methyl (4S)-4-[N-(9-phenyl-9-fluorenyl)amino]-1-cyclopentenecarboxylate | 493039-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (4S)-4-[N-(9-phenyl-9-fluorenyl)amino]-1-cyclopentenecarboxylate
• 英文别名: methyl (4S)-4-[(9-phenylfluoren-9-yl)amino]cyclopentene-1-carboxylate
• CAS: 493039-08-0
• 化学式: C₂₆H₂₃NO₂
• 分子量: 381.474
• InChiKey: IYCDNMMHGPWSLA-FQEVSTJZSA-N

物化性质

• 沸点：
  524.6±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (4S)-4-[N-(9-phenyl-9-fluorenyl)amino]-1-cyclopentenecarboxylate 在 10percent Pd/C 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 、 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 92.0h， 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：

  dimethyl (3R)-3-[N-(9-phenyl-9-fluorenyl)amino]adipate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium tert-butylate 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 11.16h， 生成 methyl (4S)-4-[N-(9-phenyl-9-fluorenyl)amino]-1-cyclopentenecarboxylate
  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

• An Efficient Procedure for the Preparation of (1S,3R)- and (1S,3S)-1-Amino-3-(hydroxymethyl)cyclopentanes
  作者：Henry Rapoport、Yuewu Chen、Rafat M. Mohareb、Jin Hee Ahn、Tae Bo Sim、Jonathan Z. Ho

  DOI：10.1248/cpb.51.1153

  日期：——

  Enantiomerically pure (1S,3S)- and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanes have been efficiently synthesized from L-aspartic acid. The title compounds are isosteres of ribose and may be used to construct nucleoside analogs with important antiviral and antineoplastic activities as demonstrated by a concise total synthesis of (+)-4'-deoxycarbapentostatin nucleoside.

  对映体纯的（1S，3S）-和（1S，3R）-1-氨基-3-（羟甲基）环戊烷已由L-天冬氨酸有效合成。标题化合物是核糖的等排物，可用于构建具有重要抗病毒和抗肿瘤活性的核苷类似物，如简明的（+）-4'-deoxycarbapentostatin核苷的全合成所示。
• 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.