methyl (2S)-2-[(2-bromophenyl)methylamino]-3-phenylpropanoate | 1027501-59-2

• 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: methyl (2S)-2-[(2-bromophenyl)methylamino]-3-phenylpropanoate
• CAS: 1027501-59-2
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: KRYUJWKAULAHRN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(2-bromophenyl)methylamino]-3-phenylpropanoate 在 N-甲基吗啉 、 盐酸 、 n-butyl tin hydride 、 偶氮二异丁腈 、 sodium cyanoborohydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 3.5h， 生成 (3,4-dibenzyl-2-oxo-6-trimethylsilanylmethylene-[1,4]diazepan-1-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

  摘要：

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.

  DOI：

  10.1021/jo020602w
• 作为产物：
  描述：

  methyl (2S)-2-[(2-bromophenyl)methylideneamino]-3-phenylpropanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 methyl (2S)-2-[(2-bromophenyl)methylamino]-3-phenylpropanoate
  参考文献：
  名称：

  Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

  摘要：

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.

  DOI：

  10.1021/jo020602w

文献信息

• Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams
  作者：Robert Andrukiewicz、Rafał Loska、Vladimir Prisyahnyuk、Krzysztof Staliński

  DOI：10.1021/jo020602w

  日期：2003.2.1

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.