(R)-benzyl 2-(dibenzylamino)-propanoate | 668436-83-7

• 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)-benzyl 2-(dibenzylamino)-propanoate
• 英文别名: benzyl (2R)-2-(dibenzylamino)propanoate
• CAS: 668436-83-7
• 化学式: C₂₄H₂₅NO₂
• 分子量: 359.468
• InChiKey: MNOBWYXQIILDKX-HXUWFJFHSA-N

物化性质

• 沸点：
  469.4±33.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-benzyl 2-(dibenzylamino)-propanoate 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (Z,2R,3S)-2-(dibenzylamino)dodec-8-en-3-ol
  参考文献：
  名称：

  Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols

  摘要：

  An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.010
• 作为产物：
  描述：

  D-丙氨酸 、 氯化苄 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以89%的产率得到(R)-benzyl 2-(dibenzylamino)-propanoate
  参考文献：
  名称：

  Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols

  摘要：

  An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.010

文献信息

• Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds
  作者：Gilles Berger、Michel Gelbcke、Emilie Cauët、Michel Luhmer、Jean Nève、François Dufrasne

  DOI：10.1016/j.tetlet.2012.11.079

  日期：2013.2

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.