N-(2-丙烯基)-N-叔丁基丙烯酰胺 | 116628-43-4

• 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: N-(2-丙烯基)-N-叔丁基丙烯酰胺
• 英文名称: N-(2-Propenyl)-N-tert-butylacrylamide
• 英文别名: N-allyl-N-(tert-butyl)acrylamide；N-allyl-N-tert-butyl-acrylamide；N-tert-Butyl-N-allyl-acrylamid；N-tert-butyl-N-(prop-2-en-1-yl)prop-2-enamide；N-tert-butyl-N-prop-2-enylprop-2-enamide
• CAS: 116628-43-4
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: XOPWGEGZEKLLMR-UHFFFAOYSA-N

物化性质

• 沸点：
  261.7±19.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-丙烯基)-N-叔丁基丙烯酰胺 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 反应 86.5h， 生成 1-(2,2-diethyl-butyryl)-3-methyl-2-(3-oxopropyl)-pyrrolidine-3-carboxy;ic acid tert-butylamide
  参考文献：
  名称：

  Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides

  摘要：

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.

  DOI：

  10.1021/ol0364071
• 作为产物：
  描述：

  N-叔丁基丙烯酰胺 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以46%的产率得到N-(2-丙烯基)-N-叔丁基丙烯酰胺
  参考文献：
  名称：

  Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides

  摘要：

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.

  DOI：

  10.1021/ol0364071

文献信息

• Visible Light‐Mediated Synthesis of Enantiopure γ‐Cyclobutane Amino and 3‐(Aminomethyl)‐5‐phenylpentanoic Acids
  作者：Sabine Kerres、Eva Plut、Simon Malcherek、Julia Rehbein、Oliver Reiser

  DOI：10.1002/adsc.201801413

  日期：2019.3.15

  Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into γ‐cyclobutane amino acids.

  可见光介导的[2 + 2]使用的[Ir（DTB-联吡啶）（DF（CF酰胺连接的二烯的光环3）PPY）2 ] PF 6作为三重态敏化剂施加到生成各种ñ -叔-丁基，ñ苄基和ñ -叔丁氧羰基保护的3-氮杂双环[3.2.0]庚烷-2-酮以良好的收率和良好的非对映选择性。密度泛函理论计算为[2 + 2]光环加成反应的构象先决条件提供了启示。双环键结构很容易转化为γ-环丁烷氨基酸。
• Chemoselective ring construction from unsymmetrical 1,6-dienes via radical addition of sulfonyl halides
  作者：I. De Riggi、S. Gastaldi、J. M. Surzur、M. P. Bertrand、Albert Virgili

  DOI：10.1021/jo00049a014

  日期：1992.11

  The sulfonyl radical-promoted cyclizations of 1,6-unsymmetrical dienes can be totally chemoselective. The addition of tosyl halides to various 1,6-dienes bearing both a nucleophilic and an electrophilic double bond clearly indicates that this attractive property is not related to the generally accepted electrophilic nature of tosyl radical. The chemoselectivity is likely to originate from the reversibility of the first step, i.e. tosyl radical addition to the double bond, which favors the formation of the adducts resulting from the one intermediate radical that cyclizes faster.
• Schmitz,E. et al., Journal fur praktische Chemie (Leipzig 1954), 1976, vol. 318, p. 471 - 478
  作者：Schmitz,E. et al.

  DOI：——

  日期：——
• Chemoselective Lactam Formation in the Addition of Benzenesulfonyl Bromide to <i>N</i>-Allyl Acrylamides and <i>N</i>-Allyl 3,3-Dimethylacrylamides
  作者：Chen Wang、Glen A. Russell

  DOI：10.1021/jo9820770

  日期：1999.4.1

  Chemoselectivity in the addition and cyclization reactions of PhSO2Br to N-allyl acrylamides has been confirmed due to the higher reactivity of the acrylic C=C bond toward the sulfonyl radical than that of the allyl C=C bond. Formation of gamma-lactams by C-beta-->C-alpha, cyclization can be achieved with N-allyl 3,3-dimethylacrylamides.
• De Riggi I., Gastaldi S., Surzur J.-M., Bertrand M. P., Virgili Albert, J. Org. Chem., 57 (1992) N 23, S 6118-6125
  作者：De Riggi I., Gastaldi S., Surzur J.-M., Bertrand M. P., Virgili Albert

  DOI：——

  日期：——