2-(苯磺酰基)-N,N-二乙基乙酰胺 | 163019-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(苯磺酰基)-N,N-二乙基乙酰胺
• 英文名称: N,N-diethyl(phenylsulfonyl)acetamide
• 英文别名: 2-(benzenesulfonyl)-N,N-diethylacetamide
• CAS: 163019-28-1
• 化学式: C₁₂H₁₇NO₃S
• 分子量: 255.338
• InChiKey: KEAACMAWBWZGJR-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  435.7±37.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  咪唑[1,2-A]吡啶-2-甲醛 、 2-(苯磺酰基)-N,N-二乙基乙酰胺 在 sodium 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以68%的产率得到(E)-N,N-diethyl-3-(imidazo[1,2-a]pyrid-2-yl)-2-(phenylsulfonyl)propenamide
  参考文献：
  名称：

  Stereoselective synthesis of (E)-N,N-diethyl-3-(imidazo[1,2-a]pyrid-2-yl)-2-(phenylsulfonyl)propenamide

  摘要：

  The title compound, gem-amidovinylsulfone 3, was synthesized stereoselectively by aldolic condensation of N,N-diethylphenylsulfonylacetamide 1 on imidazo[1,2-a]pyridine-2-carbaldehyde 2 adding Et3N at the end. The X-ray crystal structure of 3 [C20H21N3O3S: M-r=383.5, monoclinic, P2(1), a = 8.191(4) Angstrom, b=21.132(2) Angstrom, c = 11.752(1) Angstrom, beta=96.40(2)degrees, V= 2022(1) Angstrom3, Z=4 (two molecules per asymmetric unit), D-calc,= 1.260 g cm(-3), a(Mo Ka) = 0.71073 A, mu = 0.184 mm(-1), F(000) = 808, T = 293(2) K, R = 0.059 for 5105 observed reflections with 1 greater than or equal to 2sigma(1)] was determined, and confirmed the (E) configuration. 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(01)00919-x
• 作为产物：
  描述：

  N,N-diethyl-2-(phenylthio)acetamide 在 selenium(IV) oxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 2-(苯磺酰基)-N,N-二乙基乙酰胺
  参考文献：
  名称：

  Spectroscopic and theoretical studies of some N,N-diethyl-2-[(4′-substituted)phenylsulfonyl]acetamides

  摘要：

  The analysis of the IR carbonyl band of the N,N-diethyl-2-[(4'-substituted)phenylsulfonyl]acetamides Et(2)NC(O)CH(2)S(O)(2)-C(6)H(4)-Y (Y = OMe 1, Me 2,1-13, Cl 4, Br 5, NO(2) 6) supported by B3LYP/6-31G(d,p) calculations for 3, indicated the existence of three pairs (anti and syn) of cis (c) and gauche (g(1) and g(2)) conformers in the gas phase, being the gauche conformers significantly more stable than the cis ones. The anti geometry is more stable than the syn one, for each pair of cis and gauche conformers. The summing up of the orbital (NBO analysis) and electrostatic interactions justifies quite well the populations and the v(CO) frequencies of the anti and syn pairs of c, g(1) and g(2) conformers. The IR higher carbonyl frequency component whose population is ca. 10%, in CCl(4), may be ascribed to the least stable and most polar cis conformer pair (in the gas phase) and the lower frequency component whose population is ca. 90%, to the summing up of the populations of the two most stable and least polar gauche conformer pairs (g(1) and g(2)) (in the gas phase). The reversal of the cis(c)/gauche (g(1) + g(2)) population ratio observed in chloroform ca. 60% (cis)/40% (gauche) and the occurrence of the most polar cis(c) conformer only, in acetonitrile, strongly suggests the coalescence of the two gauche components in a unique carbonyl band in solution. A further support to this rationalization is given by the single point PCM solvation model performed by HF/6-31G(d,p) method, which showed a progressive increase of the c/(g(1) + g(2)) ratio going from gas to CCl(4), to CHCl(3) and to CH(3)CN. X-ray single crystal analysis of 4 indicates that this compound assumes, in the solid state, the syn-clinal (gauche) conformation with respect to the [O=C-CH(2)-S] moiety, and the most stable anti geometry relative to the [C(O)N(CH(2)CH(3))(2)] fragment. In order to obtain larger energy gain from the crystal packing the molecules of 4 are linked in centrosymmetric dimers through two C-H center dot center dot center dot O interactions (C-H([O-Ph])center dot center dot center dot O([SO2])) forming a step ladder. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.06.051

文献信息

• Orthoamide und Iminiumsalze, CVII^a. 4-Sulfonylierte- und 4-phosphorylierte sowie 4-isocyansubstituierte-1,1-Bis(dimethylamino)-1,3-butadiene aus Sulfonen, (Alkyl)phosphonsäureestern sowie Isocyanessigsäureester und Orthoamid-Derivaten von Alkincarbonsäuren
  作者：Willi Kantlehner、Markus Vettel、Hansjörg Lehmann、Wolfgang Frey

  DOI：10.1515/znb-2022-0051

  日期：2022.12.16

  Ethoxycarbonyl-triphenylphosphonium bromide reacts with orthoamides of alkynecarboxylic acids 14 to give vinylogous guanidinium bromides, which were transformed to the corresponding tetraphenylborates. In contrast, from CH2-acidic phosphonicesters and orthoamides 14 phosphorylated 1,1-diamino-butadienes can be obtained. Two of these products rearrange to 5-dimethylamino-4-diet-hylphosphono-2,4-hexadienic

