propane-1,3-diacetamide | 15762-68-2

• 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: propane-1,3-diacetamide
• 英文别名: N,N'-propanediyl-bis-acetamide；N,N'-Propandiyl-bis-acetamid；1,3-diaminopropane bis-acetamide；N-(3-acetamidopropyl)acetamide
• CAS: 15762-68-2
• 化学式: C₇H₁₄N₂O₂
• mdl: MFCD00048200
• 分子量: 158.2
• InChiKey: ZKNABVGKDQELOH-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±28.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  propane-1,3-diacetamide 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N,N'-Dimethyl-N,N'-diacetylpropan-1,3-diamin
  参考文献：
  名称：

  Lead optimization of HMBA to develop potent HEXIM1 inducers

  摘要：

  The potency of a series of Hexamethylene bis-acetamide (HMBA) derivatives inducing Hexamethylene bis-acetamide inducible protein 1 (HEXIM1) was determined in LNCaP prostate cancer cells. Several compounds with unsymmetrical structures showed significantly improved activity. Distinct from HMBA, these analogs have increased hydrophobicity and can improve the short half-life of HMBA, which is one of the factors that have limited the application of HMBA in clinics. The unsymmetrical scaffolds of the new analogs provide the basis for further lead optimization of the compounds using combinatorial chemistry strategy. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.025
• 作为产物：
  描述：

  溶剂黄146 、 1,3-丙二胺 在 sulfonic group functionalized polyacrylonitrile preoxidated nanofiber mat 作用下， 反应 3.0h， 以84.98%的产率得到propane-1,3-diacetamide
  参考文献：
  名称：

  Sulfonic groups functionalized preoxidated polyacrylonitrile nanofibers and its catalytic applications

  摘要：

  A SO3H-bearing nanofiber mat was synthesized and investigated as a novel heterogeneous acid catalyst. Preoxidated polyacrylonitrile nanofiber mat was prepared via electrospinning and heat treatment, and then reacted with chlorosulfuric acid to introduce the sulfonic groups. The nanofiber mat owned high acidity of 2.99 mmol/g. The preoxidation and sulfonation were examined by FT-IR spectroscopy. elemental analysis and X-ray diffraction spectroscopy (XRD). The fiber morphologies were characterized by scanning electron microscopy (SEM). The catalytic activities and reuse of the prepared nanofiber mat solid acid catalyst have been evaluated for the acetalization and esterification. The regular fiber mat structure could significantly facilitate the recovery and reuse of the catalyst. The excellent catalytic performance and easy recycling made the novel fiber mat solid acid hold great potential for the green chemical processes. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2012.07.034

文献信息

• Amide exchange reaction: a simple and efficient CuO catalyst for diacetamide synthesis
  作者：Qinghe Li、Peixue Wang、Youquan Deng

  DOI：10.1039/c6ra05563j

  日期：——

  A highly copper-catalysed amide exchange reaction of hexamethylenediamine (HDA) with CH3CN and H2O for the synthesis of hexamethylenebisacetamide (HMBA) without an organic solvent or gas protection was developed. 100% HDA conversion and >99% HMBA selectivity was obtained. X-ray diffraction, scanning emission microscopy, and temperature-programmed reduction of hydrogen were used to characterize the

  开发了一种高度铜催化的六亚甲基二胺（HDA）与CH 3 CN和H 2 O的酰胺交换反应，无需有机溶剂或气体保护即可合成六亚甲基双乙酰胺（HMBA）。获得了100％的HDA转化率和> 99％的HMBA选择性。X射线衍射，扫描电子显微镜和程序升温还原氢气被用来表征催化剂的结构特性。还研究了反应机理。
• Tetranuclear [Mn^IIIMn₃^IVO₄] Complexes as Spectroscopic Models of the S₂ State of the Oxygen Evolving Complex in Photosystem II
  作者：Heui Beom Lee、Angela A. Shiau、Paul H. Oyala、David A. Marchiori、Sheraz Gul、Ruchira Chatterjee、Junko Yano、R. David Britt、Theodor Agapie

  DOI：10.1021/jacs.8b09961

  日期：2018.12.12

  structure-electronic structure studies remain rare. Herein, we report the synthesis, crystal structure, electrochemistry, XAS, magnetic susceptibility, variable temperature CW-EPR, and pulse EPR data for a series of [MnIIIMn3IVO4] cuboidal complexes as spectroscopic models of the S2 state of the OEC. Resembling the oxidation state and EPR spectra of the S2 state of the OEC, these model complexes show two EPR signals

