(2S)-2-(cyclohexylamino)-3-phenylpropan-1-ol | 91373-83-0

• 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: (2S)-2-(cyclohexylamino)-3-phenylpropan-1-ol
• 英文别名: (S)-2-cyclohexylamino-3-phenylpropan-1-ol
• CAS: 91373-83-0
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: FKLSZTOLBXBGNY-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (2S)-2-(cyclohexylamino)-3-phenylpropan-1-ol 在 三乙胺 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 以85%的产率得到(R)-1-cyclohexylamino-3-phenylpropan-2-ol
  参考文献：
  名称：

  Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol

  摘要：

  N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, beta-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.072
• 作为产物：
  描述：

  L-苯丙氨醇 、 环己酮 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 、 水 为溶剂， 反应 12.0h， 以85%的产率得到(2S)-2-(cyclohexylamino)-3-phenylpropan-1-ol
  参考文献：
  名称：

  Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol

  摘要：

  N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, beta-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.072

文献信息

• Optically active N-substituted phenylalaninols and use therefor
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0105696A1

  公开（公告）日：1984-04-18

  Optically active N-substituted phenylalaninols of the formula (I): wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenryl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.

  式(I)的光学活性 N-取代的苯丙氨醇： 其中 R 为异丙基、1-乙基丙基、环戊基、环己基、环庚基、4-甲基苄基、4-甲氧基苄基或 3,4-亚甲二氧基苄基；及其可用作溶解剂的酸加成盐，以及制备 D-3-乙酰巯基-2-甲基丙酸的工艺，该工艺包括使 DL-3-乙酰巯基-2-甲基丙酸与光学活性 N-取代的式 (I) 苯丙氨醇反应，形成非对映异构盐、将形成的非对映异构盐从溶剂中进行分馏结晶，以分离 D 酸盐和 L 酸盐，然后用矿物酸分解 D 酸盐，得到 D-3-乙酰硫基-2-甲基丙酸。
• Resin inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0184855A2

  公开（公告）日：1986-06-18

  The invention relates to renin inhibiting compounds of the formula wherein A is an N-protecting group; R1, R3, R5 and R7 are loweralkyl or lipophilic or aromatic amino acid side chains and may be the same or different; R2, R4 and R6 are hydrogen or loweralkyl and may be the same or different; X is hydrogen, loweralkyl or -Ch20Ra, wherein R8 is hydrogen, loweralkyl or alkaryl; and R9 is loweralkyl, hydroxy, hydroxyalkyl, alkoxy, allyl, alkaryloxy or thioalkyl and pharmaceutically acceptable salts thereof.

  本发明涉及式中 A 为 N-保护基团的肾素抑制化合物；R1、R3、R5 和 R7 为低级烷基或亲油性或芳香族氨基酸侧链，可以相同或不同；R2、R4 和 R6 为氢或低级烷基，可以相同或不同；X 为氢、低级烷基或-Ch20Ra，其中 R8 为氢、低级烷基或芳基；R9 为低级烷基、羟基、羟烷基、烷氧基、烯丙基、烷芳氧基或硫代烷基及其药学上可接受的盐。
• Synthesis, reactivity and structural study of diastereomeric titanium complexes with amino acid derived N- and O-π donor ligands
  作者：Catherine K Ho、Aaron D Schuler、Christine B Yoo、Steven R Herron、Katherine A Kantardjieff、Adam R Johnson

  DOI：10.1016/s0020-1693(02)01180-5

  日期：2002.12

  Two diastereomeric Ti(IV) complexes of the type [Ti(Cl)(NMe2)(-OCH2CH(CH2Ph)N(R)-)](2) (where R = Pr-i or cyclo-C6H11) have been synthesized by protonolysis of TiCl(NMe2)(3) with the corresponding N-substituted amino alcohols. The chiral ligands were synthesized in a two-step procedure from L-phenylalanine ethyl ester. The complexes bridge through the amino alcohol oxygen atoms, and contain terminal chlorides. The remaining dimethylamide group can be replaced by a protonolysis reaction with 2,6-diisopropylphenol. The bulky disubstituted phenoxide ligand does not inhibit dimerization, and the amino alcohol oxygen bridged complex [Ti(Cl)(O-2,6-Pr-i(2)-C6H3)(OCH2CH(CH2Ph)NR)](2) is obtained. The dimeric nature of the complexes was established by Xray crystallography. (C) 2002 Elsevier Science B.V. All rights reserved.
• TSUKAMOTO, MASATOSI;SAVAYAMA, TADAXIRO
  作者：TSUKAMOTO, MASATOSI、SAVAYAMA, TADAXIRO

  DOI：——

  日期：——
• US4536601A
  申请人：——

  公开号：US4536601A

  公开（公告）日：1985-08-20