(S)-3-[4-(2,6-Dichloro-benzyloxy)-phenyl]-2-(4-methoxy-benzylamino)-propionic acid methyl ester | 610314-16-4

• 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-[4-(2,6-Dichloro-benzyloxy)-phenyl]-2-(4-methoxy-benzylamino)-propionic acid methyl ester
• CAS: 610314-16-4
• 化学式: C₂₅H₂₅Cl₂NO₄
• 分子量: 474.384
• InChiKey: BQNISDYLVJKIEA-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-3-[4-(2,6-Dichloro-benzyloxy)-phenyl]-2-(4-methoxy-benzylamino)-propionic acid methyl ester 在 三氯乙腈 、 三苯基膦 、 (叔丁基亚氨基)三(吡咯烷)膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 (3S,4S)-4-p-(2,6-dichlorobenzyloxy)benzyl-1-p-methoxybenzyl-4-methoxycarbonyl-3-methyl-2-azetidinone
  参考文献：
  名称：

  Optically active 1,3,4,4-tetrasubstituted β-lactams: Synthesis and evaluation as tumor cell growth inhibitors

  摘要：

  The in vitro cytotoxicity assays of several enantiopure (3S,4S)- and (3R,4R)-1,3,4,4-tetrasubstituted beta-lactams derived from amino acids have shown that the (3S,4S)-4-benzyl-1-p-methoxybenzyl-3-methyl-4-methoxycarbonyl derivative 2a, obtained from Phe, displays significant activity, which is comparable to that of the anticancer drug Doxorubicin against HT29 cell lines. Modifications at positions 1 and 4 of the beta-lactam ring led to identify the Tyr(2,6-ClBz) analogu 26d with similar activity data to those of 2a. The synthesis and SAR of all these tetrasubstituted beta-lactams are reported here. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.025
• 作为产物：
  描述：

  (S)-3-[4-(2,6-Dichloro-benzyloxy)-phenyl]-2-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-propionic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (S)-3-[4-(2,6-Dichloro-benzyloxy)-phenyl]-2-(4-methoxy-benzylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Memory of chirality in the stereoselective synthesis of β-lactams: importance of the starting amino acid derivative

  摘要：

  The enantioselectivity of the base-promoted cyclization of N-alkyl-N-chloroacetyl amino acid derivatives to beta-lactams is dependent on the substituents on the starting material. While Bu-t esters are preferred over Me esters, and N-Bzl-, N-Pmb, N-Nph and N-Mom groups gave similar e.e. values, only amino acid derivatives with branched side-chains at the gamma-position were able to show a good memory of chirality. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00398-7