3-(4-bromophenyl)-1,2-benzoisothiazole 1,1-dioxide | 1345021-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(4-bromophenyl)-1,2-benzoisothiazole 1,1-dioxide
• 英文别名: 3-(4-Bromophenyl)-1,2-benzothiazole 1,1-dioxide
• CAS: 1345021-05-7
• 化学式: C₁₃H₈BrNO₂S
• 分子量: 322.182
• InChiKey: SLIIHOSZVREFRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-1,2-benzoisothiazole 1,1-dioxide 在 三(五氟苯基)硼烷 、 甲基苯基硅烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以96%的产率得到3-(4-bromophenyl)-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide
  参考文献：
  名称：

  B（C6F5）3催化的环状N-磺酰基酮亚胺还原

  摘要：

  开发了一种无金属的方法，在温和的条件下，使用市售的甲基苯基硅烷作为还原剂，还原由B（C 6 F 5）3催化的环状N-磺酰基酮亚胺。这种还原方法是有效的，不仅可以提供预期的环状N-磺酰胺类化合物，而且产率很高，而且显示出良好的官能团耐受性。

  DOI：

  10.1002/ejoc.201900706
• 作为产物：
  描述：

  (4-bromophenyl)magnesium bromide 、 糖精 以 四氢呋喃 为溶剂， 反应 3.0h， 以65%的产率得到3-(4-bromophenyl)-1,2-benzoisothiazole 1,1-dioxide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of benzo[1.3.2]dithiazolium ylide 1,1-dioxide derivatives as potential dual cyclooxygenase-2/5-lipoxygenase inhibitors

  摘要：

  3-(4-Bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide (5) was discovered as a new prototype for dual inhibitors of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX). Thus, the structure-activity relationships of benzo[1.3.2]dithiazolium ylide 1,1-dioxide skeleton were carried out. The 6-NO2 group played an essential role in the inhibitory activity. In addition, moderate-sized lipophilic substituents at the para-position of the 3-aryl moiety were required for dual COX-2/5-LOX inhibitory activity. Among the identified potent dual inhibitors, 3-(4-tbutylphenyl) derivative 30c (IC50 values of 0.27 mu M and 0.30 mu M against COX-2 and 5-LOX, respectively) and 3-(4-biphenyl) derivative 30f (IC50 values of 0.50 mu M and 0.15 mu M against COX-2 and 5-LOX, respectively) were the most potent dual COX-2/5-LOX inhibitors. Intraperitoneal administration of 30c at 100 mg/kg demonstrated potent acute anti-inflammatory activity. As a result, benzo[1.3.2]dithiazolium ylide 1,1-dioxide represented a novel scaffold for the exploitation in developing dual COX-2/5-LOX inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.003

文献信息

• Enantioselective organocatalytic oxidation of ketimine
  作者：Shinobu Takizawa、Kenta Kishi、Mohamed Ahmed Abozeid、Kenichi Murai、Hiromichi Fujioka、Hiroaki Sasai

  DOI：10.1039/c5ob02042e

  日期：——

  with promoted the enantioselective organocatalytic oxidation of to afford oxaziridines bearing a tetrasubstituted carbon stereogenic center in high yields with up to 87% ee.

  使用和促进了的对映选择性有机催化氧化，产生了含有四次取代碳手性中心的氧杂环丙烷，收率高达87% ee。
• Phosphane-Catalyzed [4+2] Annulation of Allenoates with Ketimines: Synthesis of Sultam-Fused Tetrahydropyridines
  作者：Xiang-Yu Chen、Song Ye

  DOI：10.1002/ejoc.201200747

  日期：2012.10

  Cyclic ketimines were successfully used as electrophiles in phosphane-catalyzed [4+2] annulation reactions with ethyl 2-methyl-2,3-butadienoate to give the corresponding highly substituted tetrahydropyridine derivatives in moderate to good yields (55–73 %), and with moderate to excellent regioselectivity.

