1,1-dimethylethyl (1R,2R)-N-[2-hydroxy-1-(4-methoxyphenyl)-3-butenyl]carbamate | 635313-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1-dimethylethyl (1R,2R)-N-[2-hydroxy-1-(4-methoxyphenyl)-3-butenyl]carbamate
• 英文别名: tert-butyl N-[(1R,2R)-2-hydroxy-1-(4-methoxyphenyl)but-3-enyl]carbamate
• CAS: 635313-39-2
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: CXSXXVRTQRCLGV-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (1R,2R)-N-[2-hydroxy-1-(4-methoxyphenyl)-3-butenyl]carbamate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97.3%的产率得到(4R,5R)-5-(ethenyl)-4-(4-methoxyphenyl)-2-oxazolidinone
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

  摘要：

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

  DOI：

  10.1081/scc-120022181
• 作为产物：
  描述：

  (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate 在 sodium tetrahydroborate 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 1,1-dimethylethyl (1R,2R)-N-[2-hydroxy-1-(4-methoxyphenyl)-3-butenyl]carbamate
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

  摘要：

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

  DOI：

  10.1081/scc-120022181

文献信息

• Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone
  作者：A. Ravi Kumar、G. Bhaskar、A. Madhan、B. Venkateswara Rao

  DOI：10.1081/scc-120022181

  日期：2003.1.8

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.