[bis-(2,2-dichloroacetyloxy)iodo]benzene | 54527-51-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [bis-(2,2-dichloroacetyloxy)iodo]benzene
• 英文别名: di(dichloroacetoxy)iodosobenzene；(bis-dichloroacetoxy-iodanyl)-benzene；(Bis-dichloracetoxy-jodanyl)-benzol
• CAS: 54527-51-4
• 化学式: C₁₀H₇Cl₄IO₄
• 分子量: 459.88
• InChiKey: GBVZFHRFRBRRTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [bis-(2,2-dichloroacetyloxy)iodo]benzene 、 1,3-二噁烷-5-酮,2,2-二甲基-,肟 以 二氯甲烷 为溶剂， 反应 2.75h， 以52%的产率得到dichloroacetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester
  参考文献：
  名称：

  α-Acyloxynitroso dienophiles in [4+2] hetero Diels–Alder cycloadditions: mechanistic insights

  摘要：

  alpha-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a beta-oxygenated moiety led to a domino [4+2] cycloaddition/sigma(N-O) bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the sigma(N-O) bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.065
• 作为产物：
  描述：

  碘苯 、 二氯乙酸 在 oxone||potassium monopersulfate triple salt 作用下， 以 氯仿 为溶剂， 以29 %的产率得到[bis-(2,2-dichloroacetyloxy)iodo]benzene
  参考文献：
  名称：

  缺电子氮杂环中的位点选择性苄基 C–H 羟基化

  摘要：

  苄基 C-H 键可以转化为许多官能团，通常通过涉及氢原子转移作为关键键断裂步骤的机制。抽象物质通常是亲电子自由基，这使得这些反应最适合富电子的 C-H 键，以实现适当的极性匹配。因此，缺电子系统（例如吡啶和嘧啶）相对不活泼，因此在底物范围中代表性不足。在本报告中，我们描述了一种杂苄羟基化的新方法（对于嘧啶来说本质上是一种未知的反应），该方法利用碘（ III ）试剂对具有多个反应性的底物中的缺电子氮杂环提供非常高的选择性位置并防止过度氧化成羰基产物。关键反应副产物的鉴定支持了在成键步骤中涉及自由基偶联的机制。

  DOI：

  10.1039/d4ob00268g

文献信息

• Chemical-Vapor-Deposited Materials for High Thermal Conductivity Applications
  作者：Jitendra S. Goela、Nathaniel E. Brese、Michael A. Pickering、John E. Graebner

  DOI：10.1557/mrs2001.116

  日期：2001.6

  Chemical vapor deposition (CVD) is an attractive method for producing bulk and thin-film materials for a variety of applications. In this method, gaseous reagents condense onto a substrate and then react to produce solid materials. The materials produced by CVD are theoretically dense, highly pure, and have other superior properties.

  化学气相沉积（CVD）是一种用于生产各种应用的块状和薄膜材料的吸引人的方法。在这种方法中，气态试剂凝结在基底上，然后发生反应产生固体材料。CVD生产的材料在理论上是致密的、高纯度的，并具有其他优越的性能。
• Solution Structure of Some λ³ Iodanes:  An ¹⁷O NMR and DFT Study
  作者：Francesca Mocci、Gianluca Uccheddu、Angelo Frongia、Giovanni Cerioni

  DOI：10.1021/jo070111h

  日期：2007.5.1

  The structure of a series of I-O bonded bis(acyloxy)iodoarenes and benzoiodoxolones in chloroform solution has been investigated by O-17 NMR spectroscopy and by density functional theory (DFT) calculations, employing the PBE0 functional together with the LANL2DZ basis set extended with polarization (d) and diffuse (p) functions. This combined approach allowed us to ascertain that, although these classes of lambda(3) iodanes maintain in chloroform solution their solid state "T-shaped" structure, a degenerate [1,3] sigmatropic shift of iodine between the two oxygens of the acyloxy groups occurs in solution. The energy barrier involved in this process differs in the two classes, thus causing significant differences in the O-17 NMR spectra, at room temperature, of the two classes of compounds.