4-iodo-N-(pivaloyloxy)benzamide | 1268451-44-0

• 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: 4-iodo-N-(pivaloyloxy)benzamide
• 英文别名: [(4-Iodobenzoyl)amino] 2,2-dimethylpropanoate
• CAS: 1268451-44-0
• 化学式: C₁₂H₁₄INO₃
• 分子量: 347.153
• InChiKey: YOTVCMXOHDAMSO-UHFFFAOYSA-N

物化性质

• 密度：
  1.567±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  烯丙氧基苯硫酚 、 4-iodo-N-(pivaloyloxy)benzamide 在 tris(triphenylphosphine)ruthenium(II) chloride 、 苯甲羟肟酸 、 silver(I) acetate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以67%的产率得到N-allyl-4-iodo-N-(phenylthio)benzamide
  参考文献：
  名称：

  钌（II）催化的N-酰氧基酰胺的硝基转移反应合成磺酰亚胺和N-烯丙基-N-（硫代）酰胺

  摘要：

  所述N- acyloxyamides被用作有效N-市售的Ru（II）配合物，从该多种sulfimides被有效地和温和地合成的催化下酰基氮烯的前体在反应与硫醚。如果在硫醚前体中包含烯丙基，则硫酰亚胺的[2,3]-σ重排同时发生，最终获得N-烯丙基-N-（硫代）酰胺。初步的机理研究表明，钌-类胡萝卜素物质应该是转化的关键中间体。

  DOI：

  10.1021/acs.orglett.0c04043
• 作为产物：
  描述：

  对碘苯甲酸乙酯 在 盐酸羟胺 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 4-iodo-N-(pivaloyloxy)benzamide
  参考文献：
  名称：

  Rh(III)-Catalyzed Directed C−H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile

  摘要：

  An efficient Rh(III)-catalyzed oxidative olefination by directed C-H bond activation of N-methoxybenzamides is reported. In this mild, practical, selective, and high-yielding process, the N-O bond acts as an internal oxidant. In addition, simply changing the substituent of the directing/oxidizing group results in the selective formation of valuable tetrahydroisoquinolinone products.

  DOI：

  10.1021/ja109676d

文献信息

• Rhodium(III)-Catalyzed C–H Activation/Annulation with Vinyl Esters as an Acetylene Equivalent
  作者：Nicola J. Webb、Stephen P. Marsden、Steven A. Raw

  DOI：10.1021/ol502095z

  日期：2014.9.19

  The behavior of electron-rich alkenes in rhodium-catalyzed C–H activation/annulation reactions is investigated. Vinyl acetate emerges as a convenient acetylene equivalent, facilitating the synthesis of sixteen 3,4-unsubstituted isoquinolones, as well as select heteroaryl-fused pyridones. The complementary regiochemical preferences of enol ethers versus enol esters/enamides is discussed.

  研究了富电子烯烃在铑催化的CH活化/环化反应中的行为。乙酸乙烯酯以便利的乙炔当量出现，促进了16种3,4-未取代的异喹诺酮以及某些杂芳基稠合的吡啶酮的合成。讨论了烯醇醚相对于烯醇酯/烯酰胺的互补区域化学偏好。
• Csp–Csp³ Bond Formation via Iron(III)-Promoted Hydroalkynylation of Unactivated Alkenes
  作者：Yangyong Shen、Bo Huang、Jing Zheng、Chen Lin、Yu Liu、Sunliang Cui

  DOI：10.1021/acs.orglett.7b00499

  日期：2017.4.7

  An iron(III)-promoted hydroalkynylation of unactivated alkenes toward Csp–Csp3 bond formation has been developed. Various alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified alkynes in this chemoselective protocol. Additionally, the scalability was unraveled and the further divergent transformations of products were conducted to demonstrate

  已开发出铁（III）促进未活化烯烃向Csp–Csp 3键形成的加氢烷基化反应。在这种化学选择性方案中，各种烯烃，包括单，二和三取代的烯烃，都可以平稳地转化为结构多样化的炔烃。此外，还没有对可扩展性进行说明，并且对产品进行了进一步多样化的转换以证明其综合实用性。
• Rhodium(III)-Catalyzed Controllable C−H Bond Functionalization of Benzamides and Vinylidenecyclopropanes: A Directing Group Determined Reaction Pathway
  作者：Cheng Ji、Qin Xu、Min Shi

  DOI：10.1002/adsc.201601308

  日期：2017.3.20

  A controllable rhodium(III)‐catalyzed C−H bond activation of benzamides and vinylidenecyclopropanes (VDCPs) by changing the directing group from C(O)NH–OPiv to C(O)NH–OBoc has been disclosed, affording two different major products in good yields under mild condition, respectively. The substrate scope has been investigated and a plausible reaction mechanism has been also proposed on the basis of previous

  通过将导向基团从C（O）NH-OPiv更改为C（O）NH-OBoc，可控制的铑（III）催化苯甲酰胺和亚乙烯基环丙烷（VDCPs）的C-H键活化，提供了两种不同的主要产物在温和条件下的单产较高。在以前的文献的基础上，研究了底物范围，并提出了合理的反应机理。
• Synthesis of trisubstituted 1,3-oxazin-6-ones via base-catalyzed ring-opening annulation of cyclopropenones with N-(pivaloyloxy)amides
  作者：Takanori Matsuda、Kentaro Yamanaka、Yuki Tabata、Takahiro Shiomi

  DOI：10.1016/j.tetlet.2018.02.084

  日期：2018.4

  azalactone structure. In the presence of catalytic K2CO3 at 60 °C in THF, the disubstituted cyclopropenone couples with benzamides, acrylamides, and a phenylacetamide to produce 2,4,5-trisubstituted 1,3-oxazin-6-ones in 23–99% yield.

  报道了环丙烯酮和N-（新戊酰氧基）酰胺之间的碱催化的[3 + 3]型环。将1,3-N，O-偶极形式正式插入环丙烯酮C C键会产生六元氮杂内酯结构。在60°C的THF中存在催化性K 2 CO 3的情况下，双取代的环丙烯酮与苯甲酰胺，丙烯酰胺和苯乙酰胺偶合，可在23–99中产生2,4,5-三取代的1,3-恶嗪-6-酮。 ％ 屈服。
• Rh(iii)-catalyzed C–H activation/[4 + 3] cycloaddition of benzamides and vinylcarbenoids: facile synthesis of azepinones
  作者：Sunliang Cui、Yan Zhang、Dahai Wang、Qifan Wu

  DOI：10.1039/c3sc51777b

  日期：——

  Vinylcarbenoids are used as three-carbon components in Rh(III)-catalyzed C–H activation/[4 + 3] cycloaddition with benzamides to access azepinones. This transformation makes a feature of simple starting materials, mild reaction conditions and high efficiency. A kinetic isotope effect study was conducted and a plausible mechanism is proposed.

  在 Rh(III)-catalyzed CâH activation/[4 + 3] cycloaddition with benzamides（Rh(III)催化的 CâH 活化/[4 + 3]环加成）反应中，乙烯基烯烃被用作三碳组分，从而获得氮杂环庚酮。这种转化具有起始材料简单、反应条件温和和效率高等特点。研究人员进行了动力学同位素效应研究，并提出了一个合理的机理。