  摘要 乙氧羰基三苯基溴化膦与炔羧酸 14 的原酰胺反应，生成乙烯基溴化胍，并转化为相应的四苯基硼酸盐。相反，从 CH2- 酸性膦酸酯和原酰胺 14 中可以得到磷酸化的 1,1-二氨基丁二烯。其中两种产物在加热后重新排列为 5-二甲基氨基-4-二乙基膦酰基-2,4-己二烯酸酰胺。苯磺酰化羧酸和烷基酮与原酰胺 14 的反应在缩合作用下进行，生成 4-苯磺酰基-1,1-二氨基-1,3-丁二烯。因此，原酰胺 14 和异氰基乙酸酯之间的缩合反应生成 2-异氰基-5,5-双（二甲基氨基）-2,4-戊二烯酸酯。在其中一个反应中，副产物为 5,6-二氨基吡啶-2-羧酸酯。一些烯酮氨基化合物以立体异构体平衡混合物的形式存在，这是丁二烯单元顺式和反式异构的结果。
• A New Facile Synthesis of a Thromboxane B₂Precursor
  作者：Jozua F. Booysen、Cedric W. Holzapfel

  DOI：10.1080/00397919508011758

  日期：1995.5

  A short, stereocontrolled synthesis of a key intermediate in the synthesis of thromboxane B-2 is described. The approach is based on the use of N,N-diethyl(phenylsulfonyl)acetamide as nucleophile in a palladium-catalysed nucleophilic substitution reaction.
• Spectroscopic and theoretical studies of some N,N-diethyl-2-[(4′-substituted)phenylsulfonyl]acetamides
  作者：Elisângela Vinhato、Paulo R. Olivato、Alessandro Rodrigues、Julio Zukerman-Schpector、Maurizio Dal Colle

  DOI：10.1016/j.molstruc.2011.06.051

  日期：2011.9

  The analysis of the IR carbonyl band of the N,N-diethyl-2-[(4'-substituted)phenylsulfonyl]acetamides Et(2)NC(O)CH(2)S(O)(2)-C(6)H(4)-Y (Y = OMe 1, Me 2,1-13, Cl 4, Br 5, NO(2) 6) supported by B3LYP/6-31G(d,p) calculations for 3, indicated the existence of three pairs (anti and syn) of cis (c) and gauche (g(1) and g(2)) conformers in the gas phase, being the gauche conformers significantly more stable than the cis ones. The anti geometry is more stable than the syn one, for each pair of cis and gauche conformers. The summing up of the orbital (NBO analysis) and electrostatic interactions justifies quite well the populations and the v(CO) frequencies of the anti and syn pairs of c, g(1) and g(2) conformers. The IR higher carbonyl frequency component whose population is ca. 10%, in CCl(4), may be ascribed to the least stable and most polar cis conformer pair (in the gas phase) and the lower frequency component whose population is ca. 90%, to the summing up of the populations of the two most stable and least polar gauche conformer pairs (g(1) and g(2)) (in the gas phase). The reversal of the cis(c)/gauche (g(1) + g(2)) population ratio observed in chloroform ca. 60% (cis)/40% (gauche) and the occurrence of the most polar cis(c) conformer only, in acetonitrile, strongly suggests the coalescence of the two gauche components in a unique carbonyl band in solution. A further support to this rationalization is given by the single point PCM solvation model performed by HF/6-31G(d,p) method, which showed a progressive increase of the c/(g(1) + g(2)) ratio going from gas to CCl(4), to CHCl(3) and to CH(3)CN. X-ray single crystal analysis of 4 indicates that this compound assumes, in the solid state, the syn-clinal (gauche) conformation with respect to the [O=C-CH(2)-S] moiety, and the most stable anti geometry relative to the [C(O)N(CH(2)CH(3))(2)] fragment. In order to obtain larger energy gain from the crystal packing the molecules of 4 are linked in centrosymmetric dimers through two C-H center dot center dot center dot O interactions (C-H([O-Ph])center dot center dot center dot O([SO2])) forming a step ladder. (C) 2011 Elsevier B.V. All rights reserved.
• Stereoselective synthesis of (E)-N,N-diethyl-3-(imidazo[1,2-a]pyrid-2-yl)-2-(phenylsulfonyl)propenamide
  作者：S. Céard、D. Roche、V. Gaumet、D. Gardette、J. Métin、M. Madesclaire

  DOI：10.1016/s0022-2860(01)00919-x

  日期：2002.8

  The title compound, gem-amidovinylsulfone 3, was synthesized stereoselectively by aldolic condensation of N,N-diethylphenylsulfonylacetamide 1 on imidazo[1,2-a]pyridine-2-carbaldehyde 2 adding Et3N at the end. The X-ray crystal structure of 3 [C20H21N3O3S: M-r=383.5, monoclinic, P2(1), a = 8.191(4) Angstrom, b=21.132(2) Angstrom, c = 11.752(1) Angstrom, beta=96.40(2)degrees, V= 2022(1) Angstrom3, Z=4 (two molecules per asymmetric unit), D-calc,= 1.260 g cm(-3), a(Mo Ka) = 0.71073 A, mu = 0.184 mm(-1), F(000) = 808, T = 293(2) K, R = 0.059 for 5105 observed reflections with 1 greater than or equal to 2sigma(1)] was determined, and confirmed the (E) configuration. 2002 Elsevier Science B.V. All rights reserved.