N,N-diethylnaphthalene-1-sulfonamide | 501411-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diethylnaphthalene-1-sulfonamide
• 英文别名: diethyl-1-naphthalenesulfonamide
• CAS: 501411-81-0
• 化学式: C₁₄H₁₇NO₂S
• mdl: MFCD16171835
• 分子量: 263.36
• InChiKey: FDTQVUQNEIOCPP-UHFFFAOYSA-N

物化性质

• 熔点：
  61-71 °C(Solv: hexane (110-54-3))
• 沸点：
  411.5±28.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethylnaphthalene-1-sulfonamide 在 正丁基锂 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 13.0h， 生成 N,N-diethyl-2-(4-methoxyphenyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Directed ortho-Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides

  摘要：

  A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 -> 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryis and heteroblaryls, 3 -> 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.

  DOI：

  10.1021/ol201175g
• 作为产物：
  描述：

  1-碘萘 在 四(三苯基膦)钯 、 磺酰氯 、 potassium nitrate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 N,N-diethylnaphthalene-1-sulfonamide
  参考文献：
  名称：

  芳族和脂肪族三异丙基甲硅烷基硫烷基被氧化为磺酰氯：磺酰胺的制备

  摘要：

  制备了一系列芳族和脂族三异丙基硅烷基硫烷基，并用KNO 3 / SO 2 Cl 2氧化为磺酰氯。磺酰氯通过转化为磺酰胺来表征。

  DOI：

  10.1016/j.tetlet.2003.08.073

文献信息

• I₂/TBHP Mediated C–N and C–H Bond Cleavage of Tertiary Amines toward Selective Synthesis of Sulfonamides and β-Arylsulfonyl Enamines: The Solvent Effect on Reaction
  作者：Junyi Lai、Liming Chang、Gaoqing Yuan

  DOI：10.1021/acs.orglett.6b01412

  日期：2016.7.1

  A novel method toward synthesis of sulfonamides and β-arylsulfonyl enamines has been developed via I2/TBHP mediated C–N and C–H bond cleavage of tertiary amines, which features highly selective formation of two different target products depending on the reaction solvent. The experimental results reveal that H2O as the solvent could effectively achieve the C–N bond cleavage to produce sulfonamides due

  通过I 2 / TBHP介导的叔胺的C–N和C–H键裂解，已经开发了一种合成磺酰胺和β-芳基磺酰基烯胺的新方法，该方法具有高选择性地形成两种不同目标产物的特点，具体取决于反应溶剂。实验结果表明，由于H 2 O参与了H 2 O双重作用的反应过程，因此H 2 O作为溶剂可以有效地实现C–N键的裂解，生成磺酰胺。与H 2 O不同，有机溶剂（例如二甲基亚砜）可以促进叔胺的C–H键裂解，从而生成β-芳基磺酰基烯胺。
• METHOD OF INHIBITING APOLIPOPROTEIN-E EXPRESSION WHILE INCREASING EXPRESSION OF AT LEAST ONE OF LDL-RECEPTOR PROTEIN OR ABCA1 PROTEIN COMPRISING ADMINISTERING A SMALL COMPOUND
  申请人：California State University, Fresno

  公开号：US20180093960A1

  公开（公告）日：2018-04-05

  This invention offers an effective method of decreasing expression of apolipoprotein E and increasing expression of at least one of either LDL-receptor protein or AbcA1 protein including selecting mammalian cells expressing apoE and at least one of either LDL-receptor protein or AbcA1 protein, contacting the mammalian cell with an effective amount of a compound having general formula (I) or general formula (II) in an amount sufficient to decrease expression of the apoE and increase expression of at least one of the LDL-receptor protein or the AbcA1 protein in the mammalian cell.

  这项发明提供了一种有效的方法，可以降低载脂蛋白E的表达，并增加至少一种LDL受体蛋白或AbcA1蛋白的表达，包括选择表达apoE和至少一种LDL受体蛋白或AbcA1蛋白的哺乳动物细胞，将哺乳动物细胞与通式（I）或通式（II）的化合物的有效量接触，其量足以降低apoE的表达并增加哺乳动物细胞中至少一种LDL受体蛋白或AbcA1蛋白的表达。
• Catalytic Arylation of Sulfamoyl Chlorides: A Practical Synthesis of Sulfonamides
  作者：Christopher G. Frost、Joseph P. Hartley、David Griffin

  DOI：10.1055/s-2002-34907

  日期：——

  Commercially available indium(III) triflate is shown to be an efficient catalyst for the sulfamoylation of aromatics.

  市售的三氟甲磺酸铟 (III) 被证明是芳烃氨磺酰化的有效催化剂。
• Ink composition containing a photo-acid and a photo-base generator and processes using them
  申请人：FUJIFILM Corporation

  公开号：EP1702962B1

  公开（公告）日：2008-12-24
• Directed <i>ortho</i>-Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides
  作者：Cédric Schneider、Ellen Broda、Victor Snieckus

  DOI：10.1021/ol201175g

  日期：2011.7.15

  A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 -> 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryis and heteroblaryls, 3 -> 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.