5,5-Dibromo-4-octanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-Dibromo-4-octanone
• 英文别名: 5,5-dibromooctan-4-one
• 化学式: C₈H₁₄Br₂O
• 分子量: 286.007
• InChiKey: AODBHCPEZLLWHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-辛炔 在 水 、 1,3-二溴-1,3,5-三嗪-2,4,6-三酮 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以77%的产率得到5,5-Dibromo-4-octanone
  参考文献：
  名称：

  炔烃与二溴异氰尿酸反应合成α，α-二溴酮，1,2-二溴代烯酮和1,2-二酮的替代作用

  摘要：

  内部炔烃与二溴异氰尿酸/ H 2 O反应，得到α，α-二溴酮和1,2-二酮衍生物。具有活化基团的二芳基炔烃提供1,2-二酮衍生物作为主要产物，而具有非活化基团的二芳基炔烃或烷基芳基炔烃提供的α，α-二溴酮衍生物为主要产物。此外，带有失活基团的二芳基炔烃可提供1,2-二溴烯烃。该反应在室温下进行，并且在大多数情况下显示出良好的产率。已经基于实验观察和密度泛函理论（DFT）计算提出了反应途径。

  DOI：

  10.1002/adsc.201801535

文献信息

• Catalyst- and Metal-Free Rapid Functionalizations of Alkynes Using TsNBr2
  作者：Lal Yadav、Ruchi Chawla、Atul Singh

  DOI：10.1055/s-0033-1339194

  日期：——

  A very rapid (3–12 min) and efficient method has been developed for a one-pot synthesis of α,α-dibromoalkanones and β-bromoenol alkanoates directly from alkynes using N , N -dibromo- p -toluenesulfonamide (TsNBr 2 ). The protocol is embellished with features like ambient temperature, high regioselectivity, operational simplicity, and metal- and catalyst-free conditions.

  已经开发了一种非常快速（3-12 分钟）且有效的方法，用于使用 N , N - 二溴对甲苯磺酰胺 (TsNBr 2 ) 直接从炔烃一锅合成 α,α-二溴链烷酮和 β-溴烯醇链烷酸酯。该协议具有环境温度、高区域选择性、操作简单以及无金属和无催化剂条件等特点。
• CoFe₂O₄–SiO₂–SO₃H nanocomposite as a magnetically recoverable catalyst for oxidative bromination of alkynes
  作者：Mintu Maan Dutta、Kamal Krishna Rajbongshi、Prodeep Phukan

  DOI：10.1080/00397911.2017.1376333

  日期：2017.12.17

  ABSTRACT A hybrid catalyst has been prepared by incorporating sulfonic acid onto cobalt ferrite magnetic nanoparticles. The catalyst was successfully applied for rapid (20 min) synthesis of α,α-dibromoketones directly from alkynes and NBS. The reaction works well in the presence of 10 wt% of the catalyst at room temperature to produce the desired products in high yield. The catalyst could be recovered

  摘要 通过将磺酸掺入铁氧体钴磁性纳米粒子上制备了一种混合催化剂。该催化剂已成功应用于直接从炔烃和 NBS 快速（20 分钟）合成 α,α-二溴酮。该反应在室温下在 10 wt% 的催化剂存在下运行良好，以高产率生产所需的产物。催化剂可以使用外部磁铁回收并重复使用，活性不会发生明显变化。图形概要
• A New Synthetic Method of Preparing Iodohydrin and Bromohydrin Derivatives through in situ Generation of Hypohalous Acids from H5IO6 and NaBrO3 in the Presence of NaHSO3
  作者：Haruyoshi Masuda、Kiyoshi Takase、Masahiro Nishio、Akira Hasegawa、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1021/jo00098a012

  日期：1994.9

  Hypohydrous acids such as hypoiodous acid (IOH) and hypobromous acid (BrOH) were found to be easily generated from H5IO6 and NaBrO3 in the presence of an appropriate reducing agent such as NaHSO3. Iodohydrin and bromohydrin derivatives were synthesized in good yields from the reaction of a wide variety of organic compounds bearing carbon-carbon double bonds, with H5IO6 or NaBrO3 and NaHSO3. The iodohydroxylation of internal alkenes was achieved with high stereoselectivity to give anti products, although no stereoselectivity was observed in the bromohydroxylation of these alkenes. It was found that allylic alcohols undergo iodohydroxylation in anti-Markovnikov fashion to form iodo diols in good yields. Treatment of alkynes with H5IO6 combined with NaHSO3 afforded the corresponding ketones in fair yields, but the same treatment with NaBrO3 rather than H5IO6 produced the corresponding alpha,alpha-dibromo ketones along with small amounts of the dibromoalkenes.
• Selective 1,2-dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides
  作者：Jinhua Liu、Wenjuan Li、Chao Wang、Yao Li、Zhiping Li

  DOI：10.1016/j.tetlet.2011.06.047

  日期：2011.8

  1,2-Dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides can be selectively realized through using different reaction conditions. alpha,beta-Dihalo alkenes were obtained exclusively using THF as solvent without using any catalyst, while alpha,alpha-dihalo ketones were synthesized using a mixed solvent of THF and H2O in the presence of FeCl3 center dot 6H(2)O. Terminal aromatic alkynes are smoothly transformed into alpha,alpha-dihalo ketones on water without a catalyst. (C) 2011 Elsevier Ltd. All rights reserved.
• Masuda Haruyoshi, Takase Kiyoshi, Nishio Masahiro, Hasegawa, Akira, Nishi+, J. Org. Chem, 59 (1994) N 19, S 5550- 5555
  作者：Masuda Haruyoshi, Takase Kiyoshi, Nishio Masahiro, Hasegawa, Akira, Nishi+

  DOI：——

  日期：——