N-(4-iodophenyl)-N-methylmethanesulfonamide | 110965-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-iodophenyl)-N-methylmethanesulfonamide
• 英文别名: N-(4-Iodophenyl)-N-methylmethanesulphonamide
• CAS: 110965-10-1
• 化学式: C₈H₁₀INO₂S
• mdl: MFCD25955526
• 分子量: 311.143
• InChiKey: FDRGCSHYAFCRGM-UHFFFAOYSA-N

物化性质

• 沸点：
  366.8±44.0 °C(Predicted)
• 密度：
  1.824±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-(4-iodophenyl)-N-methylmethanesulfonamide 、 2-mercapto-4-[(2S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-thiophene 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-Methyl-N-{4-[4-(2,2,4-trimethyl-[1,3]dioxolan-4-yl)-thiophen-2-ylsulfanyl]-phenyl}-methanesulfonamide
  参考文献：
  名称：

  Chiral Dioxolane Inhibitors of Leukotriene Biosynthesis: Structure-Activity Relationships and Syntheses Using Asymmetric Dihydroxylation

  摘要：

  1,3-Dioxolanes have been described as chiral inhibitors of 5-lipoxygenase (5LO). In the present work, this series has been developed further to provide agents which showed comparable or superior potency in vivo to ZD2138, a methoxytetrahydropyran inhibitor of 5LO, which is currently undergoing clinical evaluation. An asymmetric synthesis was developed to these dioxolanes based on asymmetric dihydroxylation. (S)-N-Methyl-4'-[[4-(2,2,4-trimethyl-1,3 dioxolan-4-yl)thien-2-yl]thio]acetanilid ((S)-10d) inhibited leukotriene B-4 (LTB(4)) synthesis in A23187-stimulated human whole blood in vitro with IC50 0.039 mu M, 25-fold more potent than (R)-10d. In vivo, (S)-10d inhibited LTB(4) synthesis by 70% in zymosan-inflamed air pouch exudate in rat 10 h after an oral dose of 1.5 mg/kg. Structure-activity relationship considerations suggested that the dioxolane and methoxytetrahydropyran series are related, a conclusion which can be supported by molecular modeling.

  DOI：

  10.1021/jm00020a008
• 作为产物：
  描述：

  N-(3-chloro-4-iodophenyl)-N-methylmethanesulphonamide 生成 N-(4-iodophenyl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  Sulphonamide derivatives

  摘要：

  这项发明涉及公式I的磺胺基衍生物，其中R.sup.1包括(1-4C)烷基；R.sup.2和R.sup.3一起形成--A.sup.2--X.sup.2--A.sup.3--，定义具有5到7个环原子的环，其中A.sup.2和A.sup.3各自是(1-3 C)烷基和X.sup.2是氧、硫、亚硫酰基或磺酰基；A.sup.1是直接连接到X.sup.1或是(1-3 C)烷基；X.sup.1是氧、硫、亚硫酰基、磺酰基或亚胺；Ar是可选择取代的苯基或Ar是吡啶基；Q是氮或公式CR.sup.7，其中R.sup.7包括氢、卤素、(1-4 C)烷基和(1-4 C)烷氧基；R.sup.4和R.sup.5中的每一个是(1-4 C)烷基、(3-4 C)烯基、(3-4 C)炔基或可选择取代的苯基、苄基或吡啶基，或R.sup.5可以是氢；而R.sup.6具有R.sup.7定义的任何含义；或其药学上可接受的盐；其制备方法；含有它们的药物组合物以及它们作为5-脂氧合酶抑制剂的用途。

