(R)-2-(benzofuran-2-yl)-2-((R)-1,1-dimethylethylsulfinamido)acetic acid | 1370009-88-3

• 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: (R)-2-(benzofuran-2-yl)-2-((R)-1,1-dimethylethylsulfinamido)acetic acid
• 英文别名: (2R)-2-(1-benzofuran-2-yl)-2-[[(R)-tert-butylsulfinyl]amino]acetic acid
• CAS: 1370009-88-3
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: ISVJCQDKYKPRGQ-MPBGBICISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯并呋喃-2-硼酸 、 乙醛酸水合物 、 (R)-(+)-叔丁基亚磺酰胺 在 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到(R)-2-(benzofuran-2-yl)-2-((R)-1,1-dimethylethylsulfinamido)acetic acid
  参考文献：
  名称：

  Lewis Acid Promoted Highly Diastereoselective Petasis Borono-Mannich Reaction: Efficient Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids

  摘要：

  An efficient and straightforward method for the preparation of highly enantiomerically enriched beta,gamma-unsaturated a-amino acid derivatives by a Lewis acid promoted diastereoselective Petasis reaction of vinylboronic acid, N-tert-butanesulfinamide, and glyoxylic acid has been developed. The synthetic utilities of the approach were demonstrated by the rapid and convenient construction of challenging cyclopenta[o]proline derivatives.

  DOI：

  10.1021/ol300581n

文献信息

• Lewis Acid Promoted Highly Diastereoselective Petasis Borono-Mannich Reaction: Efficient Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids
  作者：Yi Li、Ming-Hua Xu

  DOI：10.1021/ol300581n

  日期：2012.4.20

  An efficient and straightforward method for the preparation of highly enantiomerically enriched beta,gamma-unsaturated a-amino acid derivatives by a Lewis acid promoted diastereoselective Petasis reaction of vinylboronic acid, N-tert-butanesulfinamide, and glyoxylic acid has been developed. The synthetic utilities of the approach were demonstrated by the rapid and convenient construction of challenging cyclopenta[o]proline derivatives.