(S)-3-(benzoylamino)butanoic acid | 74720-06-2

• 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: (S)-3-(benzoylamino)butanoic acid
• 英文别名: (3S)-3-benzamidobutanoic acid
• CAS: 74720-06-2
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: UKRUGGNUDYQEGF-QMMMGPOBSA-N

物化性质

• 沸点：
  461.2±28.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzoylamino)butanoic acid 在 硫酸 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (S)-3-(benzoylamino)-4-pentene
  参考文献：
  名称：

  Stereospecific Synthesis of Oligonucleotides Containing Crotonaldehyde Adducts of Deoxyguanosine

  摘要：

  Crotonaldehyde reacts with DNA to form two diastereomeric 1,N-2 cyclic adducts of deoxyguanosine. A synthesis of the two diastereomeric deoxynucleosides has been achieved by reaction of mixed diastereomers of 4-amino-1,2-pentanediol with 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The resulting N-2-(1-methyl-3,4-dihydroxybutyl)-deoxyguanosine was treated with NaIO4, cleaving the vicinal diol to the aldehyde. Spontaneous cyclization gave the two diastereomers of the crotonaldehyde-adducted nucleoside that were readily separated by HPLC. The absolute configurations were assigned by an enantiospecific synthesis of one diastereomer from (S)-3-aminobutanoic acid. The synthetic strategy has been extended to preparation of a site-specifically adducted oligonucleotide by reaction of the mixed diastereomers of 4-amino-1,2-pentanediol with an 8-mer oligonucleotide containing 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The diastereomeric oligonucleotides were separated by HPLC and absolute configurations of the adducts were established by enzymatic digestion to the adducted nucleosides.

  DOI：

  10.1021/tx0100690
• 作为产物：
  描述：

  (S)-3-氨基丁酸 、 苯甲酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (S)-3-(benzoylamino)butanoic acid
  参考文献：
  名称：

  在2-位上的3-氨基丁酸非对映选择性烷基化†

  摘要：

  2位非对映选择性烷基化3-氨基丁酸

  DOI：

  10.1002/hlca.19880710724

文献信息

• Drey, Charles N. C.; Ridge, Richard J.; Mtetwa, Eli, Journal of the Chemical Society. Perkin transactions I, 1980, p. 378 - 380
  作者：Drey, Charles N. C.、Ridge, Richard J.、Mtetwa, Eli

  DOI：——

  日期：——
• Lewis acid-promoted 1,4-addition to chiral imide derivatives in the synthesis of .beta.-amino acids
  作者：Rosa Amoroso、Giuliana Cardillo、Piera Sabatino、Claudia Tomasini、Alessandra Trere

  DOI：10.1021/jo00073a017

  日期：1993.10

  The 1,4-addition of O-benzylhydroxylamine to imides 3 in the presence of various Lewis acids is described. The reaction is performed in CH2Cl2 at -78-degrees-C and affords derivatives 4 and 5 in good chemical yields and in different diastereomeric ratios, depending on the Lewis acid employed. TiCl4 and Me2AlCl give opposite diastereoselectivities. Furthermore, enantiomerically pure beta-amino acid 9 is obtained in good yield from compound 4a.
• Drey, Charles N. C.; Mtetwa, Eli, Journal of the Chemical Society. Perkin transactions I, 1982, # 7, p. 1587 - 1592
  作者：Drey, Charles N. C.、Mtetwa, Eli

  DOI：——

  日期：——