2-Heptanone, 3-ethyl-4-hydroxy-3-methyl-, (R*,R*)- | 120501-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Heptanone, 3-ethyl-4-hydroxy-3-methyl-, (R*,R*)-
• 英文别名: 2-Heptanone, 3-ethyl-4-hydroxy-3-methyl-, (R*,S*)-；(3RS,1'SR)-3-Ethyl-4-hydroxy-3-methylheptan-2-one
• CAS: 120501-83-9；120501-84-0；132646-04-9；132646-05-0
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: CGONKADSSXWSNQ-VHSXEESVSA-N

物化性质

• 沸点：
  251.5±13.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (Z)-3-Methyl-2-(trimethylsiloxy)-2-pentene 、 正丁醛 在 四丁基氟化铵 作用下， 反应 2.0h， 生成 2-Heptanone, 3-ethyl-4-hydroxy-3-methyl-, (R*,R*)- 、 2-Heptanone, 3-ethyl-4-hydroxy-3-methyl-, (R*,R*)-
  参考文献：
  名称：

  烯醇甲硅烷基醚的氟化物催化的醛醇缩合反应的立体化学。另一个非螯合过渡态的证据

  摘要：

  DOI：

  10.1016/s0040-4039(00)86713-1

文献信息

• Simple diastereoselectivity of the aldol reaction of persubstituted enolates. Stereoselective construction of quaternary centers
  作者：Shigeru Yamago、Daisuke Machii、Eiichi Nakamura

  DOI：10.1021/jo00006a026

  日期：1991.3

  Simple diastereoselectivity of several important categories of aldol reactions of persubstituted enolates has been investigated for sterically least biased cyclic and acyclic ketone and aldehyde enolates, 1-4, and has been found to be useful for the stereoselective construction of quaternary carbon centers. The types of reactions examined involve the reaction of lithium, borinate, borate, trialkoxytitanium, trichlorotitanium, and zirconium (Cp2ZrCl) enolates, and the reactions of enol silyl ethers under high pressure, fluoride catalysis, and Lewis acid catalysis. In contrast to the less substituted metal enolates, uncatalyzed reactions of persubstituted metal enolates proceeded in a sense anticipated from the conventional Zimmerman-Traxler chair transition state (TS) model. The fluoride-catalyzed reaction of the cyclic enolate 1a showed stereoselectivity consistent with the open extended TS, while enolates 2a-4a showed anomalous behavior. The selectivity of the Lewis acid mediated aldol reaction of enol silyl ethers was found to be dependent on the Lewis acid used, and the BF3.Et2O-mediated reaction of 2a and 3a showed maximum selectivity in a sense predicted by the chair TS. The stereostructures of the aldols have been determined by single-crystal X-ray analysis or by chemical correlations.