undec-10-enyl β-D-galactopyranoside | 134078-54-9

• 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: undec-10-enyl β-D-galactopyranoside
• 英文别名: undec-10-enyl-β-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-undec-10-enoxyoxane-3,4,5-triol
• CAS: 134078-54-9
• 化学式: C₁₇H₃₂O₆
• 分子量: 332.437
• InChiKey: JVPZFKPXWHKTKZ-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  undec-10-enyl β-D-galactopyranoside 在 Grubbs catalyst first generation 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 21.33h， 生成 1,20-bis-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyloxy)eicos-10-ene
  参考文献：
  名称：

  Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis

  摘要：

  A series of galactose-based surfactants with various structures likely to display new interesting properties were synthesized. Four monocatenary surfactants were elaborated by microwave-assisted galactosylation of undecanol or 10-undecenol. These compounds were slightly soluble in water. Their tensioactive properties were determined at 45 degreesC. Olefin metathesis was used to synthesize the two single-chain bolaforms from undec-10-enyl galactopyranosides; two pseudomacrocyclic bolaforms were prepared by grafting two carbamates at O-4 and O-4' sugar positions of the single-chain bolaforms. These four surfactants are insoluble in water and undergo monolayer compression. Cyclization of these bolaforms by olefin metathesis led to macrocyclic surfactant analogues of archaeobacterial membrane components. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.03.003
• 作为产物：
  描述：

  10-十一烯-1-醇 在 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.23h， 生成 undec-10-enyl β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis

  摘要：

  A series of galactose-based surfactants with various structures likely to display new interesting properties were synthesized. Four monocatenary surfactants were elaborated by microwave-assisted galactosylation of undecanol or 10-undecenol. These compounds were slightly soluble in water. Their tensioactive properties were determined at 45 degreesC. Olefin metathesis was used to synthesize the two single-chain bolaforms from undec-10-enyl galactopyranosides; two pseudomacrocyclic bolaforms were prepared by grafting two carbamates at O-4 and O-4' sugar positions of the single-chain bolaforms. These four surfactants are insoluble in water and undergo monolayer compression. Cyclization of these bolaforms by olefin metathesis led to macrocyclic surfactant analogues of archaeobacterial membrane components. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.03.003

文献信息

• Novel class of non-ionic monocatenary and bolaform alkylglycoside surfactants. Synthesis by microwave-assisted glycosylation and olefin cross-metathesis or by ‘click-chemistry’: physicochemical studies
  作者：Virginie Neto、Robert Granet、Pierre Krausz

  DOI：10.1016/j.tet.2010.03.115

  日期：2010.6

  We develop herein the synthesis of a new class of monocatenary and bolaform surfactants from d-glucose, d-galactose and lactose. Two main pathways have been investigated: microwave-assisted glycosylation followed by olefin cross-metathesis, and the one-step click-chemistry methodology. Tensioactive properties of these new compounds have been studied in order to characterize the physicochemical behaviour

  我们在这里开发了从d-葡萄糖，d-半乳糖和乳糖合成一类新型的单链和硼酸盐表面活性剂。已经研究了两个主要途径：微波辅助糖基化和随后的烯烃交叉复分解，以及一步点击化学方法。为了表征这些新的基于碳水化合物的化合物在水中的物理化学行为，已对这些新化合物的张力活性特性进行了研究。