  环状酮亚胺成功地用作磷烷催化的 [4+2] 环化反应中的亲电子试剂，与 2-甲基-2,3-丁二烯酸乙酯以中等至良好的产率（55-73%）得到相应的高度取代的四氢吡啶衍生物，并且具有中等至优异的区域选择性。
• Catalytic [2+2] and [3+2] cycloaddition reactions of allenoates with cyclic ketimines
  作者：Xiang-Yu Chen、Ruo-Chen Lin、Song Ye

  DOI：10.1039/c2cc16055b

  日期：——

  Cyclic ketimines as electrophiles for [2+2] and [3+2] cycloaddition reactions of allenoates have been developed, affording functionalized sultam-fused azetidines and dihydropyrroles, respectively, in good yields with high regioselectivities.

  已经开发出环状酮亚胺作为联烯酸酯的[2+2]和[3+2]环加成反应的亲电试剂，分别以良好的收率和高区域选择性提供功能化的磺内酰胺稠合氮杂环丁烷和二氢吡咯。
• Rh(<scp>iii</scp>)-catalyzed sequential spiroannulation/lactonization of 3-aryl <i>N</i>-sulfonyl ketimines with 4-hydroxy-2-alkynoates by C–H bond activation
  作者：S. Prashanth、Chidrawar Ajay、Kommu Nagesh、B. Sridhar、B. V. Subba Reddy

  DOI：10.1039/d3nj04312f

  日期：2024.4.29

  been developed for the synthesis of a highly rigid spirobenzosultam lactones in good yields with high regioselectivity by means of aromatic ortho-C–H bond activation/functionalization of 3-aryl N-sulfonyl ketimines with 4-hydroxy-2-alkynoates. The reaction proceeds through a cascade of C–H activation followed by spiroannulation and lactonization. In this approach, two C–C and C–O bonds are formed in a

  开发了一种连续铑（III）催化的螺环化和内酯化策略，通过芳香族邻-C-H键活化/3-芳基N-磺酰基的功能化，以高产率和高区域选择性合成高刚性的螺苯磺内酯。酮亚胺与 4-羟基-2-炔酸酯。该反应通过一系列 C-H 活化、随后的螺环化和内酯化进行。在这种方法中，一步形成两个 C-C 和 C-O 键。这是关于环状N-磺酰基酮亚胺与羟基炔酸酯的螺环化的第一份报告。
• Design, synthesis and biological evaluation of benzo[1.3.2]dithiazolium ylide 1,1-dioxide derivatives as potential dual cyclooxygenase-2/5-lipoxygenase inhibitors
  作者：Chen-Ming Tan、Grace Shiahuy Chen、Chien-Shu Chen、Pei-Teh Chang、Ji-Wang Chern

  DOI：10.1016/j.bmc.2011.09.003

  日期：2011.11

  3-(4-Bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide (5) was discovered as a new prototype for dual inhibitors of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX). Thus, the structure-activity relationships of benzo[1.3.2]dithiazolium ylide 1,1-dioxide skeleton were carried out. The 6-NO2 group played an essential role in the inhibitory activity. In addition, moderate-sized lipophilic substituents at the para-position of the 3-aryl moiety were required for dual COX-2/5-LOX inhibitory activity. Among the identified potent dual inhibitors, 3-(4-tbutylphenyl) derivative 30c (IC50 values of 0.27 mu M and 0.30 mu M against COX-2 and 5-LOX, respectively) and 3-(4-biphenyl) derivative 30f (IC50 values of 0.50 mu M and 0.15 mu M against COX-2 and 5-LOX, respectively) were the most potent dual COX-2/5-LOX inhibitors. Intraperitoneal administration of 30c at 100 mg/kg demonstrated potent acute anti-inflammatory activity. As a result, benzo[1.3.2]dithiazolium ylide 1,1-dioxide represented a novel scaffold for the exploitation in developing dual COX-2/5-LOX inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.