2-甲基-2-丙基(1E)-1-丙烯-1-基氨基甲酸酯 | 131971-64-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-甲基-2-丙基(1E)-1-丙烯-1-基氨基甲酸酯
• 英文名称: t-butyl prop-1-en-1-ylcarbamate
• 英文别名: 1-[(tert-butoxycarbonyl)amino]prop-1-ene；2-Methyl-2-propanyl (1E)-1-propen-1-ylcarbamate；tert-butyl N-prop-1-enylcarbamate
• CAS: 131971-64-7
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: FIZCCQCDGGYKLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基(1E)-1-丙烯-1-基氨基甲酸酯 、 benzaldehyde N-boc imine 在 三甲基氯硅烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到tert-butyl N-[(E)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylprop-2-enyl]carbamate
  参考文献：
  名称：

  Trimethylchlorosilane-promoted aza-Mannich reaction of enecarbamates and aldimines

  摘要：

  A trimethylchlorosilane-promoted aza-Mannich reaction is reported utilizing enecarbamates as the nucleophile and aromatic N-Boc aldimines as the electrophile. A variety of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering the adduct products in excellent yields with high E-stereoselectivities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.097
• 作为产物：
  描述：

  tert-butyl N-<1-((p-methylphenyl)sulfonyl)propyl>carbamate 在 三乙烯二胺 、 丙烯酸甲酯（MA） 作用下， 反应 336.0h， 以72%的产率得到2-甲基-2-丙基(1E)-1-丙烯-1-基氨基甲酸酯
  参考文献：
  名称：

  N-Carbamate Protected α-Amidoalkyl-p-tolylsulfones: Convenient Substrates in the aza-Morita−Baylis−Hillman Reaction

  摘要：

  An efficient and practical one-pot approach to aza-Morita-Baylis-Hillman adducts has been developed. The reaction occurs between N-Boc or N-Cbz imines, generated in situ from stable and easy to handle N-Boc or N-Cbz protected alpha-amidoalkyl-p-tolysulfones, and electron-deficient alkenes in the presence of DABCO. The presented procedure eliminates the use of the relatively unstable N-carbamate imines prior to the coupling reaction. The reaction is limited to alpha-amidosulfones derived from aromatic and heteroaromatic aldehydes.

  DOI：

  10.1021/jo801616d

文献信息

• Manganese(<scp>iii</scp>) acetate-mediated direct C(sp²)–H-sulfonylation of enamides with sodium and lithium sulfinates
  作者：Philipp Kramer、Sara-Cathrin Krieg、Harald Kelm、Georg Manolikakes

  DOI：10.1039/c9ob00825j

  日期：——

  highly stereoselective access to (E)-β-amidovinyl sulfones in moderate to excellent yields. The reaction proceeds readily under mild conditions at room temperature and tolerates various sensitive functional groups. This process affords exclusively (E)-configurated β-amidovinyl sulfones independent of the starting material configuration. Moreover, a direct transformation of organolithium reagents and sulfur

  Mn（OAc）3介导的酰胺和氨基甲酸酯与亚磺酸钠和亚磺酸锂的氧化C（sp2）-H磺酰化反应。该操作简单的转化以中等至优异的产率提供了对（E）-β-酰胺基乙烯基砜的直接且高度立体选择性的获得。该反应在室温温和条件下容易进行，并能耐受各种敏感的官能团。该方法独立地提供了（E）-构型的β-酰胺基乙烯基砜，而与起始材料的构型无关。此外，描述了有机锂试剂和二氧化硫直接转化为β-酰胺基乙烯基砜。
• Relay Catalysis by a Metal-Complex/Brønsted Acid Binary System in a Tandem Isomerization/Carbon−Carbon Bond Forming Sequence
  作者：Keiichi Sorimachi、Masahiro Terada

  DOI：10.1021/ja807591m

  日期：2008.11.5

  one-pot tandem isomerization/carbon-carbon bond forming sequence catalyzed by a ruthenium complex/Brønsted acid binary system is demonstrated. The method enables the use of readily available allylamides to deliver reactive imines under relay catalysis using a binary catalytic system. Subsequent Brønsted acid catalyzed carbon-carbon bond forming reactions of the generated imines with nucleophilic components

  展示了由钌配合物/布朗斯台德酸二元体系催化的一锅串联异构化/碳-碳键形成序列。该方法能够使用容易获得的烯丙酰胺在使用二元催化系统的中继催化下递送反应性亚胺。随后的布朗斯台德酸催化生成的亚胺与亲核组分的碳-碳键形成反应，以良好的产率提供了 Friedel-Crafts 和 Mannich 产物。
• Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines
  作者：Wei-Yang Ma、Coralie Gelis、Damien Bouchet、Pascal Retailleau、Xavier Moreau、Luc Neuville、Géraldine Masson

  DOI：10.1021/acs.orglett.0c03947

  日期：2021.1.15

  cycloaddition of β-substituted ene- and thioenecarbamates as well as cyclic enamides with quinone diimides catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported. A wide variety of 2,3-disubstituted 2-aminoindolines, including polycyclic ones, were prepared in generally high yields (up to 98%) with moderate to complete diastereoselectivities and in most cases excellent enantioselectivities

  据报道，由BINOL和SPINOL衍生的磷酸催化β-取代的烯和硫代氨基甲酸酯以及对环二酰胺与醌二酰亚胺的高度对映和区域选择性（3 + 2）形式环加成反应。通常以高收率（高达98％），中等至完全非对映选择性以及大多数情况下极好的对映选择性（高达99％ee）制备各种2，3-二取代的2-氨基二氢吲哚，包括多环吲哚。
• Iron(III)-Mediated Oxysulfonylation of Enamides with Sodium and Lithium Sulfinates
  作者：Philipp Kramer、Miro Halaczkiewicz、Yu Sun、Harald Kelm、Georg Manolikakes

  DOI：10.1021/acs.joc.9b03299

  日期：2020.3.6

  the oxysulfonylated products in moderate to excellent yields. Moreover, the direct incorporation of sulfur dioxide into the sulfonylated products via organolithium chemistry has been achieved. The formed N-O-acetals are competent acylimine precursors. Their utilization as building blocks for the synthesis of biologically relevant β-amidosulfones is described as well.

  描述了铁与亚氨基磺酸盐和醇的铁介导的邻位双官能化。该反应在温和的条件下进行，并以中等至极好的收率提供氧磺酰化产物。此外，已经实现了通过有机锂化学将二氧化硫直接掺入磺酰化产物中。所形成的NO-乙缩醛是合格的嘧啶前体。还描述了它们作为合成生物学上相关的β-氨基砜的基础材料的用途。
• A new method for the synthesis of N-t-butoxycarbonyl protected α-alkoxy amines from allylamines under neutral conditions
  作者：Hisao Nemoto、Hermogenes N. Jimenez、Yoshinori Yamamoto

  DOI：10.1039/c39900001304

  日期：——

  Treatment of the Boc protected allylamines (4) with rhodium catalysts in the presence of alcohols produces N-Boc substituted α-alkoxy amines (5) in high yields, which can be used as a synthetic equivalents of activated imines having an easily deprotectable Boc group.

  在醇存在下用铑催化剂处理Boc保护的烯丙胺（4）可以高收率生产N -Boc取代的α-烷氧基胺（5），可用作具有易于脱保护的Boc基团的活化亚胺的合成等价物。