(1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol | 154170-05-5

• 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: (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol
• 英文别名: (1R,2S)-1-phenyl-2-[[(1R)-1-phenylethyl]amino]propan-1-ol
• CAS: 154170-05-5
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: LBOCLSZSAJPKQA-KEYYUXOJSA-N

物化性质

• 沸点：
  385.2±12.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol 在 palladium 10% on activated carbon 氢气 作用下， 以 四氢呋喃 为溶剂， 35.0 ℃ 、303.99 kPa 条件下， 反应 144.0h， 以75%的产率得到去甲麻黄碱
  参考文献：
  名称：

  EP1512677

  摘要：

  公开号：
• 作为产物：
  描述：

  (R)-1-羟基-1-苯基丙酮 在 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 异丙醇 、 甲苯 为溶剂， 110.0 ℃ 、344.75 kPa 条件下， 生成 (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol
  参考文献：
  名称：

  Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines

  摘要：

  Enantiomerically pure N-alkylated beta-amino alcohols 1a, 1a', 1c, 1c', 1d, 1d', 1e and 1e', with ee 100% have been synthesized from phenylpropanolamines 2. Effect of the neighboring chiral environment on the newly formed chiral center has been studied experimentally and concluded that the newly formed chiral center's absolute configuration is opposite to the adjacent (alpha- or beta-) chiral environment. The antimicrobial activity of the synthesized beta-amino alcohols were screened using in vitro disc diffusion method and variable antimicrobial activities were shown for 1a, 1a', 1c, 1c', 1d, 1d', 1e & 1e' and amongst them 1d & 1d' exhibited significant activity against bacteria and fungi. In silico studies revealed all the synthesized beta-amino alcohols 1a-e and 1a'-e' have shown good binding energies ranging from -7.38 to -6.09 kJ/mol towards the target receptor DNA topoisomerase IV and 1d' has shown maximum binding energy -7.38 kJ/mol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.027

文献信息

• Efficient Synthesis of <i>Ephedra</i> Alkaloid Analogues Using an Enantiomerically Pure <i>N</i>-[(<i>R</i>)-(+)-α-Methylbenzyl]aziridine-2-carboxaldehyde
  作者：Gwon-Il Hwang、Jae-Ho Chung、Won Koo Lee

  DOI：10.1021/jo9603183

  日期：1996.1.1

  Efficient preparation of enantiomerically pure (2S)-aziridine-2-carboxaldehyde 9 and its 2(R) isomer and highly diastereoselective addition of organolithium reagents to the aldehyde 9 are described. The diastereoselectivity in additions of the lithium reagents seems to come from "chelation-controlled" carbon-carbon bond formation and is influenced by the source of the organometallic compound, solvent

  描述了对映体纯的（2S）-氮丙啶-2-甲醛9及其2（R）异构体的高效制备以及向醛9中高度非对映选择性地添加有机锂试剂。锂试剂中的非对映选择性似乎来自“螯合控制的”碳-碳键的形成，并受有机金属化合物的来源，溶剂和锂盐的存在的影响。加成产物的氮丙啶环的C（3）-N键在Pearlman催化剂的存在下通过催化氢化而区域选择性地还原，从而提供对映体纯的1,2-氨基醇。与市售的正伪麻黄碱相比，当C-1取代基为苯基时，将氨基醇13a的绝对立体化学指定为（1S，2S）。
• An efficient synthesis of both enantiomers of Cathinone by regioselective reductive ring opening of substituted aziridines
  作者：Gweon Il Hwang、Jae-Ho Chung、Won Koo Lee

  DOI：10.1016/0040-4020(96)00702-8

  日期：1996.9

  Both enantiomers of Cathinone were prepared as HCl salts from N-(R)-α-methylbenzylaziridine-2(S)-carboxaldehyde2c and its enantiomer N-(S)-α-methylbenzylaziridine-2(R)-carboxaldehyde3c in high yield. This process makes it possible to prepare other aromatic and heteroaromatic analogs of Cathinone efficiently.

  卡西酮的两种对映体制备为从盐酸盐ñ - （[R ）- α -methylbenzylaziridine -2（小号）-1-甲醛2C及其对映体ñ - （小号） - α -methylbenzylaziridine-2（[R）-1-甲醛3c中以高收率。该方法使得可以有效地制备卡西酮的其他芳族和杂芳族类似物。
• Process for producing optically active beta-amino alcohol
  申请人：Nishiyama Akira

  公开号：US20050277791A1

  公开（公告）日：2005-12-15

  A process for easily producing an optically active β-amino alcohol useful as a pharmaceutical intermediate from an inexpensive, readily available starting material is provided. A readily available α-substituted ketone is reacted with an optically active amine to yield a diastereomer mixture of an optically active α-substituted aminoketone. One of the diastereomers is isolated optionally after the diastereomers are converted to salts with an acid. The optically active α-substituted aminoketone or a salt thereof thus isolated was stereoselectively reduced to yield an optically active β-substituted amino alcohol. The optically active β-substituted amino alcohol is subjected to hydrogenolysis to produce an optically active β-amino alcohol or a salt thereof.

  提供了一种从廉价、易得的起始材料中轻松生产有用于制药中间体的光学活性β-氨基醇的方法。将易得的α-取代酮与光学活性胺反应，得到光学活性α-取代氨基酮的对映体混合物。在对映体混合物与酸转化为盐之后，可以选择性地分离其中一种对映体。分离出的光学活性α-取代氨基酮或其盐经立体选择性还原，得到光学活性β-取代氨基醇。将光学活性β-取代氨基醇进行氢解反应，得到光学活性β-氨基醇或其盐。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE s-AMINO ALCOHOL
  申请人：KANEKA CORPORATION

  公开号：EP1512677A1

  公开（公告）日：2005-03-09

  A process for easily producing an optically active β-amino alcohol useful as a pharmaceutical intermediate from an inexpensive, readily available starting material is provided. A readily available α-substituted ketone is reacted with an optically active amine to yield a diastereomer mixture of an optically active α-substituted aminoketone. One of the diastereomers is isolated optionally after the diastereomers are converted to salts with an acid. The optically active α-substituted aminoketone or a salt thereof thus isolated was stereoselectively reduced to yield an optically active β-substituted amino alcohol. The optically active β-substituted amino alcohol is subjected to hydrogenolysis to produce an optically active β-amino alcohol or a salt thereof.

  本发明提供了一种利用廉价易得的起始原料轻松生产具有光学活性的 β-氨基醇作为药物中间体的工艺。现成的 α 取代酮与光学活性胺反应，生成光学活性 α 取代氨基酮的非对映异构体混合物。非对映异构体中的一种非对映异构体在与酸转化成盐后被分离出来。这样分离出的具有光学活性的 α-取代氨基酮或其盐经立体选择性还原后得到具有光学活性的 β-取代氨基醇。将光学活性 β-取代氨基醇进行氢解，生成光学活性 β-氨基醇或其盐。
• US7408084B2
  申请人：——

  公开号：US7408084B2

  公开（公告）日：2008-08-05