6-(2-methoxy-phenyl)-4-methyl-hex-4-enoic acid ethyl ester | 405938-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(2-methoxy-phenyl)-4-methyl-hex-4-enoic acid ethyl ester
• CAS: 405938-61-6
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: SXQLHNOYVKKUBG-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(2-methoxy-phenyl)-4-methyl-hex-4-enoic acid ethyl ester 在 4-甲基-3-吗啉酮 、 四氧化锇 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 15.0h， 以96%的产率得到(4S*,5S*)-6-(2-methoxy-phenyl)-4,5-dihydroxy-4-methyl-hexanoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective syntheses of syn 5-[1-hydroxy-2-(2-bromo-phenyl)-ethyl]-5-methyl-5H-furan-2-one and syn 5-[1-hydroxy-2-(2-methoxy-phenyl)-ethyl]-5-methyl-5H-furan-2-one

  摘要：

  The aldol condensation of 2-(tert-butyldimethylsilyloxy)-5-methyl-furan 4 with several phenylacetaldehydes led stereoselectively to the syn or the anti aldols under fluoride- or Lewis- acid-promoted conditions. However low yields are obtained due to the formation of the double condensation products or aldols at C-3 site. An alternative six-step synthetic sequence was developed to access the target molecules starting from 2-bromo-phenyl acetaldehyde 20 and 2-methoxy-phenyl acetaldehyde 21. Structural assessment of the aldol products was achieved by stereospecific transformations and H-1 NWR nOe experiments. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00975-9
• 作为产物：
  描述：

  (2-甲氧基苯基)乙醛 在 2,4-二硝基酚 、 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 6-(2-methoxy-phenyl)-4-methyl-hex-4-enoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective syntheses of syn 5-[1-hydroxy-2-(2-bromo-phenyl)-ethyl]-5-methyl-5H-furan-2-one and syn 5-[1-hydroxy-2-(2-methoxy-phenyl)-ethyl]-5-methyl-5H-furan-2-one

  摘要：

  The aldol condensation of 2-(tert-butyldimethylsilyloxy)-5-methyl-furan 4 with several phenylacetaldehydes led stereoselectively to the syn or the anti aldols under fluoride- or Lewis- acid-promoted conditions. However low yields are obtained due to the formation of the double condensation products or aldols at C-3 site. An alternative six-step synthetic sequence was developed to access the target molecules starting from 2-bromo-phenyl acetaldehyde 20 and 2-methoxy-phenyl acetaldehyde 21. Structural assessment of the aldol products was achieved by stereospecific transformations and H-1 NWR nOe experiments. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00975-9

文献信息

• Stereoselective syntheses of syn 5-[1-hydroxy-2-(2-bromo-phenyl)-ethyl]-5-methyl-5H-furan-2-one and syn 5-[1-hydroxy-2-(2-methoxy-phenyl)-ethyl]-5-methyl-5H-furan-2-one
  作者：Elena Redero、Celso Sandoval、Francisco Bermejo

  DOI：10.1016/s0040-4020(01)00975-9

  日期：2001.11

  The aldol condensation of 2-(tert-butyldimethylsilyloxy)-5-methyl-furan 4 with several phenylacetaldehydes led stereoselectively to the syn or the anti aldols under fluoride- or Lewis- acid-promoted conditions. However low yields are obtained due to the formation of the double condensation products or aldols at C-3 site. An alternative six-step synthetic sequence was developed to access the target molecules starting from 2-bromo-phenyl acetaldehyde 20 and 2-methoxy-phenyl acetaldehyde 21. Structural assessment of the aldol products was achieved by stereospecific transformations and H-1 NWR nOe experiments. (C) 2001 Elsevier Science Ltd. All rights reserved.