(2R,3E)-2-amino-4-phenylbut-3-en-1-ol | 505085-76-7

• 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: (2R,3E)-2-amino-4-phenylbut-3-en-1-ol
• 英文别名: (E)-2-amino-4-phenylbut-3-en-1-ol；(2R)-2-Amino-4-phenylbut-3-en-1-ol；(E,2R)-2-amino-4-phenylbut-3-en-1-ol
• CAS: 505085-76-7
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: CKKVPCLNGXGAFO-VQCYPWCPSA-N

物化性质

• 沸点：
  336.9±42.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3E)-2-amino-4-phenylbut-3-en-1-ol 在 palladium on activated charcoal 氢气 、 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (5R,8aR)-5-phenylethyloxazolidino[3,4-a]piperidin-3-one
  参考文献：
  名称：

  Efficient access to chiral trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines via allylation of chiral imines and ring-closing metathesis

  摘要：

  Enantiomerically pure trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines are synthesized in five steps from Garner's aldehyde in 37-44% overall yield. This strategy is based on the allylation of chiral iminoalcohols formed in situ followed by a ring-closing metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02586-8
• 作为产物：
  描述：

  三苯基苄基溴化膦 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 为溶剂， 反应 5.5h， 生成 (2R,3E)-2-amino-4-phenylbut-3-en-1-ol
  参考文献：
  名称：

  使用不对称二羟基化技术快速有效地合成植物鞘氨醇

  摘要：

  描述了通过使用衍生自1-丝氨酸的旋光性烯烃的不对称二羟基化来简短合成植物鞘氨醇衍生物及其立体异构体。

  DOI：

  10.1016/s0040-4020(98)00615-2

文献信息

• A Novel Route to Chiraltrans-6-Alkyl-2-hydroxymethyl-1,2,5,6-tetrahydropyridines by Allylation of Chiral Imines and Ring-Closing Metathesis− Total Synthesis of (−)-3-epi-Deoxoprosopinine
  作者：François-Xavier Felpin、Kamal Boubekeur、Jacques Lebreton

  DOI：10.1002/ejoc.200300423

  日期：2003.12

  A novel route to enantiomerically pure trans-6-alkyl-2-hydroxymethyl-1,2,5,6-tetrahydropyridines is reported in five steps from Garner’s aldehyde with overall yields higher than 35 %. This strategy is based on the allylation of chiral imino alcohols formed in situ followed by a ring-closing metathesis. This new method was used for the first total synthesis of (−)-3-epi-deoxoprosopinine. (© Wiley-VCH

  报道了一种从 Garner 醛中分五个步骤制备对映体纯反式-6-烷基-2-羟甲基-1,2,5,6-四氢吡啶的新途径，总产率高于 35%。该策略基于原位形成的手性亚氨基醇的烯丙基化，然后是闭环复分解。这种新方法用于 (-)-3-epi-deoxoprosopinine 的首次全合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• A short and efficient synthesis of phytosphingosines using asymmetric dihydroxylation
  作者：Ritsuo Imashiro、Osamu Sakurai、Toyoharu Yamashita、Hiroshi Horikawa

  DOI：10.1016/s0040-4020(98)00615-2

  日期：1998.9

  A short synthesis of the phytosphingosine derivatives and their stereoisomers by using asymmetric dihydroxylation of the optically active olefins derived from l-serine is described.

  描述了通过使用衍生自1-丝氨酸的旋光性烯烃的不对称二羟基化来简短合成植物鞘氨醇衍生物及其立体异构体。
• The synthesis of chiral β-aryl-α,β-unsaturated amino alcohols via a Pd-catalyzed asymmetric allylic amination
  作者：Mao Quan、Nicholas Butt、Jiefeng Shen、Kaiji Shen、Delong Liu、Wanbin Zhang

  DOI：10.1039/c3ob41642a

  日期：——

  Chiral β-aryl-α,β-unsaturated amino alcohols were synthesized via a Pd-catalyzed asymmetric allylic amination of 4-aryl-1,3-dioxolan-2-one using planar chiral 1,2-disubstituted ferrocene-based phosphinooxazolines as ligands. Under the optimized reaction conditions, a series of substrates were examined and the products were obtained in good to excellent yields (up to 92%) and enantioselectivities (up to 98% ee) under mild reaction conditions. The desired products were determined to be of (R)-configuration and could subsequently be transformed into compounds with interesting biological activity using simple transformations.

  以平面手性 1,2-二取代二茂铁基膦恶唑为配体，通过钯催化 4-芳基-1,3-二氧戊环-2-酮的不对称烯丙基胺化反应合成了手性 δ-芳基-δ,δ-不饱和氨基醇。在优化的反应条件下，对一系列底物进行了研究，并在温和的反应条件下获得了良好至极佳的产率（高达 92%）和对映选择性（高达 98%ee）的产物。所需的产物被确定为 (R) 构型，随后可通过简单的转化过程转化为具有有趣生物活性的化合物。
• Efficient access to chiral trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines via allylation of chiral imines and ring-closing metathesis
  作者：François-Xavier Felpin、Jacques Lebreton

  DOI：10.1016/s0040-4039(02)02586-8

  日期：2003.1

  Enantiomerically pure trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines are synthesized in five steps from Garner's aldehyde in 37-44% overall yield. This strategy is based on the allylation of chiral iminoalcohols formed in situ followed by a ring-closing metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.