methyl 11-(acetylthio)undecanoate | 90215-02-4

• 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: methyl 11-(acetylthio)undecanoate
• 英文别名: methyl 11-acetylthioundecanoate；methyl 11-thioacetylundecanoate；11-acetylsulfanyl-undecanoic acid methyl ester；11-Acetylmercapto-undecansaeure-methylester；Methyl 11-(acetylsulfanyl)undecanoate；methyl 11-acetylsulfanylundecanoate
• CAS: 90215-02-4
• 化学式: C₁₄H₂₆O₃S
• 分子量: 274.425
• InChiKey: OTYQUFSRSBBREN-UHFFFAOYSA-N

物化性质

• 熔点：
  39-40 °C
• 沸点：
  348.6±15.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 11-(acetylthio)undecanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以68%的产率得到methyl 11-mercaptoundecanoate
  参考文献：
  名称：

  由支链淀粉合成四糖[α-d-Glc-（1→6）-α-d-Glc-（1→4）-α-d-Glc-（1→ 4）-d-Glc]存在于人尿液中；新糖蛋白的制备

  摘要：

  摘要支链淀粉的酶水解，然后进行乙酰化和色谱分离，得到乙酰化的α-d -Glc p-（1→6）-α-d -Glc p-（1→4）-α-d -Glc p-（1→ 4）-d-Glc p，其与2-溴乙醇和三氟化硼在二氯甲烷中的醚化产物，得到2-溴乙基糖苷。描述了糖苷与3-巯基丙酸甲酯，11-巯基癸酸甲酯和十八烷硫醇的反应，还对其进行氢解得到乙基糖苷。巯基丙酸酯衍生的间隔臂糖苷已与牛血清白蛋白和匙孔血蓝蛋白偶联。

  DOI：

  10.1016/0008-6215(84)85103-4
• 作为产物：
  描述：

  11-溴十一酸 在 resin Duolit (H+) 甲基三辛基氯化铵 、 caesium carbonate 、 calcium chloride 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 methyl 11-(acetylthio)undecanoate
  参考文献：
  名称：

  由支链淀粉合成四糖[α-d-Glc-（1→6）-α-d-Glc-（1→4）-α-d-Glc-（1→ 4）-d-Glc]存在于人尿液中；新糖蛋白的制备

  摘要：

  摘要支链淀粉的酶水解，然后进行乙酰化和色谱分离，得到乙酰化的α-d -Glc p-（1→6）-α-d -Glc p-（1→4）-α-d -Glc p-（1→ 4）-d-Glc p，其与2-溴乙醇和三氟化硼在二氯甲烷中的醚化产物，得到2-溴乙基糖苷。描述了糖苷与3-巯基丙酸甲酯，11-巯基癸酸甲酯和十八烷硫醇的反应，还对其进行氢解得到乙基糖苷。巯基丙酸酯衍生的间隔臂糖苷已与牛血清白蛋白和匙孔血蓝蛋白偶联。

  DOI：

  10.1016/0008-6215(84)85103-4

文献信息

• Bis-type modifiers in polymerization. II. Comparison of effectiveness of various compounds in emulsion butadiene and bulk styrene polymerizations
  作者：A. J. Costanza、R. J. Coleman、R. M. Pierson、C. S. Marvel、Charles King

  DOI：10.1002/pol.1955.120178501

  日期：1955.7

  AbstractThe present paper describes the preparation and evaluation of the effectiveness as modifiers of a number of compounds of bis‐type structure—principally aryl disulfides—in bulk styrene and emulsion butadiene polymerizations. This work endeavors to explore some of the objectives described in the first paper of this series, and deals primarily with attempts to gain quantitative information on the effect of the nature and location of substituting groups with respect to the dissociating bond. The compounds examined include both those containing reactive groups attached and those lacking such groups. A number of the preparations are now compounds. Evaluations in 50°C. bulk styrene were carried out with the objective of eliminating the complications of the diffusion factor always present in emulsion systems. Generally speaking, the correlation between effectiveness in bulk styrene and 50°C. emulsion butadiene was quite good, though there were exceptions. It was found that the modifier activity of many compounds in emulsion butadiene could be enhanced by predispersing them in the aqueous phase—presumably a result of minimizing the importance of diffusion rate. Some of the modifiers were also tested in a low temperature butadiene emulsion system. Aryl disulfides continue to offer the most promise from the standpoint of combining the features of attaining high transfer constants and ease of incorporating desired reactive groups. Some compounds had adequate activity in emulsion butadiene polymerizations for use as practical modifiers. However, it has not yet been established that these compounds cleave to give one‐half the molecule on each end of the butadiene polymer chain, as has been done for styrene polymers.
• Reddie, R.N., Synthetic Communications, 1987, vol. 17, # 9, p. 1129 - 1140
  作者：Reddie, R.N.

  DOI：——

  日期：——
• REDDIE, R. N., SYNTH. COMMUN., 17,(1987) N 9, 1129-1139
  作者：REDDIE, R. N.

  DOI：——

  日期：——
• Sodium Borohydride–Mediated Transesterification
  作者：Grigoriy Sereda、Swetha Pothula、James Dreessen

  DOI：10.1080/00397910903072438

  日期：2010.4.12

  presence of sodium borohydride, esters react with alcohols with formation of the corresponding esters. The reaction is sensitive to the solvent, structure of the ester, and is often concurrent with reduction. Thioesters containing an ester group can be selectively cleaved by the reagent. Both esters and thioesters attached to solid support are resistant toward sodium borohydride. The in situ prepared

  在硼氢化钠存在下，酯与醇反应形成相应的酯。该反应对溶剂、酯的结构敏感，并且通常与还原同时发生。含有酯基的硫酯可以被试剂选择性地裂解。附着在固体支持物上的酯和硫酯都耐硼氢化钠。引入原位制备的四烷氧基硼酸钠作为酯交换的有效试剂和催化剂。
• Synthesis from pullulan of spacer-arm, lipid, and ethyl glycosides of a tetrasaccharide [α-d-Glc-(1→6)-α-d-Glc-(1→4)-α-d-Glc-(1→4)-d-Glc] found in human urine; preparation of neoglycoproteins
  作者：Jan Dahmén、Torbjörn Frejd、Göran Magnusson、Ghazi Noori、Anne-Sofie Carlström

  DOI：10.1016/0008-6215(84)85103-4

  日期：1984.4

  2-bromoethanol and boron trifluoride etherate in dichloromethane, gave the 2-bromoethyl glycoside. The reactions of the glycoside with methyl 3-mercaptopropionate, methyl 11-mercaptoundecanoate, and octadecanethiol are described, and also its hydrogenolysis to give an ethyl glycoside. The mercaptopropionate-derived, spacer-arm glycoside has been coupled to bovine serum albumin and keyhole limpet haemocyanin

  摘要支链淀粉的酶水解，然后进行乙酰化和色谱分离，得到乙酰化的α-d -Glc p-（1→6）-α-d -Glc p-（1→4）-α-d -Glc p-（1→ 4）-d-Glc p，其与2-溴乙醇和三氟化硼在二氯甲烷中的醚化产物，得到2-溴乙基糖苷。描述了糖苷与3-巯基丙酸甲酯，11-巯基癸酸甲酯和十八烷硫醇的反应，还对其进行氢解得到乙基糖苷。巯基丙酸酯衍生的间隔臂糖苷已与牛血清白蛋白和匙孔血蓝蛋白偶联。