anti-2-bromo-3-hydroxybutanoic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: anti-2-bromo-3-hydroxybutanoic acid methyl ester
• 英文别名: Methyl erythro-2-bromo-3-hydroxybutanonate；methyl (2R,3R)-2-bromo-3-hydroxybutanoate
• 化学式: C₅H₉BrO₃
• 分子量: 197.029
• InChiKey: SFQZOVKLFZOLGS-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  巴豆酸甲酯 在 sodium bromate 、 硫酸 、 sodium hydrogensulfite 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以75%的产率得到anti-2-bromo-3-hydroxybutanoic acid methyl ester
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00098a012

文献信息

• 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。
• 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：——
• 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.