  公开号：

  US05236948A1

文献信息

• Dichloroaniline derivatives
  申请人：Glaxo Group Limited

  公开号：US04943591A1

  公开（公告）日：1990-07-24

  The invention provides compounds of the general formula (I) ##STR1## wherein X represents a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain and Y represents a bond, or a C.sub.1-4 alkylene, C.sub.2-4 alkenylene or C.sub.2-4 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is not more than 8; Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms or the groups C.sub.1-3 alkyl, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, C.sub.1-3 alkoxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom, or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O-- or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NR.sup.3 R.sup.4 group), and q represents an integer from 0 to 3], --NR.sup.5 COR.sup.19 (where R.sup.5 is as defined above and R.sup.19 represents a phenyl group), --(CH.sub.2).sub.r R.sup.7 [where R.sup.7 represents --NR.sup.5 SO.sub.2 R.sup.8 (where R.sup.8 represents a C.sub.1-4 alkyl, phenyl or --NR.sup.3 R.sup.4 group), --NR.sup.5 COCH.sub.2 N(R.sup.5).sub.2 (where each of the groups R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group), --COR.sup.9 (where R.sup.9 represents hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4), --SR.sup.10 (where R.sup.10 is a hydrogen atom, or a C.sub.1-4 alkyl group optionally substituted by hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4), --SOR.sup.10, --SO.sub.2 R.sup.10, --CN, or --NR.sup.11 R.sup.12 (where R.sup.11 and R.sup.12 represent a hydrogen atom or a C.sub.1-4 alkyl group, at least one of which is C.sub.2-4 alkyl substituted by a hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4), and r represents an integer from 0 to 3], --O(CH.sub.2).sub.q COR.sup.9 (where q and R.sup.9 are as defined above), or --O(CH.sub.2).sub.t R.sup.13 [where R.sup.13 represents hydroxy, NR.sup.3 R.sup.4, NR.sup.11 R.sup.12 or a C.sub.1-4 alkoxy group optionally substituted by hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4, and t is an integer 2 or 3], or Ar is a phenyl group substituted by an alkylenedioxy group --O(CH.sub.2).sub.p O-- where p is 1 or 2; R.sup.1 and R.sup.2 each represents a hydrogen atom or a C.sub.1-3 alkyl group, with the proviso that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 4; and physiologically acceptable salts and solvates (e.g. hydrates) thereof. The compounds of formula (I) have a stimulant action at .beta..sub.2 -adrenoreceptors and are useful, in particular, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.

  本发明提供了一般式(I)的化合物：##STR1## 其中，X代表C.sub.1-6烷基，C.sub.2-6烯基或C.sub.2-6炔基链，Y代表键或C.sub.1-4烷基，C.sub.2-4烯基或C.sub.2-4炔基链，但X和Y中碳原子的总和不超过8；Ar代表苯基，可选地由一个或多个取代基选自卤素原子或C.sub.1-3烷基，硝基，--(CH.sub.2).sub.qR [其中R为羟基，C.sub.1-3烷氧基，--NR.sup.3R.sup.4（其中R.sup.3和R.sup.4各代表氢原子或C.sub.1-4烷基，或--NR.sup.3R.sup.4形成有5-7个环成员的饱和杂环氨基，其中环中可选地包含一个或多个原子选自--O--或--S--或--NH--或--N(CH.sub.3)--），--NR.sup.5COR.sup.6（其中R.sup.5代表氢原子或C.sub.1-4烷基，R.sup.6代表氢原子或C.sub.1-4烷基，C.sub.1-4烷氧基或--NR.sup.3R.sup.4基），q代表0至3的整数]，--NR.sup.5COR.sup.19（其中R.sup.5如上定义，R.sup.19代表苯基），--(CH.sub.2).sub.rR.sup.7 [其中R.sup.7代表--NR.sup.5SO.sub.2R.sup.8（其中R.sup.8代表C.sub.1-4烷基，苯基或--NR.sup.3R.sup.4基），--NR.sup.5COCH.sub.2N(R.sup.5).sub.2（其中每个R.sup.5代表氢原子或C.sub.1-4烷基），--COR.sup.9（其中R.sup.9代表羟基，C.sub.1-4烷氧基或NR.sup.3R.sup.4），--SR.sup.10（其中R.sup.10为氢原子或可选地由羟基，C.sub.1-4烷氧基或NR.sup.3R.sup.4取代的C.sub.1-4烷基），--SOR.sup.10，--SO.sub.2R.sup.10，--CN或--NR.sup.11R.sup.12（其中R.sup.11和R.sup.12代表氢原子或C.sub.1-4烷基，至少有一个是由羟基，C.sub.1-4烷氧基或NR.sup.3R.sup.4取代的C.sub.2-4烷基），r代表0至3的整数]，--O(CH.sub.2).sub.qCOR.sup.9（其中q和R.sup.9如上定义），或--O(CH.sub.2).sub.tR.sup.13 [其中R.sup.13代表羟基，NR.sup.3R.sup.4，NR.sup.11R.sup.12或可选地由羟基，C.sub.1-4烷氧基或NR.sup.3R.sup.4取代的C.sub.1-4烷氧基，t为2或3]，或Ar是由烷二氧基基团--O(CH.sub.2).sub.pO-取代的苯基，其中p为1或2；R.sup.1和R.sup.2各代表氢原子或C.sub.1-3烷基，但R.sup.1和R.sup.2中碳原子的总和不超过4；以及其生理上可接受的盐和溶剂（例如水合物）。式(I)的化合物在.beta..sub.2-肾上腺素受体上具有兴奋作用，并且特别适用于治疗与可逆性气道阻塞有关的疾病，如哮喘和慢性支气管炎。
• Dichloroaniline derivatives for the therapy or prophylaxysis of a
  申请人：Glaxo Group Limited

