[(R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-oxo-3-thiophen-2-yl-propyl]-carbamic acid tert-butyl ester | 764715-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-oxo-3-thiophen-2-yl-propyl]-carbamic acid tert-butyl ester
• CAS: 764715-63-1
• 化学式: C₁₇H₂₅NO₅S
• 分子量: 355.455
• InChiKey: LOQPJOOJZGWSOI-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-oxo-3-thiophen-2-yl-propyl]-carbamic acid tert-butyl ester 在 盐酸 、 sodium periodate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 ((R)-1-Formyl-3-oxo-3-thiophen-2-yl-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis and preliminary evaluation of new d-3-heteroarylcarbonylalanines as ligands of the NMDA receptor

  摘要：

  New N-heteroarylcarbonylalanines of the D-series were stereoselectively prepared from enoates derived from D-mannitol. These compounds were active in binding and functional assays of the NMDA sub-type of glutamate receptors. A pyridine derivative inhibited MK801 binding, protected neurons from excitotoxic damage and blocked NMDA-induced currents in neurons. A thiophene derivative positively modulated the NMDA receptor, possibly through the allosteric glycine site. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.062
• 作为产物：
  描述：

  methyl (3R,4S)-3-butylamino-4,5-(isopropylidenedioxy)pentanoate 在 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 生成 [(R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-oxo-3-thiophen-2-yl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of β-amino arylketones through the addition of ArLi derivatives to β-aminoesters

  摘要：

  2-Lithiumthiophene and 2-lithiumpyridine were allowed to react with iv-substituted beta -aminoesters. Only beta -amino arylketones were obtained from N-BOC, IV-H derivatives, while arylenoates were formed (retro-conjugate addition) from those substrates bearing N-Bn, N-H substituents, despite the aryllithium used. When the nitrogen is disubstituted (BOC and Bn), the product distribution depended on the nucleophile, leading to tertiary alcohols for 2-lithiumthiophene or ketones for 2-lithiumpyridine. Tertiary alcohols were also formed when PhLi was used as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00358-6