O-(1-phenyl-but-3-enyl)-N-(tert-butyloxycarbonyl)hydroxylamine | 484068-27-1

• 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: O-(1-phenyl-but-3-enyl)-N-(tert-butyloxycarbonyl)hydroxylamine
• 英文别名: (+/-)-tert-butyl (1-phenylbut-3-en-1-yl)oxycarbamate；N-[(1-phenylbut-3-enyl)oxy]-tert-butoxycarbamate；(+/-)-tert-butyl 1-phenylbut-3-enyloxycarbamate；tert-butyl N-(1-phenylbut-3-enoxy)carbamate
• CAS: 484068-27-1
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: TXUPVTOVDCZTGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-(1-phenyl-but-3-enyl)-N-(tert-butyloxycarbonyl)hydroxylamine 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 氯仿 、 potassium tert-butylate 作用下， 反应 24.0h， 以24%的产率得到
  参考文献：
  名称：

  Synthesis of Isoxazolidines by Intramolecular Hydroamination of N-Alkoxyamides in the Presence of a Visible-Light Photoredox Catalyst

  摘要：

  在钌光催化剂的作用下，通过对 N-烷氧基酰胺进行分子内氢化反应，以中等至良好的产率获得了 N-酰基异噁唑烷。在该反应中，通过去质子化生成的 N-烷氧基酰胺阴离子经过光催化单电子转移（SET）氧化生成相应的自由基，自由基环化生成异噁唑烷环。值得注意的是，这种方法适用于大环底物，可得到相应的含 12 个大环的产物。

  DOI：

  10.1246/bcsj.20190127
• 作为产物：
  描述：

  1-苯基-3-丁烯-1-醇 在 一水合肼 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 27.03h， 生成 O-(1-phenyl-but-3-enyl)-N-(tert-butyloxycarbonyl)hydroxylamine
  参考文献：
  名称：

  立体选择钯催化的均丙醇的官能化：二和三取代的异恶唑烷和β-氨基-δ-羟基酯的简便合成

  摘要：

  对映体纯的Boc保护的烷氧基胺12和13通过易于转化的或保留构型的反应从易得的均丙醇4衍生而来，进行非对映选择性的Pd催化的闭环羰基酰胺化反应生成异恶唑烷16/17（≤50 1：1的非对映异构体比率（dr）可以很容易地转化为N -Boc保护的β-氨基-δ-羟基酸的酯及其γ取代的同系物37。关键的羰基化环化过程是通过跨CC键的钯和氮亲核试剂的不寻常的顺式加成而进行的（19 → 21），如15的反应所揭示，得到具有高非对映选择性的异恶唑烷18。

  DOI：

  10.1002/chem.201102716

文献信息

• Use of Aryl Chlorides as Electrophiles in Pd-Catalyzed Alkene Difunctionalization Reactions
  作者：Brandon R. Rosen、Joshua E. Ney、John P. Wolfe

  DOI：10.1021/jo100344k

  日期：2010.4.16

  The development of conditions that allow use of inexpensive aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and carboetherification reactions is described. A catalyst composed of Pd(OAc)2 and S-Phos minimizes N-arylation of the substrate and prevents formation of mixtures of regioisomeric products. A number of heterocycles, including pyrrolidines, isoxazolidines, tetrahydrofurans

  描述了允许在Pd催化的烯烃碳氨化和碳醚化反应中使用廉价的芳基氯化物作为亲电子试剂的条件的开发。由Pd（OAc）2和S-Phos组成的催化剂可最大程度地减少底物的N-芳基化并防止形成区域异构产物的混合物。用这种方法可有效地产生许多杂环，包括吡咯烷，异恶唑烷，四氢呋喃和吡唑烷。
• Allylation Reactions of N,O-Heterocycles
  作者：Roderick Bates、Chi Tang、Yuting Tan、Siti Buang

  DOI：10.1055/s-0031-1290458

  日期：——

  Iminium ions generated from isoxazolidines and tetrahydro-1,2-oxazines undergo allylation under Sakurai conditions. Allylated isoxazolidines are formed predominantly as the trans isomer, while oxazines are formed exclusively as the cis isomer.

  由异恶唑烷和四氢-1,2-恶嗪生成的亚胺离子在 Sakurai 条件下发生烯丙基化。烯丙基化异恶唑烷主要以反式异构体形式形成，而恶嗪仅以顺式异构体形式形成。
• Synthesis of N,O-Heterocycles by Intramolecular Conjugate Addition of a Hydroxylamine
  作者：Roderick Bates、Robert Snell、SusAnn Winbush

  DOI：10.1055/s-2008-1072650

  日期：——

  Isoxazolidines and tetrahydro-1,2-oxazines were produced by a tandem deprotection-intramolecular Michael addition of hydroxylamines. For tetrahydrooxazine formation, high stereoselectivity was observed, even when a quaternary centre was formed.

  异恶唑烷和四氢-1,2-恶嗪是通过羟胺的串联脱保护-分子内迈克尔加成产生的。对于四氢恶嗪的形成，观察到高立体选择性，即使形成了四元中心。
• Influence of Hydroxylamine Conformation on Stereocontrol in Pd-Catalyzed Isoxazolidine-Forming Reactions
  作者：Georgia S. Lemen、Natalie C. Giampietro、Michael B. Hay、John P. Wolfe

  DOI：10.1021/jo8027399

  日期：2009.3.20

  Palladium-catalyzed carboamination reactions between N-Boc-O-(but-3-enyl)hydroxylamine derivatives and aryl or alkenyl bromides afford cis-3,5- and trans-4,5-disubstituted isoxazolidines in good yield with up to >20:1 dr. The diastercoselectivity observed in the formation of cis-3,5-disubstituted isoxazolidines is superior to selectivities typically obtained in other transformations, such as 1,3-dipolar cycloaddition reactions, that provide these products. In addition, the stereocontrol in the C-N bond-forming Pd-catalyzed carboamination reactions of N-Boc-O-(but-3-enyl)hydroxylamines is significantly higher than that of related C-O bond-forming carboetherification reactions of N-benzyl-N-(but-3-enyl)hydroxylamine derivatives. This is likely due to a stereoelectronic preference for cyclization via transition states in which the Boc group is placed in a perpendicular orientation relative to the plane of the developing ring, which derives from the conformational equilibria of substituted hydroxylamines.
• Palladium-Catalyzed Ring-Forming Alkene Aminoaroylation of Unsaturated Hydrazones and Sulfonamides
  作者：Jun Chen、Meng-Nan Yang、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1021/acs.orglett.8b01208

  日期：2018.6.1

  The first example of a Pd(OAc)(2)-catalyzed ring-forming alkene aminoaroylation of unsaturated hydrazones and sulfonamides is described. This protocol features the use of diaryliodonium salts as both oxidants and aryl sources, thus enabling mild reaction conditions, good chemoselectivity, a broad substrate scope, and high functional group tolerance. A wide range of synthetically and biologically important functionalized dihydropyrazoles and isoxazolidines have been obtained in good yields.