meso-1,4-Dibrom-butan-2,3-diol | 1947-59-7

• 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: meso-1,4-Dibrom-butan-2,3-diol
• 英文别名: meso-1,4-Dibrom-butandiol-(2,3)；L-1,4-Dibrom-2,3-butandiol；rac. 1.4-Dibrom-butandiol-(2.3)；d,l-1,4-Dibrom-2.3-butandiol；Hochschmelzendes 1.4-Dibrom-butandiol-(2.3)；meso-1,4-dibromo-butane-2,3-diol；1,4-dibromo-1,4-dideoxy-erythritol；meso-1.4-Dibrom-2.3-butandiol；D-1,4-Dibrom-2,3-butandiol；Dibromo-meso-erythritol；(2S,3R)-1,4-dibromobutane-2,3-diol
• CAS: 1947-59-7
• 化学式: C₄H₈Br₂O₂
• 分子量: 247.914
• InChiKey: XOWDQAHYPSENAC-ZXZARUISSA-N

物化性质

• 熔点：
  136-137.5 °C
• 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

• 海关编码：
  2905590090

反应信息

• 作为反应物：
  描述：

  meso-1,4-Dibrom-butan-2,3-diol 生成 Erythritol
  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：

  Erythritol 在 乙酰溴 作用下， 以 1,4-二氧六环 为溶剂， 生成 meso-1,4-Dibrom-butan-2,3-diol
  参考文献：
  名称：

  Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω-dibromoalditol derivatives

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)00442-7

文献信息

• Synthesis of new sugar derivatives having potential antitumour activity
  作者：J. Kuszmann、L. Vargha

  DOI：10.1016/s0008-6215(00)82294-6

  日期：1966.11

  Abstract With polyhydroxy compounds, such as sugars and sugar alcohols, bis(2-chloroethyl)phosphoramidic dichloride ( 1 ) gave mixtures of cyclic derivatives in stereoisomeric forms analogous to benzylidene derivatives. In several cases, homogeneous products were isolated and their structures elucidated. The following compounds were obtained: 1,2- O -isopropylidene-α- D -glucofuranose cyclic 5,6-[

  摘要与糖和糖醇等多羟基化合物一起，双（2-氯乙基）磷酰氨基二氯化物（1）得到类似于亚苄基衍生物的立体异构形式的环状衍生物混合物。在某些情况下，分离出均质产物并阐明其结构。得到以下化合物：1,2-O-异亚丙基-α-D-葡糖呋喃糖环状的5,6- [双（2-氯乙基）氨基甲酸酯]（4），顺式和反式-1,4-二-O-甲磺酰基赤藓糖醇环2,3- [双（2-氯乙基）氨基磷酸酯]（11，13），顺式和反式-1,4-二溴-1,4-二脱氧赤藓糖醇环2,3- [双（2-氯乙基）氨基磷酸酯（ 12、14）。用氨基-多羟基化合物，形成无定形产物，大概是环状酰胺基酯，从中不能分离出均相化合物。
• Feit,P.W., Chemische Berichte, 1960, vol. 93, p. 116 - 127
  作者：Feit,P.W.

  DOI：——

  日期：——
• 158. Some potentially cytotoxic methylnitrosamines
  作者：F. Bergel、Stanley S. Brown、C. L. Leese、G. M. Timmis、Roy Wade

  DOI：10.1039/jr9630000846

  日期：——
• 547. Some reactions of 1 : 2–3 : 4-diepoxybutane
  作者：W. F. Beech

  DOI：10.1039/jr9510002483

  日期：——
• Champion, Zeitschrift fur Chemie, 1871, p. 348
  作者：Champion

  DOI：——

  日期：——