diethyl (5-((2-mercaptoethyl)thio)pentyl)phosphonate | 1240794-70-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl (5-((2-mercaptoethyl)thio)pentyl)phosphonate
• CAS: 1240794-70-0
• 化学式: C₁₁H₂₅O₃PS₂
• 分子量: 300.423
• InChiKey: UITLCNODQFOLSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  17.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl (5-((2-mercaptoethyl)thio)pentyl)phosphonate 、 辛可尼丁 在 偶氮二异丁腈 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 diethyl (5-((2-((2-((1S,3R,4S,6S)-6-((R)-hydroxy(quinolin-4-yl)methyl)quinuclidin-3-yl)ethyl)thio)ethyl)thio)pentyl)phosphonate
  参考文献：
  名称：

  Synthesis and characterization of mesoporous zirconium phosphonates: A novel supported cinchona alkaloid catalysts in asymmetric catalysis

  摘要：

  In this paper, cinchonidine (CD) with the different arm lengths (n = 2-6) was covalently immobolized onto the backbone of zirconium phosphonate to afford a series of mesoporous zirconium phosphonates (4a-e) for the first time. It was found that zirconium phosphonates (4a-e) were conglomerated with the globular aggregates with the diameters of about 100-150 nm and possessed the surface areas of 20.8-36.2 m(2) g(-1), pore volumes of 0.219-0.498 cc g(-1) and average pore sizes of 11.7-41.5 angstrom. The TEM' images of 4a-e in organic solvent showed that these materials were easily swollen into the filiform structure with the length about several micrometers and thickness about 30-50 nm. In the field of the asymmetric catalysis, the preliminarily enantioselective addition of diethylzinc to various aldehydes catalyzed by 4a-e (35-62%e.e. in the 68-92% yield) was carried out and can be reused ten times without loss in the yield and enantiomeric excess. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2009.10.031
• 作为产物：
  描述：

  二乙基(5-溴戊基)膦酸酯 、 1,2-乙二硫醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 diethyl (5-((2-mercaptoethyl)thio)pentyl)phosphonate
  参考文献：
  名称：

  Synthesis and characterization of mesoporous zirconium phosphonates: A novel supported cinchona alkaloid catalysts in asymmetric catalysis

  摘要：

  In this paper, cinchonidine (CD) with the different arm lengths (n = 2-6) was covalently immobolized onto the backbone of zirconium phosphonate to afford a series of mesoporous zirconium phosphonates (4a-e) for the first time. It was found that zirconium phosphonates (4a-e) were conglomerated with the globular aggregates with the diameters of about 100-150 nm and possessed the surface areas of 20.8-36.2 m(2) g(-1), pore volumes of 0.219-0.498 cc g(-1) and average pore sizes of 11.7-41.5 angstrom. The TEM' images of 4a-e in organic solvent showed that these materials were easily swollen into the filiform structure with the length about several micrometers and thickness about 30-50 nm. In the field of the asymmetric catalysis, the preliminarily enantioselective addition of diethylzinc to various aldehydes catalyzed by 4a-e (35-62%e.e. in the 68-92% yield) was carried out and can be reused ten times without loss in the yield and enantiomeric excess. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2009.10.031

文献信息

• Preparation and confinement effect of a heterogeneous 9-amino-9-deoxy-epi-cinchonidine organocatalyst for asymmetric aldol addition in aqueous medium
  作者：Wei Wang、Xuebing Ma、Jingwei Wan、Jun Cao、Qian Tang

  DOI：10.1039/c2dt12390h

  日期：——

  A series of novel porous zirconium phosphonate-supported 9-amino-9-deoxy-epi-cinchonidines of general formulae Zr(OH)4−2x(O3PR)x·nH2O and Zr(HPO4)2−x(O3PR)x·nH2O with the different arm chain lengths (n = 2–6) and mean diameters of approximately 20–40 nm have been prepared as heterogeneous organocatalysts. The different microtextures of zirconium phosphonates were also obtained by using template guest

  一系列新型的多孔膦酸锆负载的9-氨基-9-脱氧表位-辛可尼定，其通式为Zr（OH）4−2 x（O 3 PR）x · n H 2 O和Zr（HPO 4）2− x（O 3 PR）x · n H 2 O具有不同的臂链长度（n = 2–6）和平均直径约为20–40 nm，已被制备为多相有机催化剂。还可以通过使用模板客体分子（例如Et 3 N，NaH 2PO 4和十二烷基苯磺酸钠。在对硝基苯甲醛向环己酮的不均相不对称醛醇缩合中，获得了优异的催化性能，特别是在水性介质中。反应完成后，可以容易地通过离心或过滤以定量收率回收那些膦酸锆负载的9-氨基-9-脱氧-表位-辛可尼定有机催化剂，并在不显着降低催化性能的情况下连续使用五次。特别地，由于无机主链的空间限制作用，分别取决于邻位基团之间的相互作用，有利地获得了羟醛加合物中可能的四种立体异构体之间的单一不同构型。硝基苯甲醛和主链的-，m-或对位，这在均匀的羟醛加成中从未观察到。