2,6-diiodo-3,5-dimethylpyridine | 934372-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-diiodo-3,5-dimethylpyridine
• CAS: 934372-87-9
• 化学式: C₇H₇I₂N
• 分子量: 358.948
• InChiKey: NTDFKVRWRLAJKT-UHFFFAOYSA-N

物化性质

• 沸点：
  340.2±37.0 °C(Predicted)
• 密度：
  2.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-diiodo-3,5-dimethylpyridine 在 四(三苯基膦)钯 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Substituent Effects in Double-Helical Hydrogen-Bonded AAA-DDD Complexes

  摘要：

  AbstractTwo series of DDD and AAA hydrogen‐bond arrays were synthesized that form triply‐hydrogen‐bonded double‐helical complexes when combined in CDCl3 solution. Derivatization of the DDD arrays with electron‐withdrawing groups increases the complex association constants by up to a factor of 30 in those arrays examined. Derivatization of the AAA arrays with electron donating substituents reveals a similar magnitude effect on the complex stabilities. The effect of substitution on both types of arrays are modeled quite satisfactorily (R2 > 0.96 in all cases) as free energy relationships with respect to the sums of their Hammett substituent constants. In all, the complex stabilities can be manipulated over more than three orders of magnitude (>20 kJ mol−1) using this type of modification.

  DOI：

  10.1002/chem.201103001
• 作为产物：
  描述：

  3,5-二甲基吡啶 在 copper(l) iodide 、 硫酸 、 溴 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 2,6-diiodo-3,5-dimethylpyridine
  参考文献：
  名称：

  2,6-Dibromo-3,5-dimethylpyridine and 2,6-diiodo-3,5-dimethylpyridine

  摘要：

  The title compounds 2,6-dibromo-3,5-dimethyl-pyridine, C7H7Br2N, (I), and 2,6-diiodo-3,5-dimethyl-pyridine, C7H7I2N, (II), constitute the first structurally characterized examples of 2,6-dihalo-3,5-dimethyl-pyridines. Compound (I) crystallizes as a racemic twin with two symmetry-independent molecules in the asymmetric unit, while (II) is non-planar with the pyridine ring slightly deformed into a saddle shape, and exhibits crystallographically imposed twofold symmetry. Both (I) and (II) exhibit aromatic face-to-face pi-stacking in the solid state, although there are no other long-range inter-actions. In (I), alternate molecules are oriented at 90 degrees, resulting in X-shaped columns, while in (II), molecules pack in a parallel fashion, leading to a zigzag array.

  DOI：

  10.1107/s0108270106032732

文献信息

• Cobalt-Catalyzed C(sp²)-H Borylation: Mechanistic Insights Inspire Catalyst Design
  作者：Jennifer V. Obligacion、Scott P. Semproni、Iraklis Pappas、Paul J. Chirik

  DOI：10.1021/jacs.6b06144

  日期：2016.8.24

  borylation of unactivated arenes. The rationally designed catalysts promote effective turnover with stoichiometric quantities of arene substrate and B2Pin2. Kinetic studies on the improved catalyst, 4-(H)2BPin, established a change in turnover limiting step from C-H oxidative addition to C-B reductive elimination. The iridium congener of the optimized cobalt catalyst, 6-(H)2BPin, was prepared and crystallographically

  使用 B2Pin2（Pin = 频哪酸酯）对双（膦基）吡啶 (PNP) 钴催化 CH 硼酸化 2,6-二甲基吡啶的机理进行了全面研究。实验观察到的速率定律、氘动力学同位素效应和催化剂静止状态支持周转的鉴定限制了来自完全表征的钴 (I) 硼基中间体的 CH 活化。监测作为时间函数的催化反应表明，钴催化剂中钳子的 4 位硼化比芳烃硼化更快。循环伏安法确定了 4-BPin 的吸电子影响，这减缓了 CH 氧化加成的速度，从而降低了整体催化转化率。这一机理见解启发了下一代 4-取代 PNP 钴催化剂，该催化剂具有给电子和空间阻断甲基和吡咯烷基取代基，这些取代基对未活化芳烃的 CH 硼酸化表现出增加的活性。合理设计的催化剂通过化学计量的芳烃底物和 B2Pin2 促进有效周转。对改进的催化剂 4-(H)2BPin 的动力学研究确定了从 CH 氧化添加到 CB 还原消除的转换限制步骤的变化。制备了优化的钴催化剂
• ‘Pincer’ pyridine dicarbene complexes of nickel and their derivatives. Unusual ring opening of a coordinated imidazol-2-ylidene
  作者：David Pugh、Aimee Boyle、Andreas A. Danopoulos

  DOI：10.1039/b715769j

  日期：——

  The reaction of NiBr2(DME), DME = 1,2-dimethoxyethane, with the ‘pincer’ pyridine dicarbene ligands (C-N-C) (2) and (C-NMe-C) (2Me), (C-N-C = 2,6-bis-[(DiPP)imidazol-2-ylidene]pyridine, C-NMe-C = 2,6-bis-[(DiPP)imidazol-2-ylidene]-3,5-dimethylpyridine, DiPP = 2,6-diisopropylphenyl) gave the square planar complexes [Ni(C-N(Me)-C)Br]Br, 3·(Br)− and 3MeMe·(Br)− respectively. Transmetallation from [(C-NMe-C)2Ag2](Ag6I8)

  NiBr 2（DME）的反应二甲醚 = 1,2-二甲氧基乙烷，加上“钳子” 吡啶 二卡宾 配体（CNC）（2）和（CN Me -C）（2 Me），（CNC = 2,6-双-[（DIPP）咪唑-2-亚甲基]吡啶，CN Me -C = 2,6-双- [（DIPP）咪唑-2-亚基] -3,5-二甲基吡啶，磷酰化= 2,6-二异丙基苯基），得到正方形的平面配合物[镍（CN （Me）的-C）BR] BR，3 ·（溴）-和3 Me Me ·（Br）-。重金属化由[（CN Me -C）2 Ag 2 ]（Ag 6 I 8），6 Me Me ·（Ag 6 I 8）2-到NiBr 2（DME），得到[Ni（CN Me -C）Br]（AgI 2），3 Me Me ·（AgI 2）−。的反应3 ·（溴）-与KPF 6导致仅在离子溴化物的交换，然而的反应3 ·（溴）-用的AgBF 4在MeCN或的AgOTf在THF
• Minimal complementary hydrogen-bonded double helices
  作者：Hong-Bo Wang、Bhanu P. Mudraboyina、Jiaxin Li、James A. Wisner

  DOI：10.1039/c0cc02475a

  日期：——

  Molecular strands incorporating three hydrogen bond donor (D) or acceptor (A) heterocycles form highly stable double helical complexes through a complementary AAA–DDD array structure.

  包含三个氢键供体（D）或受体（A）杂环的分子链通过互补的AAA–DDD阵列结构形成高度稳定的双螺旋复合物。