4-羟基辛酸乙酯 | 57753-66-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-羟基辛酸乙酯
• 英文名称: ethyl 4-hydroxyoctanoate
• CAS: 57753-66-9
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: CVRDXMOYGSJRGF-UHFFFAOYSA-N

物化性质

• 沸点：
  272.2±23.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)
• 保留指数：
  2014

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-羟基辛酸乙酯 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 丙位辛内酯
  参考文献：
  名称：

  迭代方法以对映体纯顺式/反经由脯氨酸催化序贯-1,3-多元醇α-Aminoxylation和醛的霍纳-沃兹沃思-埃蒙斯烯化

  摘要：

  脯氨酸催化的串联α-氨基木糖基化和醛的HWE烯化反应的迭代使用提供了简单的1,3,3-多元醇的途径。这种方法的可行性研究最初合成顺式和反1,3- -二醇和进一步延伸到SYN /顺在不对称诱导和产率的有用水平-1,3,5-三醇。羟基内酯信息素组分（2 S，3 S）-2-羟基己基环戊酮的简短合成说明了其用法。

  DOI：

  10.1021/ol900868v
• 作为产物：
  描述：

  丙位辛内酯 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 122.5h， 生成 4-羟基辛酸乙酯
  参考文献：
  名称：

  Lipase-mediated regioselective modifications of macrolactonic sophorolipids

  摘要：

  Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lipase- B (Novozyme-435) successfully deacylated the C-6' acetoxy group of natural and peracylated SLMLs. Subsequent transesterification with acylating agents (esters of fatty acids) was successful only with the C-6' deacetylated natural SLML providing an avenue to well-defined analogues of varying amphilicity. The macrolactonic motif was essential for enzymatic recognition of the sophorose rings of these complex glycolipids. In the absence of the lactonic motif, the peracylated sophorose rings are not deacylated, rather the carboxyl end of the non-lactonic forms that was preferentially transesterified. All macrolactonic derivatives were characterized by IR, H-1, C-13, H-1-H-1 and H-1-C-13 NMR spectroscopy, as well as HRMS where applicable. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.02.043

文献信息

• A Convenient Approach to Enantioenriched Cyclopropanes Bearing Electron-Withdrawing Functionalities
  作者：Henryk Krawczyk、Katarzyna Wąsek、Jacek Kędzia

  DOI：10.1055/s-0028-1088034

  日期：——

  1,2-Disubstituted cyclopropanes with different electron-withdrawing groups were accessed stereospecifically from similarly functionalized γ-hydroxy-α,β-unsaturated compounds.

  通过特定立体化学方式，从同样具有官能团的γ-羟基-α,β-不饱和化合物中，成功制备了含有不同吸电子基团的1,2-二取代环丙烷。
• Enantioselective Synthesis of <i>syn</i>/<i>anti</i>-1,3-Amino Alcohols via Proline-Catalyzed Sequential α-Aminoxylation/α-Amination and Horner−Wadsworth−Emmons Olefination of Aldehydes
  作者：Vishwajeet Jha、Nagendra B. Kondekar、Pradeep Kumar

  DOI：10.1021/ol100856u

  日期：2010.6.18

  A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential alpha-aminoxylation/alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5-phenylpentan-2-ol, is also accomplished.
• Lipase-mediated regioselective modifications of macrolactonic sophorolipids
  作者：Aliya Sembayeva、Beniam Berhane、Jason A. Carr

  DOI：10.1016/j.tet.2017.02.043

  日期：2017.4

  Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lipase- B (Novozyme-435) successfully deacylated the C-6' acetoxy group of natural and peracylated SLMLs. Subsequent transesterification with acylating agents (esters of fatty acids) was successful only with the C-6' deacetylated natural SLML providing an avenue to well-defined analogues of varying amphilicity. The macrolactonic motif was essential for enzymatic recognition of the sophorose rings of these complex glycolipids. In the absence of the lactonic motif, the peracylated sophorose rings are not deacylated, rather the carboxyl end of the non-lactonic forms that was preferentially transesterified. All macrolactonic derivatives were characterized by IR, H-1, C-13, H-1-H-1 and H-1-C-13 NMR spectroscopy, as well as HRMS where applicable. (C) 2017 Elsevier Ltd. All rights reserved.
• Iterative Approach to Enantiopure <i>syn</i>/<i>anti</i>-1,3-Polyols via Proline-Catalyzed Sequential α-Aminoxylation and Horner−Wadsworth−Emmons Olefination of Aldehydes
  作者：Nagendra B. Kondekar、Pradeep Kumar

  DOI：10.1021/ol900868v

  日期：2009.6.18

  Iterative use of proline-catalyzed tandem α-aminoxylation and HWE olefination of aldehydes provided a simple access to 1,3-polyols. The feasibility of this approach is initially studied to synthesize syn- and anti-1,3-diols and is further extended to a syn/syn-1,3,5-triol at a useful level of asymmetric induction and yield. Its usage is illustrated by the short synthesis of a hydroxylactone pheromone

  脯氨酸催化的串联α-氨基木糖基化和醛的HWE烯化反应的迭代使用提供了简单的1,3,3-多元醇的途径。这种方法的可行性研究最初合成顺式和反1,3- -二醇和进一步延伸到SYN /顺在不对称诱导和产率的有用水平-1,3,5-三醇。羟基内酯信息素组分（2 S，3 S）-2-羟基己基环戊酮的简短合成说明了其用法。