2,2-dibromo-1-phenylbutane-1,3-dione | 97467-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dibromo-1-phenylbutane-1,3-dione
• CAS: 97467-19-1
• 化学式: C₁₀H₈Br₂O₂
• 分子量: 319.98
• InChiKey: AHOTWKZVUYVPGC-UHFFFAOYSA-N

物化性质

• 沸点：
  314.8±37.0 °C(Predicted)
• 密度：
  1.802±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dibromo-1-phenylbutane-1,3-dione 在 水 、 sodium sulfite 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 以188 mg的产率得到2-bromo-1-phenyl-1,3-butanedione
  参考文献：
  名称：

  TsNBr 2介导的炔烃的氧化功能化

  摘要：

  通过控制TsNBr 2介导的过程，开发了炔烃的氧化转化的新方法。炔烃可以很容易地通过氧溴化-脱溴序列转化为酮和α-溴代酮。在室温下，在丙酮和水的混合物中依次用TsNBr 2，KI和Na 2 SO 3处理炔烃时，可获得相应的酮。另一方面，用TsNBr 2和Na 2 SO 3处理炔烃在室温下，在乙酸乙酯，丙酮和水的混合物中，可生成相应的α-溴代酮。还可以在室温下使用TsNBr 2在很短的时间内由相应的炔烃合成1-溴炔烃。在所有情况下，都可获得相应产品的优异收率。

  DOI：

  10.1016/j.tet.2016.05.017
• 作为产物：
  描述：

  1-苯基-1,3-丁二酮 在 lead(IV) acetate 、 zinc dibromide 作用下， 以 乙腈 为溶剂， 反应 5.3h， 以85%的产率得到2,2-dibromo-1-phenylbutane-1,3-dione
  参考文献：
  名称：

  亲核卤化物向亲电卤化物的转化：使用金属卤化物/四乙酸铅对吖嗪酮、酰胺和羰基化合物进行高效和选择性卤化

  摘要：

  AlCl 3 /Pb(OAc) 4 和ZnBr 2 /Pb(OAc) 4 是有效的亲电子N-和α-C-卤化剂。使用在乙腈中的 AlCl 3 /Pb(OAc) 4 和 ZnBr 2 /Pb(OAc) 4 对各种吖酮、酰胺和羰基化合物进行化学选择性和区域选择性 N-或 α-C-卤化，收率良好至极好。

  DOI：

  10.1055/s-2006-926224

文献信息

• Divergent Synthesis of α,α-Dihaloamides through α,α-Dihalogenation of β-Oxo Amides by Using<i>N</i>-Halosuccinimides
  作者：Jia Wang、Hongtao Li、Dingyuan Zhang、Peng Huang、Zikun Wang、Rui Zhang、Yongjiu Liang、Dewen Dong

  DOI：10.1002/ejoc.201300341

  日期：2013.8

  An efficient and divergent one-pot synthesis of α,α-dihaloamides from readily available β-oxo amides based on the selection of reaction conditions is reported. α,α-Dihalo-β-oxo amides were produced by treating β-oxo amides with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) in water at room temperature, whereas α,α-dihaloacetamides were synthesized by subjecting β-oxo amides to NCS or NBS in

  报道了基于反应条件的选择，从容易获得的 β-氧代酰胺中高效且多样化的一锅法合成 α,α-二卤代酰胺。α,α-二卤代-β-氧代酰胺是通过在室温下用 N-氯代琥珀酰亚胺 (NCS) 或 N-溴代琥珀酰亚胺 (NBS) 在水中处理 β-氧代酰胺来生产的，而 α,α-二卤代乙酰胺是通过使在回流下在乙醇中将氧代酰胺转化为 NCS 或 NBS。
• Trihaloisocyanuric acids as convenient reagents for regioselective halogenation of β-dicarbonyl compounds
  作者：Gabriela F. Mendonça、Haryadylla C. Sindra、Leonardo S. de Almeida、Pierre M. Esteves、Marcio C.S. de Mattos