  公开号：US05006556A1

  公开（公告）日：1991-04-09

  The invention provides compounds of the general formula (I) ##STR1## wherein X represents a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain and Y represents a bond, or a C.sub.1-4 alkylene, C.sub.2-4 alkenylene or C.sub.2-4 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is not more than 8; Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms or the groups C.sub.1-3 alkyl, nitro, --(CH.sub.2)qR [where R is hydroxy, C.sub.1-3 alkoxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom, or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O-- or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NR.sup.3 R.sup.4 group), and q represents an integer from 0 to 3], --NR.sup.5 COR.sup.19 (where R.sup.5 is as defined above and R.sup.19 represents a phenyl group), --(CH.sub.2).sub.r R.sup.7 [where R.sup.7 represents --NR.sup.5 SO.sub.2 R.sup.8 (where R.sup.8 represents a C.sub.1-4 alkyl, phenyl or --NR.sup.3 R.sup.4 group), --NR.sup.5 COCH.sub.2 N(R.sup.5).sub.2 (where each of the groups R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group), --COR.sup.9 (where R.sup.9 represents hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4), --SR.sup.10 (where R.sup.10 is a hydrogen atom, or a C.sub.1-4 alkyl group optionally substituted by hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4), --SOR.sup.10, --SO.sub.2 R.sup.10, --CN, or --NR.sup.11 R.sup.12 (where R.sup.11 and R.sup.12 represent a hydrogen atom or a C.sub.1-4 alkyl group, at least one of which is C.sub.2-4 alkyl substituted by a hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4 group), and r represents an integer from 0 to 3], --O(CH.sub.2).sub.q COR.sup.9 (where q and R.sup.9 are as defined above), or --O(CH.sub.2).sub.t R.sup.13 [where R.sup.13 represents hydroxy, NR.sup.3 R.sup.4, NR.sup.11 R.sup.12 or a C.sub.1-4 alkoxy group optionally substituted by hydroxy, C.sub.1-4 alkoxy or NR.sup.3 R.sup.4, and t is an integer 2 or 3], or Ar is a phenyl group substituted by an alkylenedioxy group --O(CH.sub.2).sub.p O-- where p is 1 or 2; R.sup.1 and R.sup.2 each represents a hydrogen atom or a C.sub.1-3 alkyl group, with the proviso that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 4; and physiologically acceptable salts and solvates (e.g. hydrates) thereof. The compounds of formula (I) have a stimulant action at .beta..sub.2 -adrenoreceptors and are useful, in particular, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.

