(E)-3-phenylprop-2-enyl N-hydroxycarbamate | 103723-92-8

• 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: (E)-3-phenylprop-2-enyl N-hydroxycarbamate
• 英文别名: [(E)-3-phenylprop-2-enyl] N-hydroxycarbamate
• CAS: 103723-92-8
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: VEWGAMWMLDCXFK-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (E)-3-phenylprop-2-enyl N-hydroxycarbamate 在 iron(II) tetrafluoroborate 、 （3aS，8aR）-2-（吡啶-2-基）-8,8a-二氢-3aH-茚并[1,2-d]恶唑 、 triethylamine tris(hydrogen fluoride) 、 N,N'-二环己基碳二亚胺 、 ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 生成 4-(fluoro(phenyl)methyl)oxazolidin-2-one
  参考文献：
  名称：

  铁（II）催化的分子内烯烃氨基氟化

  摘要：

  据报道，铁（II）催化的非对映选择性烯烃氨基氟化（dr高达> 20：1）。这一新的转变应用了功能化的羟胺和Et 3 N·3HF作为氮和氟源，这有助于从烯丙基醇衍生物高效合成β-氟伯胺和氨基酸。初步的机理研究表明，铁-类异戊二烯是一种可能的中间体，其反应性和对映选择性可以通过配体有效地调节。

  DOI：

  10.1021/ol501051p
• 作为产物：
  描述：

  cinnamyl chloroformate 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (E)-3-phenylprop-2-enyl N-hydroxycarbamate
  参考文献：
  名称：

  Kirby, Gordon W.; McGuigan, Henry; McLean, David, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1961 - 1966

  摘要：

  DOI：

文献信息

• Tethered Aminohydroxylation:  Dramatic Improvements to the Process
  作者：Timothy J. Donohoe、Carole J. R. Bataille、William Gattrell、Johannes Kloesges、Emilie Rossignol

  DOI：10.1021/ol070430v

  日期：2007.4.1

  [reaction: see text] Changing the identity of the N leaving group on a hydroxylamine-based reoxidant gives a dramatic improvement to the tethered aminohydroxylation reaction. Using OCOC6F5 as a leaving group means that only 1 mol % of osmium is required and yields as high as 98% can be obtained. Acyclic homoallylic alcohols were substrates considered too unreactive for effective use in the tethered

  [反应：见正文]改变基于羟胺的再氧化剂上的N离去基团的身份，可以大大改善束缚的氨基羟基化反应。使用OCOC6F5作为离去基团意味着仅需要1 mol％的and，并且可以获得高达98％的产率。无环均烯丙基醇被认为对于在束缚的氨基羟基化反应中不能有效使用而反应性太低。改善的反应条件意味着它们现已成为可行的氧化底物。
• Copper-Catalyzed Tethered Aziridination of Unsaturated <i>N-</i>Tosyloxy Carbamates
  作者：Renmao Liu、Steven R. Herron、Steven A. Fleming

  DOI：10.1021/jo0705014

  日期：2007.7.1

  nitrene addition to alkenes. The carbamate group was used as the tether between the alkene and the nitrene. Subsequent nucleophilic attack of the aziridine was accomplished using RSH, R2NH, N3-, or ROH as the nucleophile. This addition was found to be regio- and stereoselective. This methodology has been used to demonstrate its utility in the regio- and stereoselective synthesis of a 1,2-diamino-3-hydroxycyclohexane

  氮丙啶是通过铜催化的分子内氮烯加成烯烃而形成的。氨基甲酸酯基团被用作烯烃和腈之间的系链。氮丙啶的后续亲核攻击是使用RSH完成，R 2 NH，N 3 - ，或ROH作为亲核试剂。发现这种添加是区域和立体选择性的。该方法已用于证明其在1，2-二氨基-3-羟基环己烷的区域和立体选择性合成中的效用。这种替代模式存在于天然产品（例如达菲）中。
• Copper-Catalyzed Alkene Aziridination with <i>N</i>-Tosyloxycarbamates
  作者：Hélène Lebel、Sylvain Lectard、Michaël Parmentier

  DOI：10.1021/ol702152e

  日期：2007.11.1

  Pyridine copper complexes were found as active catalysts for the intramolecular aziridination of allylic N-tosyloxycarbamates and the intermolecular aziridination of styrenes with trichloroethyl N-tosyloxycarbamates. Free aziridines were easily obtained by basic deprotection of the trichloroethyl group.
• Iron(II)-Catalyzed Intramolecular Aminohydroxylation of Olefins with Functionalized Hydroxylamines
  作者：Guan-Sai Liu、Yong-Qiang Zhang、Yong-An Yuan、Hao Xu

  DOI：10.1021/ja311923z

  日期：2013.3.6

  A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral iron(II) complexes and preliminary mechanistic studies reveal an iron nitrenoid is a possible intermediate that can undergo either aminohydroxylation or aziridination, and the selectivity can be controlled by careful selection of counteranion/ligand combinations.
• Iron-Catalyzed Intra-intermolecular Aminoazidation of Alkenes
  作者：Sandra Abi Fayssal、Alessandro Giungi、Farouk Berhal、Guillaume Prestat

  DOI：10.1021/acs.oprd.9b00400

  日期：2020.5.15

  An intra-intermolecular iron-catalyzed aminoazidation of non-activated alkenes is reported for the preparation of imidazolidinone, oxazolidinone, and pyrrolidinone derivatives. The method uses cheap and abundant iron as a catalyst and commercially available TMSN3 as an azide source. This domino process allows, in a single operating step, for a ring-closure that generates an aza-heterocycle and the introduction of an azido appendage tethered to the heterocycle. The conditions developed offer a sustainable alternative method for the preparation of unsymmetrical vicinal diamine compounds.