methyl (1RS,4R)-2-oxo-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentanecarboxylate | 493039-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (1RS,4R)-2-oxo-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentanecarboxylate
• 英文别名: methyl (4R)-2-oxo-4-[(9-phenylfluoren-9-yl)amino]cyclopentane-1-carboxylate
• CAS: 493039-06-8
• 化学式: C₂₆H₂₃NO₃
• 分子量: 397.474
• InChiKey: ABFOPUWHHBYCDV-ITUIMRKVSA-N

物化性质

• 沸点：
  553.8±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1RS,4R)-2-oxo-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentanecarboxylate 在 10percent Pd/C 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 氢气 、 三乙胺 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 102.33h， 生成 (+)-(1S,2R,4R)-4-氨基-2-(羟甲基)-1-环戊醇
  参考文献：
  名称：

  Enantiospecific Synthesis of Carbapentostatins

  摘要：

  In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern, oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)carbapentostatin.

  DOI：

  10.1021/jo020612x
• 作为产物：
  描述：

  methyl (3S)-5-methoxycarbonyl-3-[N-(9-phenyl-9-fluorenyl)amino]-4-pentenoate 在 5percent Pt/C 2,2,6,6-tetramethylpiperidinyl-lithium 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、137.9 kPa 条件下， 反应 30.83h， 生成 methyl (1RS,4R)-2-oxo-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentanecarboxylate
  参考文献：
  名称：

  Enantiospecific Synthesis of Carbapentostatins

  摘要：

  In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern, oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)carbapentostatin.

  DOI：

  10.1021/jo020612x

文献信息

• Enantiospecific Synthesis of Carbapentostatins
  作者：Jonathan Z. Ho、Rafat M. Mohareb、Jin Hee Ahn、Tae Bo Sim、Henry Rapoport

  DOI：10.1021/jo020612x

  日期：2003.1.1

  In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern, oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)carbapentostatin.