(2R)-2-(diallylamino)-2-phenylethanol | 860304-23-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2-(diallylamino)-2-phenylethanol
• 英文别名: (R)-2-N,N-diallylamino-2-phenylethanol；(R)-2-(diallylamino)-2-phenylethanol；(2R)-2-[bis(prop-2-enyl)amino]-2-phenylethanol
• CAS: 860304-23-0
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: KLHPISNIBVRGAX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-(diallylamino)-2-phenylethanol 在 sodium hydride 、 硫代水杨酸 、 1,4-双(二苯基膦)丁烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 24.17h， 生成 (R)-1-phenyl-2-(phenylmethoxy)ethylamine
  参考文献：
  名称：

  Functionalized Pyrrolidines Inhibit α-Mannosidase Activity and Growth of Human Glioblastoma and Melanoma Cells

  摘要：

  New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases were determined. (2.R,3R,4S)-2-({[(1R)-2-Hydroxy-1-phenylethyl]amino}methyl)pyrrolidine-3,4-diol ((+)-7a) was a potent and selective inhibitor of jack bean a-mannosidase (K-i = 135 nM). However, when evaluated on human tumor cells, 7a, and the reference compound swainsonine, did not efficiently inhibit the growth of glioblastoma cells. Further derivatization of the hydroxyl group with lipophilic groups to increase bioavailability improved their growth inhibitory properties for human glioblastoma and melanoma cells. In particular, the 4-bromobenzoyl derivative 26 demonstrated high efficacy for human tumor cells whereas primary human fibroblasts were less sensitive to 26. Therefore, functionalized pyrrolidines have the potential to inhibit the growth of tumor cells and display selectivity for tumor cells when compared to normal cells.

  DOI：

  10.1021/jm0409019
• 作为产物：
  描述：

  D-苯甘氨醇 、 3-溴丙烯 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以80%的产率得到(2R)-2-(diallylamino)-2-phenylethanol
  参考文献：
  名称：

  由β-氨基醇对映选择性合成β-氟胺：在LY503430合成中的应用

  摘要：

  N，N-二烷基-β-氨基醇通过使用N，N-二乙基氨基三氟化硫（DAST）进行对映体和区域选择性重排，从而以优异的收率和过量的对映体得到旋光性β-氟胺。该重排用于LY503430的对映选择性合成，LY503430是帕金森氏病的潜在治疗剂。

  DOI：

  10.1021/ol1019579

文献信息

• Highly Enantioselective Synthesis of β-Amino Alcohols
  作者：Thomas-Xavier Métro、Jérôme Appenzeller、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/ol061133d

  日期：2006.8.1

  [reaction: see text] N,N-Dialkyl-beta-amino alcohols derived from alpha-amino acids can be rearranged enantiospecifically by using TFAA/Et3N/NaOH to give 1,2-amino alcohols with enantiomeric excess up to 99%.

  [反应：见正文]通过使用TFAA / Et3N / NaOH，可以将源自α-氨基酸的N，N-二烷基-β-氨基醇进行对映体特异性重排，得到对映体过量最高达99％的1,2-氨基醇。
• Synthesis of enantiomerically pure (+)- and (−)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide
  作者：Isabelle Fernández、Luis Muñoz

  DOI：10.1016/j.tetasy.2006.08.006

  日期：2006.10

  The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of β-Fluoroamines from β-Amino Alcohols: Application to the Synthesis of LY503430
  作者：Béranger Duthion、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/ol1019579

  日期：2010.10.15

  N,N-Dialkyl-β-amino alcohols were enantiospecifically and regioselectively rearranged by using N,N-diethylaminosulfur trifluoride (DAST) to give optically active β-fluoroamines in excellent yields and enantiomeric excesses. This rearrangement was applied to the enantioselective synthesis of LY503430, a potential therapeutic agent for Parkinson’s disease.

  N，N-二烷基-β-氨基醇通过使用N，N-二乙基氨基三氟化硫（DAST）进行对映体和区域选择性重排，从而以优异的收率和过量的对映体得到旋光性β-氟胺。该重排用于LY503430的对映选择性合成，LY503430是帕金森氏病的潜在治疗剂。
• Functionalized Pyrrolidines Inhibit α-Mannosidase Activity and Growth of Human Glioblastoma and Melanoma Cells
  作者：Hélène Fiaux、Florence Popowycz、Sylvain Favre、Catherine Schütz、Pierre Vogel、Sandrine Gerber-Lemaire、Lucienne Juillerat-Jeanneret

  DOI：10.1021/jm0409019

  日期：2005.6.1

  New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases were determined. (2.R,3R,4S)-2-([(1R)-2-Hydroxy-1-phenylethyl]amino}methyl)pyrrolidine-3,4-diol ((+)-7a) was a potent and selective inhibitor of jack bean a-mannosidase (K-i = 135 nM). However, when evaluated on human tumor cells, 7a, and the reference compound swainsonine, did not efficiently inhibit the growth of glioblastoma cells. Further derivatization of the hydroxyl group with lipophilic groups to increase bioavailability improved their growth inhibitory properties for human glioblastoma and melanoma cells. In particular, the 4-bromobenzoyl derivative 26 demonstrated high efficacy for human tumor cells whereas primary human fibroblasts were less sensitive to 26. Therefore, functionalized pyrrolidines have the potential to inhibit the growth of tumor cells and display selectivity for tumor cells when compared to normal cells.