4-甲氧基-N-(4-甲氧苄基)苯磺酰胺 | 122134-66-1

• 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: 4-甲氧基-N-(4-甲氧苄基)苯磺酰胺
• 英文名称: 4-methoxy-N-(4-methoxybenzyl)benzenesulfonamide
• 英文别名: 4-methoxy-N-[(4-methoxyphenyl)methyl]benzenesulfonamide
• CAS: 122134-66-1
• 化学式: C₁₅H₁₇NO₄S
• mdl: MFCD00694474
• 分子量: 307.37
• InChiKey: VADICDMNVKEEAM-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  476.6±55.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲氧基-N-(4-甲氧苄基)苯磺酰胺 在 盐酸羟胺 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-[(4-methoxyphenyl)methyl(4-methoxyphenyl)sulfonylamino]ethanehydroxamic acid
  参考文献：
  名称：

  Discovery of CGS 27023A, a Non-Peptidic, Potent, and Orally Active Stromelysin Inhibitor That Blocks Cartilage Degradation in Rabbits

  摘要：

  Structure-activity relationships of a lead hydroxamic acid inhibitor of recombinant human stromelysin were systematically defined by taking advantage of a concise synthesis that allowed diverse functionality to be explored at each position in a template. An ex vivo rat model and an in vivo rabbit model of stromelysin-induced cartilage degradation were used to further optimize these analogs for oral activity and duration of action. The culmination of these modifications resulted in CGS 27023A, a potent, orally active stromelysin inhibitor that blocks the erosion of cartilage matrix.

  DOI：

  10.1021/jm960871c
• 作为产物：
  描述：

  4,4'-二甲氧基二苯二硫 在 1,3-二氯-5,5-二甲基海因 、 水 、 苄基三甲基氯化铵 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 4-甲氧基-N-(4-甲氧苄基)苯磺酰胺
  参考文献：
  名称：

  使用 1,3-二氯-5,5-二甲基乙内酰脲 (DCH) 从硫醇和二硫化物方便地一锅法合成磺胺

  摘要：

  描述了从硫醇和二硫化物方便合成磺胺类药物。从硫醇原位制备磺酰氯是通过在 N苄基-三甲基氯化铵和水下用 1,3-二氯-5,5-二甲基乙内酰脲 (DCH) 氧化来完成的。然后进一步使磺酰氯在同一反应容器中与过量胺反应。

  DOI：

  10.5012/bkcs.2012.33.2.383

文献信息

• One-Pot Synthesis of Sulfonamides and Sulfonyl Azides from Thiols using Chloramine-T
  作者：Behrooz Maleki、Saba Hemmati、Reza Tayebee、Sirous Salemi、Yasaman Farokhzad、Mehdi Baghayeri、Farrokhzad Mohammadi Zonoz、Elahe Akbarzadeh、Rohollah Moradi、Azam Entezari、Mohammad Reza Abdi、Samaneh Sedigh Ashrafi、Fereshteh Taimazi、Majid Hashemi

  DOI：10.1002/hlca.201200648

  日期：2013.11

  A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine‐T (=N‐chlorotosylamide=N‐chloro‐4‐methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.

  描述了由硫醇方便地合成磺酰胺和磺酰叠氮化物。通过用氯胺-T（= N-氯代甲苯磺酰胺= N-氯--4-甲基苯磺酰胺），四丁基氯化铵（Bu 4 NCl）和H 2 O氧化，可以完成从硫醇中磺酰氯的原位制备。在同一锅中与过量的胺或NaN 3反应。
• Convenient One-Pot Synthesis of Sulfonamides and Sulfonyl Azides from Thiols Using N-Chlorosuccinimide
  作者：Hojat Veisi、Ramin Ghorbani-Vaghei、Saba Hemmati、Jafar Mahmoodi

  DOI：10.1055/s-0030-1261232

  日期：2011.10

  A convenient synthesis of sulfonamidesand sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel.

  描述了从硫醇中方便地合成磺酰胺和磺酰叠氮化物。从硫醇原位制备磺酰氯是通过用 N-氯琥珀酰亚胺 (NCS)、四丁基氯化铵和水氧化来完成的。然后使磺酰氯在同一反应容器中进一步与过量的胺或叠氮化钠反应。
• Convenient One‐Pot Synthesis of Sulfonamides from Thiols using Trichloroisocyanuric Acid
  作者：Jason D. Bonk、David T. Amos、Sarah J. Olson

  DOI：10.1080/00397910701356942

  日期：2007.6

  Abstract A convenient synthesis of sulfonamides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), benzyltrimethylammonium chloride and water (2.5 equiv). The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel. Triethylamine can be optionally added as acid

  摘要 描述了一种从硫醇中方便地合成磺酰胺的方法。从硫醇原位制备磺酰氯是通过用三氯异氰尿酸 (TCCA)、苄基三甲基氯化铵和水（2.5 当量）氧化来完成的。然后使磺酰氯在同一反应容器中进一步与过量的胺反应。可以任选地加入三乙胺作为酸清除剂。
• Synthesis of N-Sulfonyl Ynamido-Phosphonates: Valuable Partners for Cycloadditions
  作者：Vincent Perez、Antoine Fadel、Nicolas Rabasso

  DOI：10.1055/s-0036-1589042

  日期：2017.9

  Abstract N-Sulfonyl ynamido-phosphonates were prepared from sulfonamides and bromo alkynylphosphonates through a direct copper-catalyzed coupling reaction. The substrates were obtained in good to excellent yields. The latter are valuable partners to react with nitrile-oxides­ to form isoxazoles in good yields and with an exclusive regio­selectivity. N-Sulfonyl ynamido-phosphonates were prepared from

  摘要 通过直接的铜催化的偶联反应，由磺酰胺和溴代炔基膦酸酯制备N-磺酰基ynamido-膦酸酯。以良好至优异的产率获得基材。后者是有价值的合作伙伴，可与腈氧化物反应，以高收率和独特的区域选择性形成异恶唑。 通过直接的铜催化的偶联反应，由磺酰胺和溴代炔基膦酸酯制备N-磺酰基ynamido-膦酸酯。以良好至优异的产率获得基材。后者是有价值的合作伙伴，可与腈氧化物反应，以高收率和独特的区域选择性形成异恶唑。
• Synthesis and Cross-Coupling of Sulfonamidomethyltrifluoroborates
  作者：Gary A. Molander、Nicolas Fleury-Brégeot、Marie-Aude Hiebel

  DOI：10.1021/ol200202g

  日期：2011.4.1

  Sulfonamidomethyltrifluoroborates were successfully synthesized and cross-coupled with a wide range of aryl and heteroaryl chlorides, allowing the construction of a sulfonamidomethyl aryl linkage through a new disconnection, thus offering a new way to access such structurally interesting motifs.