N-isobutylmethanesulfonamide | 133171-80-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-isobutylmethanesulfonamide
• 英文别名: N-(2-methylpropyl)methanesulfonamide
• CAS: 133171-80-9
• 化学式: C₅H₁₃NO₂S
• mdl: MFCD01212950
• 分子量: 151.23
• InChiKey: XBGDRQUFMJRVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  9-(环氧-2-甲基)-9H-咔唑 、 N-isobutylmethanesulfonamide 在 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 生成 N-(3-(9H-carbazol-9-yl)-2-hydroxypropyl)-N-isobutylmethanesulfonamide
  参考文献：
  名称：

  Carbazole-containing sulfonamides and sulfamides: Discovery of cryptochrome modulators as antidiabetic agents

  摘要：

  A series of novel carbazole-containing sulfonamides and sulfamides were synthesized. A structure-activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the results of efficacy studies in diet-induced obese (DIO) mice, and the desired pharmacokinetic parameters, compound 41 was selected for further profiling. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.102
• 作为产物：
  描述：

  异丁胺 、 二甲基亚砜 在 potassium iodide 作用下， 反应 8.0h， 以78%的产率得到N-isobutylmethanesulfonamide
  参考文献：
  名称：

  Electrosynthesis of sulfonamides from DMSO and amines under mild conditions

  摘要：

  在室温下，以DMSO为溶剂，使用带有-SO₂Me基团的前体，开发了一种新的电化学氧化和胺化反应，用于合成磺酰胺。

  DOI：

  10.1039/d1cc00026h

文献信息

• Metal-Free Reductive Cleavage of CN and SN Bonds by Photoactivated Electron Transfer from a Neutral Organic Donor
  作者：Steven O'Sullivan、Eswararao Doni、Tell Tuttle、John A. Murphy

  DOI：10.1002/anie.201306543

  日期：2014.1.7

  A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a) ArCNR and b) ArNC bonds. This study also highlights the assistance given to these cleavage reactions by the groups attached to N in (a) and to C in (b), by lowering LUMO energies and by stabilizing the products of fragmentation.

  光活化的中性有机超电子供体在室温下裂解衍生自二烷基胺的具有挑战性的芳烃磺酰胺。它还裂解 a) ArC  NR 和 b) ArN  C 键。该研究还强调了通过降低 LUMO 能量和稳定碎裂产物，连接到 (a) 中的 N 和连接到 (b) 中的 C 的基团对这些裂解反应的帮助。
• From Ynamides to Highly Substituted Benzo[<i>b</i>]furans: Gold(I)-Catalyzed 5<i>-endo-dig</i>-Cyclization/Rearrangement of Alkylic Oxonium Intermediates
  作者：Maria Camila Blanco Jaimes、Vanessa Weingand、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/chem.201301595

  日期：2013.9.9

  A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross‐coupling/amidation sequence. The gold‐catalyzed conversion of these substrates combined both CO and CC formation steps, thus providing benzofurans with amine functionalities at the 2‐position and alkyl groups at the 3‐position. Cross‐over experiments showed that the

  通过较短的烷基化/交叉偶联/酰胺化顺序，制备了一系列在芳基邻位具有烷氧基的芳基酰胺。这些底物的金催化转化结合了CO和CC的形成步骤，从而使苯并呋喃在2位具有胺官能度，在3位具有烷基官能度。交叉实验表明，烷基迁移步骤是一个分子间过程。对两种产品的X射线晶体结构分析支持了我们的结构任务。在某些情况下，获得了在3位无烷基的相应苯并呋喃作为副产物，这些副产物是通过竞争性的原型脱氢过程形成的。
• Carbazole-containing sulfonamides and sulfamides: Discovery of cryptochrome modulators as antidiabetic agents
  作者：Paul S. Humphries、Ross Bersot、John Kincaid、Eric Mabery、Kerryn McCluskie、Timothy Park、Travis Renner、Erin Riegler、Tod Steinfeld、Eric D. Turtle、Zhi-Liang Wei、Erik Willis

  DOI：10.1016/j.bmcl.2015.12.102

  日期：2016.2

  A series of novel carbazole-containing sulfonamides and sulfamides were synthesized. A structure-activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the results of efficacy studies in diet-induced obese (DIO) mice, and the desired pharmacokinetic parameters, compound 41 was selected for further profiling. (C) 2015 Elsevier Ltd. All rights reserved.
• Electrosynthesis of sulfonamides from DMSO and amines under mild conditions
  作者：Zhiguan Lin、Liangbin Huang、Gaoqing Yuan

  DOI：10.1039/d1cc00026h

  日期：——

  With DMSO as the solvent and the precursor of a –SO₂Me unit at room temperature, a novel electrochemical oxidization and amination of DMSO with amines was developed for the synthesis of sulfonamides.

  在室温下，以DMSO为溶剂，使用带有-SO₂Me基团的前体，开发了一种新的电化学氧化和胺化反应，用于合成磺酰胺。