(2,6-dioxo-4-methylcyclohexyl)phenyliodonium inner salt | 86396-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,6-dioxo-4-methylcyclohexyl)phenyliodonium inner salt
• 英文别名: 5-methyl-2-(phenyl-λ³-iodaneylidene)cyclohexane-1,3-dione；(4-methyl-2,6-dioxocyclohexyl)(phenyl)iodonium；5-Methyl-2-(phenyl-lambda3-iodanylidene)cyclohexane-1,3-dione；5-methyl-2-(phenyl-λ3-iodanylidene)cyclohexane-1,3-dione
• CAS: 86396-03-4
• 化学式: C₁₃H₁₃IO₂
• 分子量: 328.15
• InChiKey: VJFLESCLVISNQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,6-dioxo-4-methylcyclohexyl)phenyliodonium inner salt 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到5-Methylcyclohexane-1,2,3-trione
  参考文献：
  名称：

  Ozonolytic Fragmentation of Phenyliodonium β-Diketonates; A Convenient Synthesis of Unsolvatedvic-Triketones

  摘要：

  DOI：

  10.1055/s-1983-30350
• 作为产物：
  描述：

  碘苯二乙酸 在 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2,6-dioxo-4-methylcyclohexyl)phenyliodonium inner salt
  参考文献：
  名称：

  Study on anti-proliferative effect of benzoxathiole derivatives through inactivation of NF-κB in human cancer cells

  摘要：

  To investigate the anti-proliferative effect of a newly discovered NF-kB inhibitor, 6,6-dimethyl-2-(phenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one (1a), a series of its analogs (1b-n) were prepared and evaluated for their NF-kappa B inhibition and anti-proliferative activity against various human cancer cell lines. Slight variation of hydrophobicity by replacement of dimethyl group of 1a at 6-position with bulky isopropyl group and introduction of para-fluoro substitution on 2-phenyl group showed good NF-kappa B inhibitory activity and anti-proliferative activity. However, excessive increase in hydrophobicity with 2,4,6-trichloro substituents on phenyl group resulted in the loss of both the activities. From the SAR results, 2-phenylimino-6,7-dihydrobenzo[d][1,3] oxathiol-4(5H)-one was identified as the lead scaffold for investigating new anticancer agent through inactivation of NF-kappa B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.001

文献信息

• Rhodium(II)-Catalyzed Reaction of Iodonium Ylides with Conjugated Compounds: Efficient Synthesis of Dihydrofurans, Oxazoles, and Dihydrooxepines
  作者：Yong Lee、Sang Yoon、Youngwan Seo、Bong Kim

  DOI：10.1055/s-2004-831257

  日期：——

  The rhodium(II)-catalyzed reaction of iodonium ylides with a variety of conjugated compounds has been examined. With α,β-unsaturated esters and α,β-unsaturated ketones, dihydrofurans were produced in moderate yields. Reactions with acrylonitriles yield oxazoles and dihydrofurans in moderate yields, whereas reactions with 1,3-butadienes result in dihydrofurans and dihydrooxepines in good yields, respectively

  已经检查了碘鎓叶立德与各种共轭化合物的铑 (II) 催化反应。使用 α,β-不饱和酯和 α,β-不饱和酮，以中等收率生产二氢呋喃。与丙烯腈反应以中等收率产生恶唑和二氢呋喃，而与 1,3-丁二烯反应分别以良好收率产生二氢呋喃和二氢氧杂环庚烷。形成这些产物的机理途径已根据环丙烷中间体或 1,3-偶极环加成机理进行了描述。
• Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C–H Activation
  作者：Yuqin Jiang、Pengfei Li、Jie Zhao、Bingxian Liu、Xingwei Li

  DOI：10.1021/acs.orglett.0c02618

  日期：2020.10.2

  The rhodium(III)-catalyzed coupling of C–H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C–H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol

  铑（III）催化的C–H底物与碘鎓碘化物的偶联已经实现了各种环状骨架的有效合成，其中碘鎓碘化物已被认为是有效且出色的卡宾前体。该反应系统适用于在轻度和氧化还原中性条件下的sp 2和sp 3 C–H底物。在克规模的反应中，催化剂的负载量可以低至0.5mol％。代表性产品在纳摩尔水平下对人癌细胞具有细胞毒性。
• Rhodium(<scp>iii</scp>)-catalyzed cascade C–H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines
  作者：Lu Chen、Zhichao Wang、Yangyang Wang、Liqiang Hao、Xiaobo Xu、Gaorong Wu、Yafei Ji

  DOI：10.1039/d1ob02110a

  日期：——

  A highly efficient Rh(III)-catalyzed cascade C–H activation/annulation of sulfoximines with iodonium ylides under metal-oxidant-free conditions has been reported. The fused cyclohexanone-1,2-benzothiazine scaffold is readily achieved with a one-pot process in this reaction. This protocol exhibits good functional group tolerance and moderate to excellent yields. Additionally, the olefination of the

  已经报道了在无金属氧化剂的条件下，一种高效的 Rh( III ) 催化的级联 C-H 活化/环化亚砜亚胺与碘鎓叶立德。在该反应中，通过一锅法很容易实现融合的 cyclohexanone-1,2-benzothiazine 支架。该协议表现出良好的官能团耐受性和中等至优异的产量。此外，目标产物的烯烃化说明了该策略的前景广阔。
• Rh(<scp>iii</scp>)-Catalyzed C(sp²)–H functionalization/cyclization cascade of <i>N</i>-carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives
  作者：Zhi-Peng Han、Meng-Meng Xu、Rui-Ying Zhang、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1039/d1gc01820e

  日期：——

  A rhodium-catalyzed synthesis of indoloquinazolinone from a readily available hypervalent iodonium reagent and N-carboxamide indole was developed. The protocol features broad functional group tolerance, mild conditions, and excellent yields. The target products were obtained simply by filtration, without tedious column chromatography. Notably, the noble metal catalyst system can be recycled effectively

  开发了铑催化合成吲哚喹唑啉酮从容易获得的高价碘试剂和N-羧酰胺吲哚。该协议具有广泛的官能团耐受性、温和的条件和优异的产量。无需繁琐的柱层析，只需过滤即可获得目标产物。值得注意的是，贵金属催化剂体系至少可以有效回收十次。该策略可能适用于工业生产。
• Rh( <scp>III</scp> )‐Catalyzed Diverse C—H Functionalization of Iminopyridinium Ylides
  作者：Zhenzhen Dong、Pengfei Li、Xingwei Li、Bingxian Liu

  DOI：10.1002/cjoc.202100203

  日期：2021.9

  Divergent synthesis of useful skeletons has been realized via rhodium(III)-catalyzed C—H activation of iminopyridinium ylides and coupling with various unsaturated coupling reagents. Isocoumarins and isoquinolones were obtained via cleavage of the C—N or N—N bond in the ylidic directing group, while fluorinated alkenes were delivered with the directing group intact. The reactions occurred with wide

  通过铑（III）催化的亚氨基吡啶鎓叶立德的CH活化并与各种不饱和偶联剂偶联，已经实现了有用骨架的发散合成。异香豆素和异喹诺酮获得经由所述C-N或N-N键的ylidic导向基团中的裂解，而氟化烯烃用的导向基团完整递送。该反应在氧化还原中性和耐空气条件下以广泛的底物范围和良好的效率发生。代表性产品表现出固态荧光特性和对人类癌细胞的抑制生物活性。