(5R)-1-tert-butoxycarbonyl-3,5-dimethyl-3-pyrrolin-2-one | 198976-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (5R)-1-tert-butoxycarbonyl-3,5-dimethyl-3-pyrrolin-2-one
• 英文别名: tert-butyl (2R)-2,4-dimethyl-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 198976-14-6
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: MSBYTSWQCZJNBS-MRVPVSSYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  267.5±33.0 °C(predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-1-tert-butoxycarbonyl-3,5-dimethyl-3-pyrrolin-2-one 在 lithium hydroxide 、 lithium aluminium deuteride 、 氘代甲醇-d 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 22.0h， 生成 methyl (2S,3S,4R)-4-(tert-butoxycarbonylamino)-3-deutero-2-methylpentanoate
  参考文献：
  名称：

  Conformational analysis of 4-amido-2,4-dimethylbutyric acid derivatives

  摘要：

  研究发现，同系和反系 4-氨基-2,4-二甲基丁酸衍生物 5 和 6 都有一个氨基与分子主链同向的构象。在反系列（6）中，一种单一的构象占主导地位，其中的酸羰基也与主链呈高位。在同系列（5）中，C-2-C-3 键的两个局部构象占主导地位。

  DOI：

  10.1039/a910179i
• 作为产物：
  描述：

  (R)-2-(叔丁氧羰基氨基)丙醛 在 4-二甲氨基吡啶 、 18-冠醚-6 、 二碳酸二叔丁酯 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 (5R)-1-tert-butoxycarbonyl-3,5-dimethyl-3-pyrrolin-2-one
  参考文献：
  名称：

  Synthesis of the C₂₆−C₃₂ Oxazole Fragment of Calyculin C:  A Test Case for Oxazole Syntheses

  摘要：

  The synthesis of the C-26-C-32 oxazole fragment 4 and its C-32 epimer 20 of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C is presented. The syn methyl arrangement in 4 was established through cyclic stereocontrol. Several methods for oxidizing the intermediate oxazolines 18 and 19 to the finished oxazole fragments were explored. The best results were obtained with oxidations proceeding through the corresponding ester enolate when the carbamate NH side chain was temporarily protected with a TMS group, or with CuBr2/DBU/HMTA-based oxidations. The finished oxazole fragment 4 was obtained in 21% overall yield, starting from Boc-D-alaninal.

  DOI：

  10.1021/jo971167m

文献信息

• Conformational analysis of (R,S)-4-amido-2,4-dimethyl-butyric acid derivatives
  作者：Reinhard W. Hoffmann、Miguel A. Lazaro、Francisco Caturla、Eric Framery、Ingrid Valancogne、Christian A.G.N. Montalbetti

  DOI：10.1016/s0040-4039(99)01226-5

  日期：1999.8

  NMR spectra of various N-acyl derivatives of (R,S)-4-amino-2,4-dimethyl-butyric acid show these compounds to be biconformational, populating the conformers 4 and 5 of the molecular backbone. Both predominant conformers have the amide group gauche to the main chain, (C) 1999 Elsevier Science Ltd. All rights reserved.
• Conformational analysis of 4-amido-2,4-dimethylbutyric acid derivatives
  作者：Reinhard W. Hoffmann、Francisco Caturla、Miguel A. Lazaro、Eric Framery、M. Carmen Bernabeu、Ingrid Valancogne、Christian A. G. N. Montalbetti

  DOI：10.1039/a910179i

  日期：——

  Both syn- and anti-4-amido-2,4-dimethylbutyric acid derivatives 5 and 6 were found to populate a conformation in which the amido group is gauche to the main chain of the molecule. In the anti series (6) a single conformation predominates, in which the acid carbonyl group is also gauche to the main chain. In the syn series (5) two local conformers prevail about the C-2–C-3 bond.

  研究发现，同系和反系 4-氨基-2,4-二甲基丁酸衍生物 5 和 6 都有一个氨基与分子主链同向的构象。在反系列（6）中，一种单一的构象占主导地位，其中的酸羰基也与主链呈高位。在同系列（5）中，C-2-C-3 键的两个局部构象占主导地位。
• Synthesis of the C₂₆−C₃₂ Oxazole Fragment of Calyculin C:  A Test Case for Oxazole Syntheses
  作者：Petri M. Pihko、Ari M. P. Koskinen

  DOI：10.1021/jo971167m

  日期：1998.1.1

  The synthesis of the C-26-C-32 oxazole fragment 4 and its C-32 epimer 20 of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C is presented. The syn methyl arrangement in 4 was established through cyclic stereocontrol. Several methods for oxidizing the intermediate oxazolines 18 and 19 to the finished oxazole fragments were explored. The best results were obtained with oxidations proceeding through the corresponding ester enolate when the carbamate NH side chain was temporarily protected with a TMS group, or with CuBr2/DBU/HMTA-based oxidations. The finished oxazole fragment 4 was obtained in 21% overall yield, starting from Boc-D-alaninal.