-methylcyclohex-2-enone 、 (E,7S)-7-methoxy-N-(2-oxoethyl)dodec-4-enamide 、 碘甲烷 在 lithium diisopropyl amide 、 calcium sulfate 、 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 25.25h， 以41 mg的产率得到(4E,7S)-N-{(2S)-[(1R,6R)-6-allyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u
• 作为产物：
  描述：

  (1R,4R,6R)-4-allyloxy-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 在 三氟乙酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以86%的产率得到(R)-5-allyloxy-2-methylcyclohex-2-enone
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u

文献信息

• An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer
  作者：Jian-Peng Feng、Zi-Fa Shi、Yang Li、Jun-Tao Zhang、Xian-Liang Qi、Jie Chen、Xiao-Ping Cao

  DOI：10.1021/jo800876u

  日期：2008.9.1

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.