4-O-tosylferulic acid | 733015-03-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-O-tosylferulic acid
• 英文别名: 3-(3-Methoxy-4-(tosyloxy)phenyl)acrylic acid；3-[3-methoxy-4-(4-methylphenyl)sulfonyloxyphenyl]prop-2-enoic acid
• CAS: 733015-03-7
• 化学式: C₁₇H₁₆O₆S
• 分子量: 348.376
• InChiKey: OBIOXFLUCOHLTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-O-tosylferulic acid 、 (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.17h， 以100%的产率得到
  参考文献：
  名称：

  Total synthesis of (−)-incarvilline and (−)-incarvillateine

  摘要：

  An enantioselective, concise total synthesis of (-)-incarvilline and (-)-incarvillateine has been achieved in longest linear 9 steps (24.3% overall yield) and in 11 steps (16.5% overall yield) from (-)-carvone, respectively. The present synthesis features a notable Favorskii rearrangement of the O-protected chlorchydrin derivative of (-)-carvone to construct four of the five contiguous stereocenters on the bicyclic piperidine moiety and DMAP-catalyzed esterification of incarvilline with alpha-truxillic acid anhydride to generate incarvillateine skeleton. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.068

文献信息

• Total synthesis of (−)-incarvilline and (−)-incarvillateine
  作者：Fengying Zhang、Yanxing Jia

  DOI：10.1016/j.tet.2009.06.068

  日期：2009.8

  An enantioselective, concise total synthesis of (-)-incarvilline and (-)-incarvillateine has been achieved in longest linear 9 steps (24.3% overall yield) and in 11 steps (16.5% overall yield) from (-)-carvone, respectively. The present synthesis features a notable Favorskii rearrangement of the O-protected chlorchydrin derivative of (-)-carvone to construct four of the five contiguous stereocenters on the bicyclic piperidine moiety and DMAP-catalyzed esterification of incarvilline with alpha-truxillic acid anhydride to generate incarvillateine skeleton. (C) 2009 Elsevier Ltd. All rights reserved.