(S)-2,2-Dibenzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid | 146903-02-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-2,2-Dibenzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid
• 英文别名: (E,5S)-2,2-dibenzyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhex-3-enoic acid
• CAS: 146903-02-8
• 化学式: C₃₁H₃₅NO₄
• 分子量: 485.623
• InChiKey: KUDHFZJDUPGERB-CTNGAPNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2,2-Dibenzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 40.0h， 生成 Methyl (3S,4S,5S)-2,2-dibenzyl-5-<(tert-butoxycarbonyl)amino>-3,4-epoxy-6-phenylhexanoate
  参考文献：
  名称：

  Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres

  摘要：

  Novel Phe-Gly and Phe-Phe isosteres have been synthesized. Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid). Observed stereoselectivities of epoxidation appear to emanate from a cooperative coordination of the incoming peracid by the carbamate group and the more weakly coordinating allylic ester function.

  DOI：

  10.1021/jo00084a037
• 作为产物：
  描述：

  2,2-二苄基-1,3-丙二醇 在 jones' reagent 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 (S)-2,2-Dibenzyl-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid
  参考文献：
  名称：

  Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres

  摘要：

  Novel Phe-Gly and Phe-Phe isosteres have been synthesized. Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid). Observed stereoselectivities of epoxidation appear to emanate from a cooperative coordination of the incoming peracid by the carbamate group and the more weakly coordinating allylic ester function.

  DOI：

  10.1021/jo00084a037

文献信息

• Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres
  作者：Annika Jenmalm、Wei Berts、Yi-Lin Li、Kristina Luthman、Ingeborg Csoeregh、Uli Hacksell

  DOI：10.1021/jo00084a037

  日期：1994.3

  Novel Phe-Gly and Phe-Phe isosteres have been synthesized. Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid). Observed stereoselectivities of epoxidation appear to emanate from a cooperative coordination of the incoming peracid by the carbamate group and the more weakly coordinating allylic ester function.