N-benzyloxycarbonyl-1-(4-nitrophenyl)but-3-enylamine | 187974-75-0

• 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: N-benzyloxycarbonyl-1-(4-nitrophenyl)but-3-enylamine
• 英文别名: benzyl (1-(4-nitrophenyl)but-3-en-1-yl)carbamate；benzyl 1-(4-nitrophenyl)but-3-enylcarbamate；Carbamic acid, [1-(4-nitrophenyl)-3-butenyl]-, phenylmethyl ester；benzyl N-[1-(4-nitrophenyl)but-3-enyl]carbamate
• CAS: 187974-75-0
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: IUYCTIOXUWXGQX-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  507.3±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  carbonic acid (Z)-4-methoxycarbonyloxy-but-2-enyl ester methyl ester 、 N-benzyloxycarbonyl-1-(4-nitrophenyl)but-3-enylamine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以52%的产率得到(E)-benzyl 5-(methoxycarbonyloxy)-1-(4-nitrophenyl)pent-3-enylcarbamate
  参考文献：
  名称：

  Stereodivergent Synthesis of 1,3-syn- and -anti-Tetrahydropyrimidinones

  摘要：

  An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines

  DOI：

  10.1021/ol101755m
• 作为产物：
  描述：

  benzyl N-[(4-methylphenyl)sulfonyl-(4-nitrophenyl)methyl]carbamate 、 烯丙基三甲基硅烷 在 三(五氟苯基)硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以81%的产率得到N-benzyloxycarbonyl-1-(4-nitrophenyl)but-3-enylamine
  参考文献：
  名称：

  Mild and Efficient Tris(pentafluorophenyl)borane-catalyzed Sakurai Allylation of N-Benzyloxycarbonylamino p-Tolylsulfone with Allyltrimethylsilane

  摘要：

  研究发现，三(五氟苯基)硼烷（$B(C_6F_5)_3$）是一种高效催化剂，可利用烯丙基三甲基硅烷对 N-苄氧羰基氨基对甲苯磺酸进行樱井烯丙基化，从而合成 N-苄基烯丙基胺。

  DOI：

  10.5012/bkcs.2012.33.4.1275

文献信息

• Gallium(III) Chloride-catalyzed Sakurai Reaction of α-Amido Sulfones with Allyltrimethylsilane: Access to Synthesis of 2,6-Disubstituted Piperidine Alkaloid Derivatives
  作者：R. Sateesh Chandra Kumar、G. Venkateswar Reddy、K. Suresh Babu、J. Madhusudana Rao

  DOI：10.1246/cl.2009.564

  日期：2009.6.5

  of N-alkoxycarbonylamino sulfones (α-amido sulfones) with allyltrimethylsilane in the presence of gallium(III) chloride (5 mol %) proceeded smoothly to afford the corresponding protected homoallylamines in high yields (82―96%). As an application of this methodology, two-step synthesis of biologically active natural products, 2,6-disubstituted piperidine alkaloid derivatives was carried out.

  N-烷氧基羰基氨基砜（α-酰氨基砜）与烯丙基三甲基硅烷在氯化镓（III）（5 mol %）存在下的樱井反应顺利进行，以高产率（82-96%）得到相应的保护高烯丙胺。作为该方法的应用，进行了生物活性天然产物 2,6-二取代哌啶生物碱衍生物的两步合成。
• FeSO₄·7H₂O-Catalyzed Four-Component Synthesis of Protected Homoallylic Amines
  作者：Qi-Yi Song、Bai-Ling Yang、Shi-Kai Tian

  DOI：10.1021/jo0704558

  日期：2007.7.1

  An efficient catalytic four-component reaction of carbonyl compounds (or acetals/ketals), benzyl chloroformate (CbzCl), 1,1,1,3,3,3-hexamethyldisilazane (HMDS), and allyltrimethylsilane has been successfully developed to produce Cbz-protected homoallylic amines in the presence of 5 mol % of iron(II) sulfate heptahydrate (FeSO4·7H2O), an inexpensive and environmentally friendly catalyst, at room temperature

  已成功开发了羰基化合物（或缩醛/缩酮），氯甲酸苄酯（CbzCl），1,1,1,3,3,3-六甲基二硅氮烷（HMDS）和烯丙基三甲基硅烷的高效催化四组分反应，可生产Cbz-在室温下，在5摩尔％的七水合硫酸铁（II）（FeSO 4 ·7H 2 O）（一种廉价的环境友好型催化剂）的存在下，保护被保护的均烯丙基胺。
• Re2O7-catalyzed three-component synthesis of protected secondary and tertiary homoallylic amines
  作者：Suman Pramanik、Prasanta Ghorai

  DOI：10.1039/c2cc15472b

  日期：——

  Three-component synthesis of protected secondary and "for the first time" tertiary homoallylic amines is achieved from carbonyl, carbamate, and allyltrimethylsilanes using a Re(2)O(7)-catalyst under mild and open flask conditions. Excellent chemoselectivities and diastereoselectivities were observed.

  在温和和开放的烧瓶条件下，使用Re（2）O（7）催化剂由羰基，氨基甲酸酯和烯丙基三甲基硅烷实现受保护的仲和“首次”叔均烯丙基胺的三组分合成。观察到优异的化学选择性和非对映选择性。
• Phosphomolybdic Acid-Catalyzed Efficient Three-Component Reaction: A Facile Synthesis of Protected Homoallylic Amines
  作者：John S. Williamson、G. Smitha、Bruhaspathy Miriyala

  DOI：10.1055/s-2005-863723

  日期：——

  A new and efficient phosphomolybdic acid (H 3 PMo 1 2 O 4 0 )-catalyzed three-component reaction of aldehydes, carbamate and allyltrimethylsilane to yield the corresponding protected homoallylic amines in good yields is described.

  描述了一种新的和有效的磷钼酸 (H 3 PMo 1 2 O 4 0 )-催化醛、氨基甲酸酯和烯丙基三甲基硅烷的三组分反应，以良好的产率得到相应的受保护的高烯丙基胺。
• Magnesium Bistrifluoromethanesulfonimide Catalysed Three-Component Synthesis of Protected Homoallylic Amines
  作者：Hongshe Wang、Weixing Zhao

  DOI：10.3184/174751911x13056175312712

  日期：2011.5

  A one-pot, three-component reaction of an aldehyde, benzyl carbamate and allyltrimethylsilane in the presence of 3 mol% of magnesium bistrifluoromethanesulfonimide at room temperature has been shown to afford the corresponding protected homoallylic amine in high yield.

  在室温下在 3 mol% 双三氟甲磺酰亚胺镁存在下，醛、氨基甲酸苄酯和烯丙基三甲基硅烷的一锅三组分反应已被证明可以高产率地提供相应的受保护的高烯丙基胺。