((1S,2R)-2-Hydroxymethyl-2-methyl-3-oxo-cyclopentyl)-thioacetic acid S-ethyl ester | 138962-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1S,2R)-2-Hydroxymethyl-2-methyl-3-oxo-cyclopentyl)-thioacetic acid S-ethyl ester
• CAS: 138962-46-6
• 化学式: C₁₁H₁₈O₃S
• 分子量: 230.328
• InChiKey: XNAHATBLIDYRRH-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (2-Methyl-3-trimethylsilanyloxy-cyclopent-2-enyl)-thioacetic acid S-ethyl ester 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (4aS,7aR)-7a-methyl-4,4a,5,6-tetrahydro-1H-cyclopenta[c]pyran-3,7-dione 、 ((1S,2R)-2-Hydroxymethyl-2-methyl-3-oxo-cyclopentyl)-thioacetic acid S-ethyl ester
  参考文献：
  名称：

  在水性介质中作为稳定路易斯酸的镧系元素三氟甲磺酸盐。Yb(OTf)3催化甲硅烷醇醚与商用甲醛溶液的羟甲基化反应

  摘要：

  通过催化量的三氟甲磺酸镱 (III) (Yb(OTf)3)（一种在水性介质中是稳定的路易斯酸），甲硅烷基烯醇醚与商业甲醛溶液顺利反应，以高产率得到相应的羟甲基化加合物。其他镧系元素三氟甲磺酸盐也被发现是有效的。

  DOI：

  10.1246/cl.1991.2187

文献信息

• Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media
  作者：Shu Kobayashi、Iwao Hachiya

  DOI：10.1021/jo00092a017

  日期：1994.7

  Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)(3)), were found to be stable Lewis acids in water. In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde solution) was activated and the hydroxymethylation reaction of silyl enol ethers proceeded smoothly. Lanthanide triflates were also quite effective in the aldol reaction of silyl enol ethers with aldehydes in aqueous media, and water-soluble aldehydes such as acetaldehyde, acrolein, and chloroacetaldehyde could be employed for direct use. Moreover, in all these reactions, lanthanide triflates were quantitatively recovered after the reactions were completed and could be reused.