(R)-1-benzoyl-2--aminocyclopentene | 144096-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-benzoyl-2--aminocyclopentene
• 英文别名: phenyl-[2-[[(1R)-1-phenylethyl]amino]cyclopenten-1-yl]methanone
• CAS: 144096-30-0
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: XBMUJVFTVXYYLC-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-benzoyl-2--aminocyclopentene 在 盐酸 、 六甲基磷酰三胺 、 甲基锂 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 (S)-2-benzoyl-5-methylcyclopentanone
  参考文献：
  名称：

  环状和无环手性β-烯氨基酮锂二价阴离子的立体选择性烷基化：（R）-或（S）-手性1,3-二酮的合成。

  摘要：

  在此通过环状和非环状手性β-烯氨基酮的不对称γ烷基化反应合成（R）-或（S）-手性1，3-二酮。烷基化需要有良好的收益率和高的地方去的HMPA / THF。1,3-二酮的两个纯对映异构体都可以通过简单水解这种方法获得的差向异构体β-烯氨基酮来形成，选择合适的合成策略。提出了不对称感应的解释。

  DOI：

  10.1016/s0957-4166(00)80373-0

文献信息

• A directed stereoselective aldol reaction: Simple synthesis of enantiopure δ-hydroxy-β-enamino ketones by condensation of homochiral β-enamino ketones with aldehydes and ketones
  作者：Cristina Cimarelli、Gianni Palmieri、Mercedes Camalli

  DOI：10.1016/0957-4166(96)00253-4

  日期：1996.7

  A simple synthesis of enantiopure anti-delta-Hydroxy-beta-enamino ketones 3 by condensation of homochiral lithium dianions derived from beta-enamino ketones 1('') with aldehydes and ketones is reported. The mechanism for the directed enantioselective aldol reaction was investigated. The anti delta-hydroxyenaminone 3 is obtained as the major diastereomer through an open transition state. In acidic conditions the delta-hydroxyenaminones 3 are cyclized to 4-imino-2,3-dihydropyranones 4 which are instable and isomerize spontaneously to gamma alkylidenenaminones 5. Copyright (C) 1996 Elsevier Science Ltd
• Stereoselective carbon—carbon bond formation: γ-alkylation of lithium dianion of chiral cyclic β-enamino ketones.
  作者：Giuseppe Bartoli、Cristina Cimarelli、Gianni Palmieri、Gianni Rafaiani

  DOI：10.1016/s0957-4166(00)80510-8

  日期：1992.6

  The gamma-alkylation of the chiral beta-enamino ketones (1) has been obtained with good yields and d.e. on the si face of the lithium dianion intermediate.
• Stereoselective preparation of enaminone lithium dianions: Synthesis of N,N-dimethylcarbamoylenaminones
  作者：Cristina Cimarelli、Gianni Palmieri、Mercedes Camalli

  DOI：10.1016/s0040-4020(97)00320-7

  日期：1997.5

  A simple regio- and stereoselective synthesis of N',N-dimethylcarbamoylenaminones 2 by acylation of enaminone lithium dianions 1 '' with N,N-dimethylcarbamoyl chloride is reported, The mechanism for the stereoselective preparation of the enaminone lithium dianions 1 '' and successive acylation was investigated. The carbamoylenaminones 2 are selectively cyclized to 4-amino-2-pyranones 3 or hydrolyzed to carbamoyl diketones 4 in acidic conditions. (C) 1997 Elsevier Science Ltd.