2-bromopropanoic-2-d acid-d | 1239453-22-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-bromopropanoic-2-d acid-d
• CAS: 1239453-22-5
• 化学式: C₃H₅BrO₂
• 分子量: 154.96
• InChiKey: MONMFXREYOKQTI-YQWZEFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-乳酸苄酯 、 2-bromopropanoic-2-d acid-d 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 DPTS 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以89%的产率得到(S)-1-(benzyloxy)-1-oxopropan-2-yl 2-bromopropanoate-2-d
  参考文献：
  名称：

  New Insights into Poly(lactic-co-glycolic acid) Microstructure: Using Repeating Sequence Copolymers To Decipher Complex NMR and Thermal Behavior

  摘要：

  Sequence, which Nature uses to spectacular advantage, has not been fully exploited in synthetic copolymers. To investigate the effect of sequence and stereosequence on the physical properties of copolymers, a family of complex isotactic, syndiotactic, and atactic repeating sequence poly(lactic-co-glycolic acid) copolymers (RSC PLGAs) were prepared and their NMR and thermal behavior was studied. The unique suitability of polymers prepared from the bioassimilable lactic and glycolic acid monomers for biomedical applications makes them ideal candidates for this type of sequence engineering. Polymers with repeating units of LG, GLG and LLG (L = lactic, G = glycolic) with controlled and varied tacticities were synthesized by assembly of sequence-specific, stereopure dimeric, trimeric, and hexameric segmer units. Specifically labeled deuterated lactic and glycolic acid segmers were likewise prepared and polymerized. Molecular weights for the copolymers were in the range M-n = 12-40 kDa by size exclusion chromatography in THF. Although the effects of sequence-influenced solution conformation were visible in all resonances of the H-1 and C-13 NMR spectra, the diastereotopic methylene resonances in the H-1 NMR (CDCl3) for the glycolic units of the copolymers proved most sensitive. An octad level of resolution, which corresponds to an astounding 31-atom distance between the most separated stereocenters, was observed in some mixed sequence polymers. Importantly, the level of sensitivity of a particular NMR resonance to small differences in sequence was found to depend on the sequence itself. Thermal properties were also correlated with sequence.

  DOI：

  10.1021/ja102670n
• 作为产物：
  描述：

  反应 1.0h， 以25.9 g的产率得到2-bromopropanoic-2-d acid-d
  参考文献：
  名称：

  New Insights into Poly(lactic-co-glycolic acid) Microstructure: Using Repeating Sequence Copolymers To Decipher Complex NMR and Thermal Behavior

  摘要：

  Sequence, which Nature uses to spectacular advantage, has not been fully exploited in synthetic copolymers. To investigate the effect of sequence and stereosequence on the physical properties of copolymers, a family of complex isotactic, syndiotactic, and atactic repeating sequence poly(lactic-co-glycolic acid) copolymers (RSC PLGAs) were prepared and their NMR and thermal behavior was studied. The unique suitability of polymers prepared from the bioassimilable lactic and glycolic acid monomers for biomedical applications makes them ideal candidates for this type of sequence engineering. Polymers with repeating units of LG, GLG and LLG (L = lactic, G = glycolic) with controlled and varied tacticities were synthesized by assembly of sequence-specific, stereopure dimeric, trimeric, and hexameric segmer units. Specifically labeled deuterated lactic and glycolic acid segmers were likewise prepared and polymerized. Molecular weights for the copolymers were in the range M-n = 12-40 kDa by size exclusion chromatography in THF. Although the effects of sequence-influenced solution conformation were visible in all resonances of the H-1 and C-13 NMR spectra, the diastereotopic methylene resonances in the H-1 NMR (CDCl3) for the glycolic units of the copolymers proved most sensitive. An octad level of resolution, which corresponds to an astounding 31-atom distance between the most separated stereocenters, was observed in some mixed sequence polymers. Importantly, the level of sensitivity of a particular NMR resonance to small differences in sequence was found to depend on the sequence itself. Thermal properties were also correlated with sequence.

  DOI：

  10.1021/ja102670n