(1S,2R)-(-)-2-(N,N-diethylamino)-1-phenylpropan-1-ol | 37025-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-(-)-2-(N,N-diethylamino)-1-phenylpropan-1-ol
• 英文别名: (1S,2R)-2-(diethylamino)-1-phenylpropan-1-ol；(1S,2R)-1-Phenyl-2-(diethylamino)-1-propanol
• CAS: 37025-58-4
• 化学式: C₁₃H₂₁NO
• 分子量: 207.316
• InChiKey: JMFCQRKXGIHOAN-DGCLKSJQSA-N

物化性质

• 沸点：
  311.4±30.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  左旋去甲麻黄碱 、 碘乙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 (1S,2R)-(-)-2-(N,N-diethylamino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  手性complex络合物催化的直接不对称醛醇-季申科反应：抗1,3-二醇的合成。

  摘要：

  已开发出芳族醛与脂族和芳族酮的不对称aldol-Tishchenko反应，这是一种高效合成抗-1,3-二醇的有效策略，具有高非对映异构控制性和良好的对映选择性。这种多米诺型反应是由手性complex配合物催化的，该手性配合物通过羰基化合物的烯醇化和醛醇中间体的埃文斯-季申科还原而促进醛醇反应。还对所得二醇的立体化学进行了研究，并最终通过使用CD技术进行了证明。

  DOI：

  10.1002/chem.200600357

文献信息

• Chiral N,N-dialkylnorephedrines as catalysts of the highly enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes. The asymmetric synthesis of secondary aliphatic and aromatic alcohols of high optical purity
  作者：Kenso Soai、Shuji Yokoyama、Tomoiki Hayasaka

  DOI：10.1021/jo00013a035

  日期：1991.6

  The chiral N,N-dialkylnorephedrine-catalyzed addition of dialkylzincs to aliphatic and aromatic aldehydes afforded secondary alcohols of high optical purity (to > 95% ee). Among the N,N-di(primary alkyl)norephedrines, N,N-di-n-butylnorephedrine (DBNE, 3d) was found to be the most effective catalyst. 1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol (3i) and N,N-diallylnorephedrine (3j) were also highly effective catalysts. The method described provides optically active secondary aliphatic alcohols of high optical purity which cannot be prepared by conventional methods.
• Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters
  作者：Han Yu、Richard B Rothman、Christina M Dersch、John S Partilla、Kenner C Rice

  DOI：10.1016/s0968-0896(00)00210-8

  日期：2000.12

  Three metabolites of diethylpropion (1), (+/-)-2-ethylamino-1-phenyl-propan-1-one (2), (1 R,2S)-(-)-N,N-diethylnorephedrine (3a) and (1S,2R)-(-)-N,N-diethylnorephedrine (3b) were synthesized. Their uptake and release effects with biogenic amine transporters were evaluated. A major finding of this study is that the in vivo activity of diethylpropion on biogenic amine transporters is most likely due to metabolite 2 as diethylpropion (1) and the metabolites 3a and 3b showed little or no effect in the assays studied. These studies also revealed that 2 acted as a substrate at the norepinephrine (IC50=99nM) and serotonin transporters (IC50 = 2118 nM) and an uptake inhibitor at the dopamine transporter (IC50 = 1014 nM). The potent action of 2 at the NE transporter supports the hypothesis that amphetamine-type subjective effects may be mediated in part by brain norepinephrine. (C) 2000 Published by Elsevier Science Ltd.
• SOAI, KENSO;YOKOYAMA, SHUJI;HAYASAKA, TOMOIKI, J. ORG. CHEM., 56,(1991) N3, C. 4264-4268
  作者：SOAI, KENSO、YOKOYAMA, SHUJI、HAYASAKA, TOMOIKI

  DOI：——

  日期：——
• Chiral Ytterbium Complex-Catalyzed Direct Asymmetric Aldol-Tishchenko Reaction: Synthesis ofanti-1,3-Diols
  作者：Jacek Mlynarski、Bartosz Rakiel、Maciej Stodulski、Agata Suszczyńska、Jadwiga Frelek

  DOI：10.1002/chem.200600357

  日期：2006.10.25

  The asymmetric aldol-Tishchenko reaction of aromatic aldehydes with aliphatic and aromatic ketones has been developed as an efficient strategy for the synthesis of anti-1,3-diols in good yield with high diastereocontrol and good levels of enantioselectivity. This domino-type reaction is catalyzed by a chiral ytterbium complex that promotes both the aldol reaction through enolization of the carbonyl

  已开发出芳族醛与脂族和芳族酮的不对称aldol-Tishchenko反应，这是一种高效合成抗-1,3-二醇的有效策略，具有高非对映异构控制性和良好的对映选择性。这种多米诺型反应是由手性complex配合物催化的，该手性配合物通过羰基化合物的烯醇化和醛醇中间体的埃文斯-季申科还原而促进醛醇反应。还对所得二醇的立体化学进行了研究，并最终通过使用CD技术进行了证明。