erythro-2-Bromo-3-hydroxybutanoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: erythro-2-Bromo-3-hydroxybutanoic acid
• 英文别名: (R^*,R^*)-2-bromo-3-hydroxybutanoic acid；anti-2-bromo-3-hydroxybutanoic acid；(+/-)-erythro-2-Brom-3-hydroxy-buttersaeure；(+/-)-erythro-2-bromo-3-hydroxy-butyric acid；2-Brom-3-hydroxy-buttersaeure, (+/-)-erythro Form；(2S,3S)-2-bromo-3-hydroxybutanoic acid
• 化学式: C₄H₇BrO₃
• 分子量: 183.002
• InChiKey: LCHQHZMPERBYFH-HRFVKAFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  erythro-2-Bromo-3-hydroxybutanoic acid 在 氨 、 水 作用下， 生成 L-别苏氨酸
  参考文献：
  名称：

  Carter; Zirkle, Journal of Biological Chemistry, 1949, vol. 178, p. 711

  摘要：

  DOI：
• 作为产物：
  描述：

  巴豆酸 在 sodium bromate 、 硫酸 、 sodium hydrogensulfite 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到erythro-2-Bromo-3-hydroxybutanoic acid
  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

• Reaction of N-Haloamide. XX. Bromo-formyloxylation of α, β-Unsaturated Esters with N, N-Dibromobenzenesulfonamide and Formic Acid
  作者：YOSHIO UENO、AKEMI YAMASAKI、HIROMI TERAUCHI、SHOJI TAKEMURA

  DOI：10.1248/cpb.22.1646

  日期：——

  α, β-Unsaturated esters were made to react with N, N-dibromobenzenesulfonamide and formic acid in chloroform to give bromo-formyloxyesters. Methyl acrylate (1a), ethyl crotonate (2a), ethyl trans-cinnamate (3a), methyl tiglate (4a), methyl methacrylate (5a), and methyl phenylacrylate (6a) gave methyl 2-bromo-3-formyloxypropionate (1b), ethyl erythro-2-bromo-3-formyloxybutyrate (2b), ethyl erythro-2-bromo-3-formyloxy-3-phenylpropionate (3b), methyl erythro-2-bromo-3-formyloxy-2-methylbutyrate (4b), a mixture of methyl 3-bromo-2-formyloxy-2-methylpropionate (5b) and methyl 2-bromo-3-formyloxy-2-methylpropionate (5c), and methyl 3-bromo-2-formyloxy-2-phenylpropionate (6b) respectively in good yields.

  α, β-不饱和酯与N, N-二溴苯磺酰胺和甲酸在氯仿中反应，生成溴代甲酰氧基酯。甲基丙烯酸酯（1a）、乙基巴豆酸酯（2a）、乙基反式肉桂酸酯（3a）、甲基惕格酸酯（4a）、甲基甲基丙烯酸酯（5a）和甲基苯基丙烯酸酯（6a）分别以良好的产率生成甲基2-溴-3-甲酰氧基丙酸酯（1b）、乙基erythro-2-溴-3-甲酰氧基丁酸酯（2b）、乙基erythro-2-溴-3-甲酰氧基-3-苯基丙酸酯（3b）、甲基erythro-2-溴-3-甲酰氧基-2-甲基丁酸酯（4b）、甲基3-溴-2-甲酰氧基-2-甲基丙酸酯（5b）和甲基2-溴-3-甲酰氧基-2-甲基丙酸酯（5c）的混合物以及甲基3-溴-2-甲酰氧基-2-苯基丙酸酯（6b）。
• Stereoselective Cobalt-Catalyzed Cross-Coupling Reactions of Arylzinc Chlorides with α-Bromolactones and Related Derivatives
  作者：Maximilian S. Hofmayer、Alisa Sunagatullina、Daniel Brösamlen、Philipp Mauker、Paul Knochel

  DOI：10.1021/acs.orglett.9b04564

  日期：2020.2.21

  α-Bromolactones bearing a substituent in the β-position undergo a highly trans-diastereoselective arylation with arylzinc chlorides in the presence of 10-20% CoCl2 and 10-20% PPh3 in THF under mild conditions (25 °C, 16 h) leading to optically enriched α-arylated lactones and protected aldol products (99% ee) in 52-96% yield. The synthetic utility of this arylation was demonstrated by the stereoselective

  在温和条件下（25°C，16 h）在THF中存在10-20％CoCl2和10-20％PPh3的情况下，在芳基氯化锌存在下，在β位带有取代基的α-溴内酯经历高度反式-非对映选择性芳基化反应。以光学方式富集α-芳基化内酯和受保护的羟醛产物（99％ee），产率为52-96％。该芳基化的合成效用通过人工类胡萝卜素MOM保护的munduserol衍生物的立体选择性制备证明。
• A stereocontrolled formal total synthesis of (±)-thienamycin
  作者：Masao Shiozaki、Tetsuo Hiraoka

  DOI：10.1016/0040-4020(82)85029-1

  日期：1982.1

  The stereocontrolled synthesis of a key intermediate 20 for the preparation of (±)-thienamycin 1 is described. The key steps in the synthesis are the formation of the β-lactam ring by cyclization of the amide 5 via a complete SN2 mechanism, and the stereospecific conversion of the azetidinone 5 to the amide (trans-11) which have the correct relative configurations at three contiguous chiral centres

  描述了用于制备（±）-硫霉素1的关键中间体20的立体控制合成。在合成中的关键步骤是β内酰胺环的由所述酰胺的环化反应形成5经由全S Ñ 2机构，和氮杂环丁酮的立体有择转化5为酰胺（反式- 11），其具有相对正确在三个连续的手性中心配置。推测氮杂环丁酮16E向无N的氮杂环丁酮17和硒化物化合物18的转化机理。
• Bromolysis and Iodolysis of α,β-Epoxycarboxylic Acids in Water Catalyzed by Indium Halides
  作者：David Amantini、Francesco Fringuelli、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/jo0156215

  日期：2001.6.1

  The ring opening of alpha,beta -epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-beta -monoalkylated epoxycarboxylic acids at pH 4.0 was completely ol-regioselective and anti diastereoselective. The InCl3-catalyzed iodolysis of a variety of alpha,beta -epoxycarboxylic acids at pH 1.5 gave the corresponding anti beta -iodohydrins in 88-95% yields. The one-pot synthesis of the alpha- and beta -hydroxyhexanoic acids, starting from the corresponding alpha,beta -epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH4-InCl3 in water, has been performed.
• Buckles et al., Proceedings of the Iowa Academy of Science, 1952, vol. 59, p. 170,173
  作者：Buckles et al.

  DOI：——

  日期：——