(2R,R_S)-2-(tert-butylsulfinamido)pent-4-enoic acid | 1461641-94-0

• 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: (2R,R_S)-2-(tert-butylsulfinamido)pent-4-enoic acid
• 英文别名: (2R)-2-[[(R)-tert-butylsulfinyl]amino]pent-4-enoic acid
• CAS: 1461641-94-0
• 化学式: C₉H₁₇NO₃S
• 分子量: 219.305
• InChiKey: NQKPYKVWDVAYLF-NXSYQRQQSA-N

物化性质

• 沸点：
  373.4±52.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,R_S)-2-(tert-butylsulfinamido)pent-4-enoic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以69%的产率得到D-烯丙基甘氨酸
  参考文献：
  名称：

  Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: efficient synthesis of optically active γ,δ-unsaturated α-amino acids

  摘要：

  A convenient synthesis of delta,gamma-unsaturated amino acids has been developed. After a mixture of (R)-tert-butanesulfinamide and glyoxylic acid with molecular sieves in CH2Cl2 was stirred for 42 h at room temperature, allylboronic acid pinacol ester was added to the mixture to give (R)-2-((R)-tert-butanesulfinamido)pent-4-enoic acid with high diastereoselectivity. The corresponding reaction of (Z)-crotylboronic acid pinacol ester produced no product; however, that of (E)-crotylboronic acid pinacol ester produced (2R,3S)-2-((R)-tert-butylsulfinamido)-3-methylpent-4-enoic acid with excellent diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.026
• 作为产物：
  描述：

  烯丙基硼酸频哪醇酯 、 乙醛酸 、 (R)-(+)-叔丁基亚磺酰胺 以 二氯甲烷 、 水 为溶剂， 反应 65.0h， 以88%的产率得到(2R,R_S)-2-(tert-butylsulfinamido)pent-4-enoic acid
  参考文献：
  名称：

  Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: efficient synthesis of optically active γ,δ-unsaturated α-amino acids

  摘要：

  A convenient synthesis of delta,gamma-unsaturated amino acids has been developed. After a mixture of (R)-tert-butanesulfinamide and glyoxylic acid with molecular sieves in CH2Cl2 was stirred for 42 h at room temperature, allylboronic acid pinacol ester was added to the mixture to give (R)-2-((R)-tert-butanesulfinamido)pent-4-enoic acid with high diastereoselectivity. The corresponding reaction of (Z)-crotylboronic acid pinacol ester produced no product; however, that of (E)-crotylboronic acid pinacol ester produced (2R,3S)-2-((R)-tert-butylsulfinamido)-3-methylpent-4-enoic acid with excellent diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.026

文献信息

• Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: efficient synthesis of optically active γ,δ-unsaturated α-amino acids
  作者：Shigeo Sugiyama、Saori Imai、Keitaro Ishii

  DOI：10.1016/j.tetasy.2013.07.026

  日期：2013.9

  A convenient synthesis of delta,gamma-unsaturated amino acids has been developed. After a mixture of (R)-tert-butanesulfinamide and glyoxylic acid with molecular sieves in CH2Cl2 was stirred for 42 h at room temperature, allylboronic acid pinacol ester was added to the mixture to give (R)-2-((R)-tert-butanesulfinamido)pent-4-enoic acid with high diastereoselectivity. The corresponding reaction of (Z)-crotylboronic acid pinacol ester produced no product; however, that of (E)-crotylboronic acid pinacol ester produced (2R,3S)-2-((R)-tert-butylsulfinamido)-3-methylpent-4-enoic acid with excellent diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.