(2R,3R)-3-amino-1-benzyloxypent-4-en-2-ol | 203397-91-5

• 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: (2R,3R)-3-amino-1-benzyloxypent-4-en-2-ol
• 英文别名: (2R,3R)-3-amino-1-phenylmethoxypent-4-en-2-ol
• CAS: 203397-91-5
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: SLTLXQNSUZJANH-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-amino-1-benzyloxypent-4-en-2-ol 在 4-二甲氨基吡啶 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 (4R,5R)-4-Benzyloxymethyl-2-methyl-5-vinyl-4,5-dihydro-oxazole
  参考文献：
  名称：

  A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

  摘要：

  Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

  DOI：

  10.1021/jo0262053
• 作为产物：
  描述：

  (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol 在 草酰氯 、 氨 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 反应 75.92h， 生成 (2R,3R)-3-amino-1-benzyloxypent-4-en-2-ol
  参考文献：
  名称：

  Lindstroem, Ulf M.; Somfai, Peter, Synthesis, 1998, # 1, p. 109 - 117

  摘要：

  DOI：

文献信息

• A stereospecific synthesis of vicinal amino alcohols by aminolysis of vinylepoxides
  作者：Ulf M. Lindström、Remi Franckowiak、Nathalie Pinault、Peter Somfai

  DOI：10.1016/s0040-4039(97)00224-4

  日期：1997.3

  Several vinylepoxides have been prepared and subjected to a TsOH·H2O-catalyzed aminolysis reaction to afford the corresponding amino alcohols in good yields. The nucleophilic addition is stereospecific and proceeds with high regioselectivity at the allylic position, unless other stereoelectronic effects competes. The aminolysis reaction is sensitive to steric hindrance at or in the proximity of the

  已经制备了几种乙烯基环氧化物，并使其经过TsOH·H 2 O催化的氨解反应，以高收率得到相应的氨基醇。亲核加成是立体特异性的，并且在烯丙基位置具有高区域选择性，除非其他立体电子效应竞争。氨解反应对环氧乙烷核或其附近的空间位阻敏感。
• A Highly Stereoselective Aza-[3,3]-Claisen Rearrangement of Vinylaziridines as a Novel Entry to Seven-Membered Lactams
  作者：Ulf M. Lindström、Peter Somfai

  DOI：10.1021/ja971572v

  日期：1997.9.1
• Microwave-assisted aminolysis of vinylepoxides
  作者：Ulf M. Lindström、Berit Olofsson、Peter Somfai

  DOI：10.1016/s0040-4039(99)01811-0

  日期：1999.12

  Di- and trisubstituted vinylepoxides in NH4OH were subjected to microwave irradiation affording the corresponding vicinal aminoalcohols in high yields. The reaction is stereospecific and highly regioselective for addition at the allylic carbon. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A Regio- and Stereodivergent Synthesis of <i>v</i><i>ic</i>-Amino Alcohols
  作者：Berit Olofsson、Uttam Khamrai、Peter Somfai

  DOI：10.1021/ol006736i

  日期：2000.12.1

  [GRAPHICS]A regio- and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by suitable nucleophiles and makes use of reactions that perform such tasks selectively with either retention or inversion of configuration.
• Determination of the relative configuration of vic-amino alcohols
  作者：Berit Olofsson、Peter Somfai

  DOI：10.1016/s0040-4039(02)02787-9

  日期：2003.2

  A large set of syn- and anti-1,2-amino alcohols has been synthesized. Upon comparison of the CHO and CHN H-1 NMR shifts a general trend has been observed, making it possible to determine the relative configuration of 1,2-amino alcohols without derivatization or shift reagents. (C) 2003 Elsevier Science Ltd. All rights reserved.