(2R,3E)-2-(tert-butyloxycarbonylamino)-4-phenyl-3-buten-1-ol | 133625-99-7

• 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-(tert-butyloxycarbonylamino)-4-phenyl-3-buten-1-ol
• 英文别名: (E,R)-2-t-butoxycarbonylamino-4-phenyl-3-butenol；(E)-(R)-N-Boc-2-amino-4-phenyl-3-butenol；tert-butyl N-[(E,2R)-1-hydroxy-4-phenylbut-3-en-2-yl]carbamate
• CAS: 133625-99-7
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: ZQOCCWDEZIXAJE-WTNCMQEWSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  436.5±45.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3E)-2-(tert-butyloxycarbonylamino)-4-phenyl-3-buten-1-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以91%的产率得到N-Boc-D-homophenylalaninol
  参考文献：
  名称：

  Synthetic Elaboration of the Side Chain of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine:  A New Regio- and Stereoselective Strategy to δ-Functionalized β-Amino Alcohols

  摘要：

  An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.

  DOI：

  10.1021/jo970619s
• 作为产物：
  描述：

  (E)-(R)-(+)-3-(2'-phenyl-1'-ethylenyl)-2-oxazolidinone 在 4-二甲氨基吡啶 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3E)-2-(tert-butyloxycarbonylamino)-4-phenyl-3-buten-1-ol
  参考文献：
  名称：

  从丝氨酸衍生的亲核丙氨醇合成子的研究

  摘要：

  亲核合成子 (S)-(+)-4-(2-oxazolidonyl)-methyltriphenylphoshinyl iodide 6，可从 l-丝氨酸中分五步获得（总产率为 52%），与醛反应生成良好至极好的烯烃产率 (74-89%)，并且在某些情况下，对新双键提供出色的立体控制。新形成的双键的几何形状受醛的性质和反应条件的影响。讨论了烯烃构型的趋势。应用这种方法可以轻松制备含有烯丙基氮双键的分子，包括恶唑烷酮和 β，γ-不饱和氨基醇。几种不饱和恶唑烷酮以高产率（75% 至 90%）转化为 β,γ-不饱和氨基醇。

  DOI：

  10.1021/ja9906249

文献信息

• Synthesis of chiral vinylglycines
  作者：Pierre L. Beaulieu、Jean Simon Duceppe、Carolyne Johnson

  DOI：10.1021/jo00013a023

  日期：1991.6

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.
• Regio- and stereoselective synthesis of 1,3-aminoalcohol derivatives from allylamine derivatives via internal sulfinyl group participation
  作者：Sadagopan Raghavan、A. Rajender、Suju C. Joseph、M.Abdul Rasheed、K. Ravi Kumar

  DOI：10.1016/j.tetasy.2003.11.036

  日期：2004.1

  The regio- and stereoselective preparation of 1,3-aminoalcohol derivatives from protected allylamines via intramolecular participation by the sulfinyl group is reported. A carbamate protecting group on nitrogen leads to products arising from nucleophilic participation by both the sulfinyl and carbamate groups, while protection as the sulfonamide affords the product arising from sulfinyl group participation alone. (C) 2003 Elsevier Ltd. All rights reserved.
• BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204
  作者：BEAULIEU, PIERRE L.、DUCEPPE, JEAN-SIMON、JOHNSON, CAROLYNE

  DOI：——

  日期：——
• 1,3-Oxazin-2-ones vs tetrahydrofurans by iodocyclisation of 2-alkoxycarbonylamino-3-alken-1-ols
  作者：Joan Miquel Jordá-Gregori、Maria Eugenia González-Rosende*、Patricia Cava-Montesinos、José Sepúlveda-Arques、Roberta Galeazzi、Mario Orena

  DOI：10.1016/s0957-4166(00)00323-2

  日期：2000.9

  Iodocyclisation of primary homoallylic alcohols 2a-d, containing either a 2-t-butoxy- or a benzyloxy-carbonylamino group, was studied, in order to establish the nucleophilic group involved in cyclofunctionalisation. In fact, the N-t-Boc derivative 2a gave the oxazinone 3, exclusively, whereas starting from the N-Cbz derivative 2b a diastereomeric mixture of substituted tetrahydrofurans 4 and 5 resulted in ratios depending upon the reaction conditions. These results were rationalised by means of computational methods. On the contrary, migration of both the t-butyl or benzyl group to the hydroxy group was observed when both 2c and 2d underwent cyclisation to give the corresponding 5-alkoxymethyl oxazolidin-2-ones 7a,b in low yield, but with high regio- and stereocontrol. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthetic Elaboration of the Side Chain of (<i>R</i>)-2,2-Dimethyl-3-(<i>tert</i>-butoxycarbonyl)-4-ethynyloxazolidine:  A New Regio- and Stereoselective Strategy to δ-Functionalized β-Amino Alcohols
  作者：Gianna Reginato、Alessandro Mordini、Massimo Caracciolo

  DOI：10.1021/jo970619s

  日期：1997.9.1

  An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.