(S,S)-1,4-dibromo-butane-2,3-diol | 299-70-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (S,S)-1,4-dibromo-butane-2,3-diol
• 英文别名: 1,4-dibromo-D-1,4-dideoxy-threitol；(2R,3R)-1,4-Dibrom-butan-2,3-diol；(2s,3s)-1,4-Dibromobutane-2,3-diol
• CAS: 299-70-7；1947-59-7；14396-65-7；15410-44-3；24677-99-4
• 化学式: C₄H₈Br₂O₂
• 分子量: 247.914
• InChiKey: XOWDQAHYPSENAC-QWWZWVQMSA-N

物化性质

• 熔点：
  82-84 °C (lit.)
• 沸点：
  365.3±42.0 °C(Predicted)
• 密度：
  2.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S39
• 危险类别码：
  R41,R37/38

制备方法与用途

用途 

用作药物中间体

反应信息

• 作为反应物：
  描述：

  (S,S)-1,4-dibromo-butane-2,3-diol 在 氢氧化钾 、 乙醚 作用下， 生成 (2S)-2-[(2S)-环氧乙烷-2-基]环氧乙烷
  参考文献：
  名称：

  Griner, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1893, vol. 117, p. 554

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R)-2-[(2R)-环氧乙烷-2-基]环氧乙烷 在 氢溴酸 作用下， 生成 (S,S)-1,4-dibromo-butane-2,3-diol
  参考文献：
  名称：

  Feit,P.W., Chemische Berichte, 1960, vol. 93, p. 116 - 127

  摘要：

  DOI：

文献信息

• Preparation of dl-2,3,4-trihydroxybutylarsonic acid and dl-2,3-dihydroxybutane-1,4-bis(arsonic acid): starting compounds for novel arsonolipids
  作者：Gerasimos M. Tsivgoulis、Maria A. Lala、Panayiotis V. Ioannou

  DOI：10.1016/j.chemphyslip.2007.04.011

  日期：2007.8

  aqueous alkaline sodium arsenite, "Na(3)AsO(3)", gave mixtures of the title arsonic acids which can be separated by anion exchange resin. Characterization of by-products leads to a better understanding of these reactions. These compounds are valuable intermediates for the preparation of novel arsonic acids and bis(arsonic acids).

  DL-1,3-丁二烯二环氧化合物和DL-1,4-二溴-2,3-丁二醇与碱性亚砷酸钠水溶液“ Na（3）AsO（3）”的反应，得到标题砷酸的混合物可以用阴离子交换树脂分离。副产物的表征导致对这些反应的更好理解。这些化合物是制备新型砷酸和双（砷酸）的有价值的中间体。
• Stereoisomere 1,4-Di-O-methansulfonyl-butan-1,2,3,4-tetrole
  作者：P.W. Feit

  DOI：10.1016/s0040-4039(01)91680-6

  日期：1961.1
• Bose et al., Journal of the Chemical Society, 1959, p. 3314,3319
  作者：Bose et al.

  DOI：——

  日期：——
• Cyclocondensation of oxalyl chloride with 1,2-glycols
  作者：Takehiko Iida、Taisuke Itaya

  DOI：10.1016/s0040-4020(01)81546-5

  日期：1993.1

  Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-1, and erythro-1,2-disubstituted ethylene glycols 1f, m,o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n,p,q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate for the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.
• Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω-dibromoalditol derivatives
  作者：Sami Halila、Mohammed Benazza、Gilles Demailly

  DOI：10.1016/s0040-4039(01)00442-7

  日期：2001.5

  Polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane rings have been readily obtained in excellent yields (78-95%) from thioheterocyclisation of the bielectrophilic petacetylated alpha,omega -dibrominated derivatives of tetritols (erythritol (1) and D,L-threitol (4)), pentitols: (xylitol (7), ribitol (10) and D-arabinitol (14)) and hexitols (D-mannitol (17) and D-glucitol (20)), respectively. With 2,3,4,5-tetra-O-acetyl-1,6-dibromo-1,6-dideoxy-D-glucitol (21) as substrate, the unexpected 2,6-anhydro derivative 25 was obtained. This could be attributed to previous S-= regioselective nucleophilic attack at C-1 position followed by 1,2-transesterification and 2,6-O-heterocyclisation. The preferential attack at C-1 of the D-glucitol derivative 21 subsequently allowed a facile direct synthesis in good yields of 2,3,4,5,6-penta-O-acetyl-1-bromo-1-deoxy-D-glucitol (26), 2,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiobutyl-1-deoxy-D-glucitol (28) and 2,3,3,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiooctyl-1-deoxy-D-glucitol (28). (C) 2001 Elsevier Science Ltd. All rights reserved.