ethyl dl-2-hydroxycaproate benzoxyl ester | 139698-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl dl-2-hydroxycaproate benzoxyl ester
• 英文别名: (1-Ethoxy-1-oxohexan-2-yl) benzoate；(1-ethoxy-1-oxohexan-2-yl) benzoate
• CAS: 139698-29-6
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: DBLODEVFHNRWGW-UHFFFAOYSA-N

物化性质

• 沸点：
  174-176 °C(Press: 17 Torr)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl dl-2-hydroxycaproate benzoxyl ester 在 蒽醌 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 27.0h， 以61%的产率得到1-ethoxy-5-fluoro-1-oxohexan-2-yl benzoate
  参考文献：
  名称：

  Selective fluorination of alkyl C–H bonds via photocatalysis

  摘要：

  我们报道了使用蒽醌作为光催化剂，通过与Selectfluor®进行能量转移，生成阳离子N-自由基，用于氟化未活化的C-H键。

  DOI：

  10.1039/c4cc01848f
• 作为产物：
  描述：

  DL-2-己酸乙酯 、 苯甲酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以87%的产率得到ethyl dl-2-hydroxycaproate benzoxyl ester
  参考文献：
  名称：

  Branched-chain carbohydrate lactones from a samarium(II) iodide-promoted serial deoxygenation-carbonyl addition reaction

  摘要：

  A new deoxygenation-carbonyl addition reaction mediated by samarium(II) iodide (SmI2) in THF/HMPA was examined with carbohydrate lactones and several substrates containing an alpha-alkoxy carboxylic ester. In a single reaction, these compounds were deoxygenated and subsequently coupled to several ketones by a carbonyl addition reaction. The first reactions studied simple ester and ketone adducts which were later elaborated to more complex optically active carbohydrate lactones appended to terpene ketones. Simple esters smoothly afforded beta-hydroxy carbonyl products. Fully benzoate-protected 3-deoxycarbohydrate lactones were reacted with simple ketones to produce C2-branched sugars. The attendant carbonyl addition to the least sterically hindered face of the aldonolactone provided the major products. Moderate diastereoselectivities (up to 5:1) were observed in the simple ketone products as determined by difference NOE studies. Finally, the terpene ketones, (-)-menthone or (+)-dihydrocarvone, were coupled to 3-deoxycarbohydrate lactones which gave C2-branched sugars with very high diastereoselectivities (up to 99:1).

  DOI：

  10.1021/jo00067a045

文献信息

• The conversion of α- to β-hydroxy esters by a deoxygenation/condensation reaction promoted by samarium diiodide
  作者：Eric J. Enholm、Shujun Jiang

  DOI：10.1016/s0040-4039(00)74119-0

  日期：1992.1

  A mild reaction sequence begins by transforming an alpha-hydroxy ester to an alpha-benzoate ester. Next, the alpha-benzoate ester is both reductively deoxygenated with samarium diiodide and subsequently condensed with a ketone present in the reaction mixture to afford a beta-hydroxy ester with two new alkyl appendages.