  本发明提供了一般式（I）的化合物：##STR1## 其中X代表C.sub.1-6烷基，C.sub.2-6烯基或C.sub.2-6炔基链，Y代表键或C.sub.1-4烷基，C.sub.2-4烯基或C.sub.2-4炔基链，但X和Y中碳原子的总和不超过8；Ar代表苯基，可选地取代一个或多个取代基，所述取代基选择自卤原子或C.sub.1-3烷基、硝基、--(CH.sub.2)qR [其中R为羟基、C.sub.1-3烷氧基、--NR.sup.3R.sup.4（其中R.sup.3和R.sup.4分别代表氢原子，或C.sub.1-4烷基，或--NR.sup.3R.sup.4形成有5-7个环成员的饱和杂环氨基，可选地在环中包含一个或多个选择自--O--或--S--或--NH--或--N(CH.sub.3)--的原子或基），--NR.sup.5COR.sup.6（其中R.sup.5代表氢原子或C.sub.1-4烷基，R.sup.6代表氢原子或C.sub.1-4烷基、C.sub.1-4烷氧基或--NR.sup.3R.sup.4基），q代表0至3的整数]、--NR.sup.5COR.sup.19（其中R.sup.5如上定义，R.sup.19代表苯基），--(CH.sub.2).sub.rR.sup.7 [其中R.sup.7代表--NR.sup.5SO.sub.2R.sup.8（其中R.sup.8代表C.sub.1-4烷基、苯基或--NR.sup.3R.sup.4基）、--NR.sup.5COCH.sub.2N(R.sup.5).sub.2（其中R.sup.5的每个基代表氢原子或C.sub.1-4烷基）、--COR.sup.9（其中R.sup.9代表羟基、C.sub.1-4烷氧基或NR.sup.3R.sup.4）、--SR.sup.10（其中R.sup.10为氢原子或C.sub.1-4烷基，可选地被羟基、C.sub.1-4烷氧基或NR.sup.3R.sup.4取代）、--SOR.sup.10、--SO.sub.2R.sup.10、--CN或--NR.sup.11R.sup.12（其中R.sup.11和R.sup.12代表氢原子或C.sub.1-4烷基，至少一个基被羟基、C.sub.1-4烷氧基或NR.sup.3R.sup.4取代，且其中至少一个基为C.sub.2-4烷基），r代表0至3的整数]、--O(CH.sub.2).sub.qCOR.sup.9（其中q和R.sup.9如上定义），或--O(CH.sub.2).sub.tR.sup.13 [其中R.sup.13代表羟基、NR.sup.3R.sup.4、NR.sup.11R.sup.12或C.sub.1-4烷氧基，可选地被羟基、C.sub.1-4烷氧基或NR.sup.3R.sup.4取代，t为2或3]，或Ar为取代有烷二氧基基团--O(CH.sub.2).sub.pO-的苯基，其中p为1或2；R.sup.1和R.sup.2各代表氢原子或C.sub.1-3烷基，但R.sup.1和R.sup.2中碳原子的总和不超过4；以及其生理上可接受的盐和溶剂（例如水合物）。式（I）化合物在β.sub.2-肾上腺素受体上具有兴奋作用，特别适用于治疗与可逆气道阻塞相关的疾病，例如哮喘和慢性支气管炎。
• Unlocking the Chain‐Walking Process in Gold Catalysis**
  作者：Vivek W. Bhoyare、Akash G. Tathe、Vincent Gandon、Nitin T. Patil

  DOI：10.1002/anie.202312786

  日期：2023.11.13

  A gold-catalyzed chain-walking process is presented herein by employing a ligand-enabled Au(I)/Au(III) redox catalysis. This process is harnessed to develop a novel gold-catalyzed annulation reaction of alkenes with iodoarenes by leveraging the interplay of chain-walking and π-activation reactivity mode.

  本文通过采用配体启用的 Au(I)/Au(III) 氧化还原催化提出了金催化的链行走过程。利用链行走和 π 激活反应模式的相互作用，利用该过程开发了一种新型金催化烯烃与碘芳烃的环化反应。
• Gold-catalyzed alkenylation and arylation of phosphorothioates
  作者：Urvashi、Sampoorna Mishra、Nitin T. Patil

  DOI：10.1039/d3sc04888h

  日期：——

  Reported herein is the ligand-enabled gold-catalyzed alkenylation and arylation of phosphorothioates using alkenyl and aryl iodides. Mechanistic studies revealed a crucial role of the in situ generated Ag–sulfur complex, which undergoes a facile transmetalation with the Au(III) intermediate, thereby leading to the successful realization of the present reaction. Moreover, for the first time, the alkenylation

  本文报道了使用烯基和芳基碘化物进行配位体金催化的硫代磷酸酯的烯基化和芳基化。机理研究揭示了原位生成的银硫络合物的关键作用，该络合物与Au（ III）中间体进行了轻松的金属转移，从而成功实现了本反应。此外，首次提出了在金氧化还原催化下硒代磷酸酯的烯基化反应。
• Gold‐Catalyzed Arylative Cope Rearrangement
  作者：Bidisha Paroi、Chayanika Pegu、Manoj V. Mane、Nitin T. Patil

  DOI：10.1002/anie.202406936

  日期：2024.8.12

  Reported herein is the arylative Cope rearrangement of 1,6-heptadienes facilitated by ligand-enabled redox gold catalysis. Unlike the classical Cope rearrangement involving 1,5-hexadienes, a cyclization-induced [3,3]-rearrangement of 1,6-heptadienes using the merger of π-activation and cross-coupling reactivity, has been achieved.

  本文报道了由配体驱动的氧化还原金催化促进的 1,6-庚二烯的芳基化 Cope 重排。与涉及 1,5-己二烯的经典 Cope 重排不同，利用 π 激活和交叉偶联反应性的合并，实现了环化诱导的 1,6-庚二烯的 [3,3]-重排。