N-acetyl-1-azido-3-aminopropane | 92954-42-2

• 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
• 英文名称: N-acetyl-1-azido-3-aminopropane
• 英文别名: N-(3-azidopropyl)acetamide
• CAS: 92954-42-2
• 化学式: C₅H₁₀N₄O
• 分子量: 142.161
• InChiKey: IOHNUYAUYKRLEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-acetyl-1-azido-3-aminopropane 在 palladium on activated charcoal 盐酸 、 甲醇 、 sodium azide 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 25.0~80.0 ℃ 、413.69 kPa 条件下， 反应 48.17h， 生成 N(1)-乙酰基去甲亚精胺
  参考文献：
  名称：

  Aliphatic amino azides as key building blocks for efficient polyamine syntheses

  摘要：

  New routes to open-chain polyamines have been developed using aliphatic amino azides as common precursors for the construction of the carbon-nitrogen framework. These alpha,omega-diaminoalkane synthetic equivalents were combined with (omega-halogenoalkyl)dichloroboranes to extend the polyamine chain from the azido moiety. An extension from the free amino group can also be achieved via a Michael type addition with acrylonitrile or a reductive amination with a gamma-azido ketone. Further transformations led to a large variety of regioselectively C- or (and) N-substituted polyamines.

  DOI：

  10.1021/jo00066a028
• 作为产物：
  描述：

  2-methyl-(4H)-5,6-dihydro-1,3-oxazine 、 叠氮基三甲基硅烷 以 甲醇 为溶剂， 反应 5.0h， 以99%的产率得到N-acetyl-1-azido-3-aminopropane
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF SECONDARY CARBOXAMIDES WITH ω-SUBSTITUTED ETHYL AND PROPYL GROUPS ON NITROGEN ATOM BY NUCLEOPHILIC RING OPENING OF CYCLIC IMIDATES

  摘要：

  已开发出一种高效的合成方法，用于合成含ω-取代乙基和丙基的仲酰胺类化合物，该方法突出了2-甲基-2-氧杂环丁烷、2-甲基-2-氧嗪及其衍生物与(CH3)3SiX和HX（X=Cl, 叠氮, 苯硒基, 苯硫基）类型试剂的亲核开环反应。

  DOI：

  10.1246/cl.1984.1243

文献信息

• Iminium-functionalized 1,2,3-triazoles by [3+2] cycloaddition reactions of internal acetylenic iminium triflates with organoazides
  作者：Christian J. Tontsch、Holger Gerster、Gerhard Maas

  DOI：10.1515/znb-2019-0079

  日期：2019.8.27

  triflates 1–6 react as dipolarophiles in thermal [3 + 2]-cycloadditions with sufficiently electron rich organoazides to form 1,4,5-trisubstituted 1,2,3-triazoles with iminium functionalization. The reactions require rather strong thermal activation, but can be accelerated by microwave irradiation. The regioselectivity of the cycloaddition at the internal acetylenic bond of 3-cyclopropylpropyne and 3-arylpropyne

  摘要 丙炔亚胺三氟甲磺酸酯 1-6 作为偶极亲和体在热 [3 + 2]-环加成反应中与足够富电子的有机叠氮化物反应，形成具有亚胺功能化的 1,4,5-三取代 1,2,3-三唑。反应需要相当强的热活化，但可以通过微波辐射加速。3-环丙基丙炔和 3-芳基丙炔亚胺离子（分别为 1-3 和 4）的内部炔键的环加成的区域选择性非常高，但在亚胺离子的另一端存在空间要求高的取代基时会降低-取代的C，C三键。亚胺官能化的三唑很容易转化为中性化合物；本文报道了通过水解形成三唑基酮10和通过LiAlH 4 还原形成叔三唑基二甲基胺12。
• A Photoinduced, Benzyne Click Reaction
  作者：Adam W. Gann、Jon W. Amoroso、Vincent J. Einck、Walter P. Rice、James J. Chambers、Nathan A. Schnarr

  DOI：10.1021/ol500389t

  日期：2014.4.4

  The [3 + 2] cycloaddition of azides and alkynes has proven invaluable across numerous scientific disciplines for imaging, cross-linking, and site-specific labeling among many other applications. We have developed a photoinitiated, benzyne-based [3 + 2] cycloaddition that is tolerant of a variety of functional groups as well as polar, protic solvents. The reaction is complete on the minute time scale using a single equivalent of partner azide, and the benzyne photo-precursor is stable for months under ambient light at room tempurature. Herein we report the optimization and scope of the photoinitiated reaction as well as characterization of the cycloaddition products.
• SAITO, SEIKI;TAMAI, HIDEAKI;USUI, YUKI;INABA, MASAMI;MORIWAKE, TOSHIO, CHEM. LETT., 1984, N 7, 1243-1246
  作者：SAITO, SEIKI、TAMAI, HIDEAKI、USUI, YUKI、INABA, MASAMI、MORIWAKE, TOSHIO

  DOI：——

  日期：——
• Aliphatic amino azides as key building blocks for efficient polyamine syntheses
  作者：Bertrand Carboni、Aziza Benalil、Michel Vaultier

  DOI：10.1021/jo00066a028

  日期：1993.7

  New routes to open-chain polyamines have been developed using aliphatic amino azides as common precursors for the construction of the carbon-nitrogen framework. These alpha,omega-diaminoalkane synthetic equivalents were combined with (omega-halogenoalkyl)dichloroboranes to extend the polyamine chain from the azido moiety. An extension from the free amino group can also be achieved via a Michael type addition with acrylonitrile or a reductive amination with a gamma-azido ketone. Further transformations led to a large variety of regioselectively C- or (and) N-substituted polyamines.
• EFFICIENT SYNTHESIS OF SECONDARY CARBOXAMIDES WITH ω-SUBSTITUTED ETHYL AND PROPYL GROUPS ON NITROGEN ATOM BY NUCLEOPHILIC RING OPENING OF CYCLIC IMIDATES
  作者：Seiki Saito、Hideaki Tamai、Yuki Usui、Masami Inaba、Toshio Moriwake

  DOI：10.1246/cl.1984.1243

  日期：1984.7.5

  An efficient synthesis of secondary carboxamides carrying ω-substituted ethyl and propyl groups on nitrogen atom has been developed which highlights nucleophilic ring opening of 2-methyl-2-oxazoline, 2-methyl-2-oxazine, and their derivatives with (CH3)3SiX and HX (X= Cl, N3, SeC6H5, SC6H5) type reagents.

  已开发出一种高效的合成方法，用于合成含ω-取代乙基和丙基的仲酰胺类化合物，该方法突出了2-甲基-2-氧杂环丁烷、2-甲基-2-氧嗪及其衍生物与(CH3)3SiX和HX（X=Cl, 叠氮, 苯硒基, 苯硫基）类型试剂的亲核开环反应。