2,7-dibromocycloheptanone | 17346-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,7-dibromocycloheptanone
• 英文别名: 2,7-dibromocycloheptan-1-one
• CAS: 17346-17-7
• 化学式: C₇H₁₀Br₂O
• 分子量: 269.964
• InChiKey: PAMIRPDGXRSPTC-UHFFFAOYSA-N

物化性质

• 沸点：
  282.8±40.0 °C(Predicted)
• 密度：
  1.806±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,7-dibromocycloheptanone 在 lithium aluminium tetrahydride 、 碘 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 5.0h， 生成 syn-2,3-Dithiabicyclo<4.2.1>nonan-9-ol S-Oxide
  参考文献：
  名称：

  A general methodology for the synthesis of [2.2.1], [3.2.1+], and [4.2.1] bridged bicyclic disulfide systems

  摘要：

  A general synthesis for bridged bicyclic disulfide compounds has been refined and expanded from [3.2.1] to [2.2.1] and [4.2.1] systems. The chemical reactivity of these novel compounds has been probed through esterification and S-oxidation reactions.

  DOI：

  10.1021/jo00033a022
• 作为产物：
  描述：

  环庚酮 在 氢溴酸 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以46%的产率得到2,7-dibromocycloheptanone
  参考文献：
  名称：

  A general methodology for the synthesis of [2.2.1], [3.2.1+], and [4.2.1] bridged bicyclic disulfide systems

  摘要：

  A general synthesis for bridged bicyclic disulfide compounds has been refined and expanded from [3.2.1] to [2.2.1] and [4.2.1] systems. The chemical reactivity of these novel compounds has been probed through esterification and S-oxidation reactions.

  DOI：

  10.1021/jo00033a022

文献信息

• Microwave-assisted synthesis of α-hydroxy ketone and α-diketone and pyrazine derivatives from α-halo and α,α′-dibromo ketone
  作者：Takamitsu Utsukihara、Hiroaki Nakamura、Masashige Watanabe、C. Akira Horiuchi

  DOI：10.1016/j.tetlet.2006.10.087

  日期：2006.12

  A novel reaction of α-halo ketone (α-bromo and α-chloro ketone) with irradiation under microwave gave the corresponding α-hydroxyketone and pyrazine derivative in good yields. In the case of α,α′-dibromo ketone, α-diketone was obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxyketone, α-diketone, α-chloro ketone and pyrazine derivative.

  微波辐射下α-卤代酮（α-溴代和α-氯代酮）的新型反应可得到相应的α-羟基酮和吡嗪衍生物，收率很高。在α，α′-二溴酮的情况下，获得了α-二酮。该反应为α-羟基酮，α-二酮，α-氯酮和吡嗪衍生物的合成提供了一种新的，清洁且方便的方法。
• Addition of Indoles to Oxyallyl Cations for Facile Access to α-Indole Carbonyl Compounds
  作者：Qiang Tang、Xingkuan Chen、Bhoopendra Tiwari、Yonggui Robin Chi

  DOI：10.1021/ol300591z

  日期：2012.4.6

  A direct coupling of unprotected indoles and α-halo ketones via in situ generated oxyallyl cation intermediates is described. The reactions efficiently afford α-indole carbonyl compounds with good to quantitative yields.

  描述了未保护的吲哚和α-卤代酮通过原位生成的羟基烯丙基阳离子中间体的直接偶联。该反应有效地提供了具有良好至定量收率的α-吲哚羰基化合物。
• Model Studies for the Preparation of Oxepanes and Fused Compounds by Tandem [4+3] Cycloaddition/Ring-Opening Metathesis/Cross Metathesis
  作者：Paolo Disetti、Linda Piras、Maria Moccia、Michele Saviano、Mauro F. A. Adamo

  DOI：10.1002/ejoc.201700994

  日期：2017.11.9

  Functionalised medium-sized ether rings were prepared in an efficient manner by [4+3] cycloaddition followed by ring-opening metathesis. This procedure provided medium-sized rings, which were shown to be useful for the assembly of fused bicyclic structures present in complex natural compounds. The potential of the chemistry described in this paper to be used in synthesis has been demonstrated by the

  通过 [4+3] 环加成和开环复分解以有效的方式制备功能化的中等大小的醚环。该过程提供了中等大小的环，这些环被证明可用于组装复杂天然化合物中存在的稠合双环结构。本文中描述的化学用于合成的潜力已通过功能化的大环醚和双环结构的制备得到证明。
• Synthesis and Biological Evaluation of New Ozonides with Improved Plant Growth Regulatory Activity
  作者：Luiz C. A. Barbosa、Célia R. A. Maltha、Raphael C. Cusati、Róbson R. Teixeira、Filipe F. Rodrigues、Antônio A. Silva、Michael G. B. Drew、Fyaz M. D. Ismail

  DOI：10.1021/jf902540z

  日期：2009.11.11

  The iron oxyallyl carbocation generated from 2,7-dibromocycloheptanone was induced to undergo [4 + 3] cycloaddition reactions with various furans, affording a series of 12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one adducts. Similar methodology was used to prepare two additional cycloadducts using menthofuran and two homologous aliphatic dibromoketones. Dipolar cycloaddition of ozone to the adducts

  诱导从2,7-二溴环庚酮生成的氧氧基烯丙基碳正离子与各种呋喃进行[4 + 3]环加成反应，得到一系列的12-氧三环-[4.4.1.1 2,5 ] -dodec-3-en-11 -一个加合物。使用类似的方法，使用薄荷醇和两个同源的脂族二溴酮制备另外两个环加合物。臭氧与加合物的偶极环加成以可变的收率提供了相应的仲臭氧化物（即1,2,4-三氧戊环）。通过在B3LYP / 6-31 + G *水平上的量子力学研究了臭氧，研究了包括紧密接触的结构特征，这些紧密接触可能有助于增强臭氧的稳定性。这些臭氧化物及其相应的前体环加合物对双色高粱根系生长的影响和黄瓜在5.0×10评价-4摩尔大号-1。还评估了最活跃的环加合物和臭氧化物对杂草物种大叶番薯（Ipomoea grandifolia）和臂状臂锈菌（Brachiaria decumbens）的影响，并对结果进行了讨论。与先前在我们实验室中合成的臭氧化物相
• Electronic Donation or Steric Contraction: A Spectroscopic and Structural Analysis of Medium-Sized Constrained Rings for Potential Long-Range Hyperconjugation
  作者：Robert Lee、Bryan Bashrum、Ethan C. Cagle、Jillian Walters、Jake Massey、Monica Zanghi、Carolyn Birchfield、David French、Jessica Joy、Gabriel dos Passos Gomes、Paul A. Wiget

  DOI：10.1021/acs.joc.9b00979

  日期：2019.8.16

  the apparent Perlin effect previously reported in constrained tricyclic cycles, as well as evidence suggesting both steric contraction and long-range hyperconjugation account for the observed 1JCH perturbations. We report a true Perlin effect of 10.9 Hz in an azocane and large steric effect resulting in Δ1JC–H = 10.9 Hz in a cyclooctane.

  在这里，我们报告了1 J CH分析，自然键轨道分析和许多C，O和N约束的三环循环的X射线晶体结构。这些实验提供了先前在受约束的三环循环中报道的表观Perlin效应的性质，以及证据表明空间收缩和远距离超共轭均可解释所观察到的1 J CH扰动。我们在一个azocane并导致Δ大位阻效应报告10.9 Hz的真实效果培林1 Ĵ C-H =在环辛烷10.9赫兹。