3-溴-4-羟基-4-甲基戊-2-酮 | 89238-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-溴-4-羟基-4-甲基戊-2-酮
• 英文名称: 3-Bromo-4-hydroxy-4-methyl-2-pentanone
• 英文别名: bromo-3 hydroxy-4 methyl-4 pentanone-2；3-bromo-4-hydroxy-4-methyl-pentan-2-one；Methyl-(α-brom-β-oxy-isobutyl)-keton；3-Brom-4-hydroxy-4-methyl-pentan-2-on；3-Brom-2-methyl-pentanol-(2)-on-(4)；2-Pentanone, 3-bromo-4-hydroxy-4-methyl-；3-bromo-4-hydroxy-4-methylpentan-2-one
• CAS: 89238-06-2
• 化学式: C₆H₁₁BrO₂
• 分子量: 195.056
• InChiKey: FXYYRXMIQZRMEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  243.4±20.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 在 N-溴代丁二酰亚胺(NBS) 、 水 、 C₂₀H₂₉NO₇ 作用下， 反应 2.0h， 以68%的产率得到3-溴-4-羟基-4-甲基戊-2-酮
  参考文献：
  名称：

  两亲吲哚作为水中溴化的高效相转移催化剂

  摘要：

  只需加水：在两亲性吲哚的相转移催化下，开发了一种高效、环保的水中溴化反应。作为试验反应，进行烯烃的羟基溴化和芳族溴化。

  DOI：

  10.1002/cssc.202200574

文献信息

• Etude des petits cycles—XLIII
  作者：A. Lechevallier、F. Huet、J.M. Conia

  DOI：10.1016/s0040-4020(01)91581-9

  日期：1983.1

  α-cyclopropylidene carbinols (the 1,2-addition product). Addition of methyl-lithium and lithium dimethylcuprate lead to the expected 1,2- and 1,4-addition products, respectively. The comparison of these results and those corresponding to α-isopropylidene-ketones confirms the higher tendency of α-cyclopropylidene-ketones to give 1,4-addition products; the measurement of polarographic reduction potentials confirms

  α-环亚丙基酮和醛对在酸性或碱性介质，水和盐酸中的1,4-加成甲醇显示高反应活性，从而生成α-（1-甲氧基环丙基）酮和醛α-（1-羟基环丙基）酮和α -（1-氯环丙基）酮和醛。α-环亚丙基-酮与格氏试剂的反应除α-环亚丙基-甲醇（1,2-加成产物）外，主要产生α-环丙基酮（1,4-加成产物）。甲基锂和二甲基二甲基锂锂的加入分别导致了预期的1,2-和1,4-加成产物。将这些结果与对应于α-异亚丙基-酮的结果进行比较，证实了α-环亚丙基-酮产生1,4-加成产物的趋势更高；极谱还原电位的测量结果证实了这一点，在某些情况下，这种差异。HOBr（NBS，DMSO，H2 O）与α-环亚丙基酮一起生成α-羟基β-溴代酮，而相应的α-异亚丙基酮则生成β-羟基α-溴代酮。
• Synthesis of Bromo- and Iodohydrins from Deactivated Alkenes by Use ofN-Bromo- andN-Iodosaccharin
  作者：Damijana Urankar、Irena Rutar、Barbara Modec、Darko Dolenc

  DOI：10.1002/ejoc.200400829

  日期：2005.6

  N-Bromo and N-iodosaccharin react with electron-deficient alkenes such as α,β-unsaturated ketones, acids, esters and nitriles in aqueous organic solvents, yielding the corresponding halohydrins in good yields. The reactions take place at room temperature, mostly within short reaction times and with high antistereoselectivity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  N-溴和 N-碘糖精在水性有机溶剂中与缺电子烯烃如 α,β-不饱和酮、酸、酯和腈反应，以良好的收率生成相应的卤代醇。反应在室温下进行，大部分反应时间短且具有高抗立体选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• 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.
• 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：——
• Amphiphilic Indoles as Efficient Phase‐Transfer Catalysts for Bromination in Water
  作者：Qingyu Zhang、Yongyuan Xu、Xiaochen Liang、Zhihai Ke

  DOI：10.1002/cssc.202200574

  日期：2022.6.22

  Just add water: Under the phase-transfer catalysis of amphiphilic indoles, an efficient and environmentally friendly bromination in water is developed. As test reactions, hydroxybromination of olefins and aromatic bromination are conducted.

  只需加水：在两亲性吲哚的相转移催化下，开发了一种高效、环保的水中溴化反应。作为试验反应，进行烯烃的羟基溴化和芳族溴化。