  DOI：10.1016/j.tetlet.2008.11.045

  日期：2009.1

  The reaction of beta-dicarbonyl compounds (beta-ketoesters and beta-diketones) with 0.34 mol equiv of trichloro and tribromoisocyanuric acids produced regioselectively the corresponding alpha-monohalo beta-dicarbonyl Compound. On the other hand, utilization of 0.68 mol equiv of the trihaloisocyanuric acid produced the alpha,alpha-dihalo beta-dicarbonyl compound. (C) 2008 Elsevier Ltd. All rights reserved.
• Regioselective synthesis of dihydrofurans from 2,2-dibromo 1,3-diones and olefins using copper
  作者：Junichi Yoshida、Shinji Yano、Tadahiro Ozawa、Nariyoshi Kawabata

  DOI：10.1021/jo00219a010

  日期：1985.9
• Reactions of Carbonyl-Conjugated Alkynes with <i>N</i>-Bromosuccinimide and <i>N</i>-Iodosuccinimide in DMF/H₂O and Methanol/Sulfuric Acid:  Syntheses of Dihalo Diketones, Dihalo Ketoesters, and Dihalo Acetals^†
  作者：Victor L. Heasley、Dale F. Shellhamer、Alfred E. Chappell、Jason M. Cox、David J. Hill、Shanna L. McGovern、Cyndi C. Eden、Charles L. Kissel

  DOI：10.1021/jo980260n

  日期：1998.6.1

  The following terminal, carbonyl-conjugated alkynes were reacted with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) in MeOH/H2SO4 to give dibromo and diiodo acetals in the indicated yields: 3-butyn-2-one, 1: NBS(75%), NIS (95%); 1-phenyl-1-propyn-1-one, 2: NBS(90%), NIS (40%); 1-hexyn-3-one, 3: NBS(90%), NIS (70%); methyl propiolate, 4: NBS (20%, not isolated), NIS (95%). 4,4-Dimethyl-1-pentyn-3-one (5) gave only a trace of dibromo acetal and no diiodo acetal; tribromide and tetrabromide were the major products. NBS and NIS reactions required, respectively, 20% and 33 wt % of H2SO4. The reaction was unsuccessful with internal alkynes 4-phenyl-3-butyn-2-one and 3-hexyn-2-one which gave only complex mixtures of products. Alkyne 2 gave a significant yield of acetal-ketal in addition to the dihalo acetals. Both the dibromo acetal-ketal and diiodo acetal-ketal were isolated, but only the former could be hydrolyzed to the dibromo acetal. Internal, carbonyl-conjugated alkynes reacted with NBS and NIS in H2O/DMF (40:60) to give the following products in the indicated yields: 4-phenyl-3-butyn-2-one (6): 1-phenyl-3,3-dibromo-1, 3-butanedione (17, 70%), 1-phenyl-3,3-diiodo-1,3-butanedione (21, 95%); 3-hexyn-2-one (7): 3,3-dibromo-2,4-hexanedione (18, 80%), 3,3-diiodo-2,4-hexanedione (22, 95%); methyl 3-phenyl-2-propynoate (8): methyl 2,2-dibromo-3-keto-3-phenylpropanoate (19, 43%), methyl 2,2-diiodo-3-keto-3-phenylpropanoate (23, 95%); methyl 2-pentynoate(9): methyl 2,2-dibromo-3-ketopentanoate (20, 80%), methyl 2,2-diiodo-3-ketopentanoate (24, 95%). All reactions, except for 6 and 8 with NBS, required H2SO4. The terminal, carbonyl-conjugated alkyne, 3-butyn-2-one, did not give products, possibly because of oxidation of the intermediate aldehyde by NBS and NIS. Mechanisms involving electrophilic attack by halogen on the triple bond and an acid-catalyzed mechanism are discussed.
• YOSHIDA, JUN-ICHI;YANO, SHINJI;OZAWA, TADAHIRO;KAWABATA, NARIYOSHI, J. ORG. CHEM., 1985, 50, N 19, 3467-3473
  作者：YOSHIDA, JUN-ICHI、YANO, SHINJI、OZAWA, TADAHIRO、KAWABATA, NARIYOSHI

  DOI：——

  日期：——