α-(Diisopropoxyphosphinyl)-γ-butyrolactone

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: α-(Diisopropoxyphosphinyl)-γ-butyrolactone
• 英文别名: Diisopropyl (2-oxotetrahydrofuran-3-yl)phosphonate；3-di(propan-2-yloxy)phosphoryloxolan-2-one
• 化学式: C₁₀H₁₉O₅P
• 分子量: 250.232
• InChiKey: GNXWKOMKLPRCHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙醛 、 α-(Diisopropoxyphosphinyl)-γ-butyrolactone 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(Z)-α-propylidene-γ-butyrolactone
  参考文献：
  名称：

  Stereocontrol in Horner-Wadsworth-Emmons condensations of .alpha.-phosphono lactones with aldehydes: a synthesis of integerrinecic acid and senecic acid lactones

  摘要：

  The Homer-Wadsworth-Emmons condensations of alpha-phosphono lactones were investigated under a variety of conditions. Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly. In contrast, these phosphonates gave predominantly the Z olefins upon treatment with propionaldehyde, K2CO3, and 18-crown-6 in THF. A similar, though somewhat less-pronounced trend was observed with the six-membered ring phosphono lactone 9a. However, in its condensation with acetaldehyde the more functionalized phosphono lactone 4 gave the best E selectivity (ca. 9:1) when DBU/CH3CN was used, providing the methyl ester of integerrinecic acid lactone (5) in 77% isolated yield. When K2CO3/18-crown-6/toluene was employed in a parallel reaction, only slight selectivity for the Z isomer was observed, but the methyl ester of senecic acid lactone (6) still was obtained in 43-46% yield from the product mixture.

  DOI：

  10.1021/jo00074a023
• 作为产物：
  描述：

  在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.0h， 生成 α-(Diisopropoxyphosphinyl)-γ-butyrolactone
  参考文献：
  名称：

  Stereocontrol in Horner-Wadsworth-Emmons condensations of .alpha.-phosphono lactones with aldehydes: a synthesis of integerrinecic acid and senecic acid lactones

  摘要：

  The Homer-Wadsworth-Emmons condensations of alpha-phosphono lactones were investigated under a variety of conditions. Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly. In contrast, these phosphonates gave predominantly the Z olefins upon treatment with propionaldehyde, K2CO3, and 18-crown-6 in THF. A similar, though somewhat less-pronounced trend was observed with the six-membered ring phosphono lactone 9a. However, in its condensation with acetaldehyde the more functionalized phosphono lactone 4 gave the best E selectivity (ca. 9:1) when DBU/CH3CN was used, providing the methyl ester of integerrinecic acid lactone (5) in 77% isolated yield. When K2CO3/18-crown-6/toluene was employed in a parallel reaction, only slight selectivity for the Z isomer was observed, but the methyl ester of senecic acid lactone (6) still was obtained in 43-46% yield from the product mixture.

  DOI：

  10.1021/jo00074a023

文献信息

• NON-AQUEOUS LIQUID ELECTROLYTE, ELECTRICITY STORAGE DEVICE USING SAME, AND PHOSPHORUS COMPOUND USED THEREIN
  申请人：UBE INDUSTRIES, LTD.

  公开号：US20170275311A1

  公开（公告）日：2017-09-28

  The present invention is concerned with a nonaqueous electrolytic solution having an electrolyte salt dissolved in a nonaqueous solvent, the nonaqueous electrolytic solution containing a compound represented by the following general formula (X), in which a polar group (X) is bound to a phosphorus atom (P), and capable of improving electrochemical characteristics in a broad temperature range; an energy storage device using the same; and a novel compound. In the formula, R 10 and R 20 are each independently an organic group selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, and an aryl group having 6 to 12 carbon atoms, or a lithium atom; and X is a polar group (i) containing a —C(═O) group, a —P(═O) group, or an —S(═O) 2 group, a polar group (ii) containing a —CN group or an alkyl group having 1 to 6 carbon atoms, in which a part of hydrogen atoms is substituted with a fluorine atom, or a 4- to 7-membered ring polar group (iii) containing a —C(═O)—O— group or a —C(═O)—N— group, provided that when X is a 4- to 7-membered ring polar group (iii) containing a —C(═O)—N— group, at least one of R 10 and R 20 is a lithium atom.

  本发明涉及一种非水电解质溶液，其中电解质盐溶解在非水溶剂中，该非水电解质溶液含有以下通式（X）所代表的化合物，其中极性基（X）与磷原子（P）结合，并能够改善广泛温度范围内的电化学特性；使用该非水电解质溶液的储能装置；以及一种新化合物。在该公式中，R10和R20分别独立地是从包括具有1至8个碳原子的烷基基团、具有2至6个碳原子的烯基基团、具有3至6个碳原子的炔基基团和具有6至12个碳原子的芳基基团或锂原子中选择的有机基团；X是一个极性基（i），其中包含一个—C(═O)基团、一个—P(═O)基团或一个—S(═O)2基团，一个极性基（ii），其中包含一个—CN基团或一个具有1至6个碳原子的烷基基团，其中部分氢原子被氟原子取代，或一个4至7环极性基（iii），其中包含一个—C(═O)—O—基团或一个—C(═O)—N—基团，但当X是一个包含一个—C(═O)—N—基团的4至7环极性基（iii）时，至少一个R10和R20是锂原子。
• Stereocontrol in Horner-Wadsworth-Emmons condensations of .alpha.-phosphono lactones with aldehydes: a synthesis of integerrinecic acid and senecic acid lactones
  作者：Koo Lee、John A. Jackson、David F. Wiemer

  DOI：10.1021/jo00074a023

  日期：1993.10

  The Homer-Wadsworth-Emmons condensations of alpha-phosphono lactones were investigated under a variety of conditions. Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly. In contrast, these phosphonates gave predominantly the Z olefins upon treatment with propionaldehyde, K2CO3, and 18-crown-6 in THF. A similar, though somewhat less-pronounced trend was observed with the six-membered ring phosphono lactone 9a. However, in its condensation with acetaldehyde the more functionalized phosphono lactone 4 gave the best E selectivity (ca. 9:1) when DBU/CH3CN was used, providing the methyl ester of integerrinecic acid lactone (5) in 77% isolated yield. When K2CO3/18-crown-6/toluene was employed in a parallel reaction, only slight selectivity for the Z isomer was observed, but the methyl ester of senecic acid lactone (6) still was obtained in 43-46% yield from the product mixture.