dimethyl (3R)-3-[N-(9-phenyl-9-fluorenyl)amino]adipate | 493039-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: dimethyl (3R)-3-[N-(9-phenyl-9-fluorenyl)amino]adipate
• 英文别名: dimethyl (3R)-3-[(9-phenylfluoren-9-yl)amino]hexanedioate
• CAS: 493039-05-7
• 化学式: C₂₇H₂₇NO₄
• 分子量: 429.516
• InChiKey: PAZFHNJKHBCTME-HXUWFJFHSA-N

物化性质

• 沸点：
  579.7±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (3R)-3-[N-(9-phenyl-9-fluorenyl)amino]adipate 在 10percent Pd/C 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 氢气 、 三乙胺 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 103.16h， 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 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 反应 30.0h， 以93%的产率得到dimethyl (3R)-3-[N-(9-phenyl-9-fluorenyl)amino]adipate
  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.