N-(3-甲基-2-丁烯-1-基)-乙酰胺 | 73286-69-8

• 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-(3-甲基-2-丁烯-1-基)-乙酰胺
• 中文别名: 6-甲氧基-3,3-二甲基铟烷-5-醇
• 英文名称: N-(3-methylbut-2-en-1-yl)acetamide
• 英文别名: 1-acetylamino-3-methyl-2-butene；N-(3-methyl-2-butenyl)acetamide；N-(3,3-Dimethylallyl)acetamide；4-Acetamido-2-methylbut-2-ene；N-(3-methyl-2-butenyl)-acetamide；N-(3-methylbut-2-enyl)acetamide
• CAS: 73286-69-8
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: HMFQZRAOCARFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3-甲基-2-丁烯-1-基)-乙酰胺 以39%的产率得到
  参考文献：
  名称：

  Ramalingam K., Zeng W., Nanjappan P., Nowotnik D. P., Synth. Commun, 25 (1995) N 5, S 743-752

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3-methylbut-2-enyl)-N-(2-phenylselanylethyl)acetamide 在 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 mercury(II) diacetate 、 二乙胺 作用下， 反应 0.25h， 生成 N-(3-甲基-2-丁烯-1-基)-乙酰胺
  参考文献：
  名称：

  New synthesis of secondary carboxamide by using 2-methyl-2-oxazoline as a building block

  摘要：

  DOI：

  10.1016/s0040-4039(00)98160-7

文献信息

• Cobalt(II) chloride catalysed conversion of allylic alcohols to rearranged allylic amides
  作者：Naresh K. Nayyar、M. Madhava Reddy、Javed Iqbal

  DOI：10.1016/0040-4039(91)80456-g

  日期：1991.11

  Secondary and tertiary allylic alcohols can be converted to the corresponding allylically rearranged amides and acetates in presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas the secondary ones yield a mixture of regioisomers.

  可以在催化量的氯化钴（II）和乙酸酐在乙腈中存在的情况下，将仲和叔烯丙基醇转化为相应的烯丙基重排的酰胺和乙酸酯。叔醇进行完全重排，而仲醇产生区域异构体的混合物。
• Silver Salt-Mediated Allylation Reactions Using Allyl Bromides
  作者：Xiaodong Xiong、Jonathan Wong、Ying-Yeung Yeung

  DOI：10.1021/acs.joc.1c00480

  日期：2021.5.7

  A facile, efficient, and chemoselective synthesis of allylic amides has been developed. Allyl bromides were used as the precursors activated by silver triflate. A Ritter-type reaction readily proceeded to give various allyl amides under mild conditions. The reaction protocol was also applicable to different nucleophilic partners to give a wide range of allyl-substituted products in the absence of a

  已经开发了一种简便，有效和化学选择性的烯丙基酰胺合成方法。烯丙基溴用作被三氟甲磺酸银活化的前体。在温和条件下，容易进行Ritter型反应，得到各种烯丙基酰胺。该反应方案也适用于不同的亲核配偶体，在不存在碱的情况下得到各种各样的烯丙基取代的产物。
• Galegine and a new dihydroxyalkylacetamide from Verbesina enceloiodes
  作者：John V. Eichholzer、Ivor A.S. Lewis、John K. Macleod、Peter B. Oelrichs、Peter J. Vallely

  DOI：10.1016/0031-9422(82)80021-6

  日期：1982.1

  The toxic principle from Verbesina enceloiodes has been identified as galegine (3-methyl-2-butenylguanidine). A novel co-occurring non-toxic extrac

  Verbesina enceloiodes 的毒性原理已被确定为galegine（3-甲基-2-丁烯基胍）。一种新型共生无毒提取物
• Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles
  作者：Manoj Mukhopadhyay、M. Madhava Reddy、G. C. Maikap、Javed Iqbal

  DOI：10.1021/jo00114a013

  日期：1995.5

  Various secondary allylic alcohols or their acetates and tertiary allylic alcohols can be converted to the corresponding transposed allylic amides in the presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas secondary ones afford a mixture of regioisomers. Moderate yields of amides are also obtained by reacting acrylonitrile with secondary alcohols in 1,2-dichloroethane. The presence of acetic anhydride or acetic acid is crucial to the formation of amides as the absence of the former affords no amides and the allylic alcohols are mainly recovered as regioisomeric mixtures. The regioselectivity during amide formation can be enhanced by using cobalt complexes 14-16 in acetic acid medium. Some preliminary studies indicate that these reactions are proceeding via an pi-allyl complex or tight ion pair rather than a [3,3] sigmatropic rearrangement of acetamidate obtained in a Pinner reaction.
• Isomerization of N-allylamides and -imides to aliphatic enamides by iron, rhodium, and ruthenium complexes
  作者：J. K. Stille、Y. Becker

  DOI：10.1021/jo01299a021

  日期：1980.5