3-thexyldimethylsilyloxy-propionaldehyde | 125382-48-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-thexyldimethylsilyloxy-propionaldehyde
• 英文别名: 4-[2,3-Dimethylbutan-2-yl(dimethyl)silyl]oxybutanal
• CAS: 125382-48-1
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: IIGCQJGRIFFKND-UHFFFAOYSA-N

物化性质

• 沸点：
  259.3±23.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-thexyldimethylsilyloxy-propionaldehyde 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 作用下， 以 乙腈 为溶剂， 生成 Methyl 4-Hydroxy-6-(dimethylthexylsiloxy)hex-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction

  摘要：

  DOI：

  10.1016/s0957-4166(00)86334-x
• 作为产物：
  描述：

  二甲基叔己基氯化硅 在 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 3-thexyldimethylsilyloxy-propionaldehyde
  参考文献：
  名称：

  A new method for the synthesis of 2-carboxymethyl-2-hydroxy- tetrahydropyrans

  摘要：

  A simple synthesis of the title compounds 5 from diketene, and the aldehyde 3 is described.

  DOI：

  10.1016/s0040-4020(01)85067-5

文献信息

• Stereoselective syntheses of γ-hydroxy-α,β-unsaturated esters: An asymmetric version of the “spac” reaction
  作者：Kevin Burgess、Ian Henderson

  DOI：10.1016/s0040-4039(00)99351-1

  日期：1989.1

  Double diastereoselection in the Sulfoxide Piperidine And Carbonyl (SPAC) reactions of sulfinyl acetate esters (2) with α-unsubstituted aldehydes (3) has been investigated to facilitate asymmetric syntheses of γ-hydroxy-α,β-unsaturated esters (1).

  在双diastereoselection小号ulfoxide P -哌啶甲ND Ç氧基羰基（SPAC）亚硫酰基乙酸酯的反应（2）用α-未取代的醛（3）进行了研究，以促进γ-羟基-α，β不饱和酯的不对称合成（ 1）。
• Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog
  作者：Kevin Burgess、Juanita Cassidy、Ian Henderson

  DOI：10.1021/jo00006a017

  日期：1991.3

  Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).