  尽管进行了广泛的生化、光谱和计算研究，但光系统 II 的析氧复合物 (OEC) 的生物水氧化机制仍然是一个重大争论的主题。机制建议由反应中间体的表征指导，例如 S2 状态，其在 g = 2 和 g = 4.1 处具有两个特征 EPR 信号。两种几乎等能的结构异构体已被提议作为这些不同信号的来源，但相关的结构-电子结构研究仍然很少。在此，我们报告了一系列 [MnIIIMn3IVO4] 长方体配合物的合成、晶体结构、电化学、XAS、磁化率、可变温度 CW-EPR 和脉冲 EPR 数据，作为 OEC S2 状态的光谱模型。类似于 OEC 的 S2 状态的氧化态和 EPR 光谱，这些模型复合物显示了两个 EPR 信号，一个宽低场信号和一个多线信号，它们与生物系统非常相似。研究了桥连配体性质的系统变化对光谱学的影响。结果表明，四核 Mn 配合物的电子结构对即使是很小的几何变化和桥接配体的性质也高度敏感。我们的模型研究表明，OEC
• Cooperative Binding of Divalent Diamides by<i>N</i>-Alkyl Ammonium Resorcinarene Chlorides
  作者：N. Kodiah Beyeh、Altti Ala-Korpi、Fangfang Pan、Hyun Hwa Jo、Eric V. Anslyn、Kari Rissanen

  DOI：10.1002/chem.201406504

  日期：2015.6.22

  N‐Alkyl ammonium resorcinarene chlorides, stabilized by an intricate array of hydrogen bonds leading to a cavitand‐like structure, bind amides. The molecular recognition occurs through intermolecular hydrogen bonds between the carbonyl oxygen and the amide hydrogen of the guests and the cation–anion circular hydrogen‐bonded seam of the hosts, as well as through CH⋅⋅⋅π interactions. The N‐alkyl ammonium

  N-烷基铵间苯二甲酰氯，通过复杂的氢键阵列（形成空泡状结构）而稳定，与酰胺结合。分子识别是通过客体的羰基氧和酰胺氢之间的分子间氢键以及主体的阳离子-阴离子圆氢键合接缝以及CH⋅⋅⋅π相互作用而发生的。所述Ñ烷基铵氯化物间苯二酚杯芳烃协同结合的一系列不同间隔长度从三至七个碳原子的二-乙酰胺的。取决于间隔物的长度，滴定数据适合1：1或2：1结合等温线。考虑到所有的客人具有相似的结合基序，第一结合常数相似（ķ 1：10 每个主机2 M -1）。第二结合常数被发现取决于宿主的上边缘取代基，客人的间隔长度，与六碳间隔结合所观察到的最佳（ķ 2：10 3 中号-2）。较短的间隔物长度会增加空间位阻，而较长的间隔物长度会增加柔韧性，从而降低协作性。具有刚性环己基上边缘的主体显示出比具有柔性苄基臂的主体更强的结合力。通过1 H NMR滴定研究在溶液中研究了这些二价客体的协同结合，并辅以扩散有序光谱法（DOSY），X射线晶体学和质谱法。
• Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis
  作者：Tatiana Golub、James Y Becker

  DOI：10.3762/bjoc.14.72

  日期：——

  monoamides upon anodic oxidation in methanol/LiClO4 because both types undergo majorly mono- and dimethoxylations at the α-position to the N atom. However, in cases where the spacer contains two methylene groups only the anodic process leads mostly to CH2-CH2 bond cleavage to afford products of type RCONHCH2OCH3. Moreover, upon replacing LiClO4 with Et4NBF4 an additional fragmentation type of product was generated

  通常，在甲醇/ LiClO4中进行阳极氧化时，衍生自二胺并涉及3和4个亚甲基作为两个酰胺官能团之间的间隔基的双酰胺的行为类似于单酰胺，因为这两种类型的酰胺都主要在N原子的α位发生单-和二甲氧基化。 。但是，在间隔基包含两个亚甲基的情况下，仅阳极过程主要导致CH2- 键断裂，从而提供RCONH OCH3类型的产物。此外，用Et4NBF4代替LiClO4时，后者的酰胺（即RCONHCHO）产生了另一种片段化产物。同样，发现阳极氧化工艺以C毡为阳极，并以1：1甲醇/乙腈助溶剂的混合物进行时，效率更高。
• Selective Monoderivatization of Propane-1,3-diamine with Acid Chlorides: ?Hexahydropyrimidine method?vs. statistic methods
  作者：Christian Jentgens、Stefan Bienz、Manfred Hesse

  DOI：10.1002/hlca.19970800410

  日期：1997.6.30

  The selective N-monoderivatization of propane-1,3-diamine (5) with carbonyl and sulfonyl chlorides via2-phenylhexahydropyrimidine (6) was compared with the direct statistic monoderivatization. It was found that, under optimized conditions, both methods are competitive to one another, depending, however, strongly on the reactivity of the eleclrophile used. The ‘hexahydropyrimidine method’ is more reliable

  将丙烷1，，3-二胺（5）与羰基和磺酰氯经2-苯基六氢嘧啶（6）的选择性N-单衍生化与直接统计单衍生化进行了比较。已经发现，在优化的条件下，两种方法彼此竞争，但是，这在很大程度上取决于所用亲电子试剂的反应性。就产量而言，“六氢嘧啶法”更为可靠，中等，但始终在54％至69％之间，而在某些情况下，“统计法”可导致极高的产率（高达96％），而在其他情况下，几乎没有。