(S)-4-hydroxy-4-<(9-phenylfluoren-9-yl)amino>butanoic acid methyl ester | 165058-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-4-hydroxy-4-<(9-phenylfluoren-9-yl)amino>butanoic acid methyl ester
• 英文别名: (S)-methyl 4-hydroxy-2-[(9-phenyl-9H-fluoren-9-yl)amino]butanoate；methyl (2S)-4-hydroxy-2-[(9-phenylfluoren-9-yl)amino]butanoate
• CAS: 165058-77-5
• 化学式: C₂₄H₂₃NO₃
• 分子量: 373.452
• InChiKey: AKYGGCRCWKVDIA-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-hydroxy-4-<(9-phenylfluoren-9-yl)amino>butanoic acid methyl ester 在 2-硝基苯基丝氰酸酯 、 三丁基膦 作用下， 以88%的产率得到(S)-2-<(9-phenylfluoren-9-yl)amino>-3-butenoic acid methyl ester
  参考文献：
  名称：

  Syntheses of Optically Active, Protected and Unprotected Vinylglycines.

  摘要：

  乙烯基甘氨酸（2）在酸性条件下会发生消旋化。通过酶水解 N-乙酰乙烯基甘氨酸 (5)，然后重结晶，从 2-HCl 中得到了光学纯度为 2 的乙烯基甘氨酸。(在酸性条件下，(S)-N-（甲氧羰基）乙烯基甘氨酸（6）的构型非常不稳定，因此无法从 2 中得到光学纯的 6。另一方面，从(S)-高丝氨酸合成了构型稳定的(S)-N-(9-苯基芴-9-基)乙烯基甘氨酸甲酯(9)。

  DOI：

  10.1248/cpb.42.1927
• 作为产物：
  描述：

  (2S)-α-methyl N-(9-phenyl-9H-fluoren-9-yl)aspartate 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以52%的产率得到(S)-4-hydroxy-4-<(9-phenylfluoren-9-yl)amino>butanoic acid methyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Homosphingosine Derivatives from l-Aspartic Acid

  摘要：

  The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived beta-ketophosphonate reagents and their Horner-Wadsworth-Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.

  DOI：

  10.1055/s-0029-1219081

文献信息

• Enantioselective Synthesis of Homosphingosine Derivatives from l-Aspartic Acid
  作者：Ari Koskinen、Sami Sauerland、Joel Castillo-Meléndez、Kalle Nättinen、Kari Rissanen

  DOI：10.1055/s-0029-1219081

  日期：2010.3

  The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived beta-ketophosphonate reagents and their Horner-Wadsworth-Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.
• Syntheses of Optically Active, Protected and Unprotected Vinylglycines.
  作者：Taisuke ITAYA、Shigeyuki SHIMIZU、Satoshi NAKAGAWA、Masatoshi MORISUE

  DOI：10.1248/cpb.42.1927

  日期：——

  Vinylglycine (2) has been shown to undergo racemization under acidic conditions. Optically pure 2 was obtained from 2·HCl by enzymatic hydrolysis through N-acetylvinylglycine (5), followed by recrystallization. (S)-N-(Methoxycarbonyl)vinylglycine (6) was configurationally so unstable under acidic conditions that 6 could not be obtained from 2 in an optically pure form. On the other hand, configurationally stable (S)-N-(9-phenylfluoren-9-yl)vinylglycine methyl ester (9) was synthesized from (S)-homoserine; 9 was hydrolyzed with sodium hydroxide to afford the carboxylic acid 10 of more than 99% ee.

  乙烯基甘氨酸（2）在酸性条件下会发生消旋化。通过酶水解 N-乙酰乙烯基甘氨酸 (5)，然后重结晶，从 2-HCl 中得到了光学纯度为 2 的乙烯基甘氨酸。(在酸性条件下，(S)-N-（甲氧羰基）乙烯基甘氨酸（6）的构型非常不稳定，因此无法从 2 中得到光学纯的 6。另一方面，从(S)-高丝氨酸合成了构型稳定的(S)-N-(9-苯基芴-9-基)乙烯基甘氨酸甲酯(9)。