(2-氧代四氢呋喃-3-基)膦酸二乙酯 | 2907-85-9

• 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
• 中文名称: (2-氧代四氢呋喃-3-基)膦酸二乙酯
• 英文名称: 3-diethylphosphono-2-oxo-tetrahydrofuran
• 英文别名: diethyl (2-oxotetrahydrofuran-3-yl)phosphonate；diethylphosphono-2-butyrolactone；3-Diethoxyphosphoryloxolan-2-one
• CAS: 2907-85-9
• 化学式: C₈H₁₅O₅P
• 分子量: 222.178
• InChiKey: QJJICSUKZNICGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  (2-氧代四氢呋喃-3-基)膦酸二乙酯 在 双氧水 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 α-diethoxyphosphinyl-Δ^α,β-butenolide
  参考文献：
  名称：

  α-二乙氧基膦酰基-γ-丁烯内酯，一种用于合成 α,β-双官能化 γ-内酯的多功能试剂

  摘要：

  α-二乙氧基膦酰基-γ-丁烯内酯 (2) 通过 α-二乙氧基膦酰基-γ-丁内酯碳负离子的苯基硒基化和随后苯硒基残基的氧化消除以良好的收率合成。丁烯内酯 2 经历了各种亲核试剂的迈克尔加成以生成磷酰基稳定的碳负离子，其与羰基化合物反应生成 α,β-双官能化 γ-丁内酯、木脂素和 γ-丁内酯退火化合物。

  DOI：

  10.1246/cl.1986.1229
• 作为产物：
  描述：

  3-Diethoxyphosphanyloxolan-2-one 在 氧气 作用下， 生成 (2-氧代四氢呋喃-3-基)膦酸二乙酯
  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

• Group transfer polymerization with polyunsaturated esters and silyl polyenolates
  作者：Walter R. Hertler、T. V. RajanBabu、Derick W. Ovenall、Gade S. Reddy、Dotsevi Y. Sogah

  DOI：10.1021/ja00225a040

  日期：1988.8

  (S), and 3-(2,4-hexadien- l-ylidene)-4,5-dihydrofurone (6) undergo group transfer polymerization (GTP). The reaction can be initiated by silyl ketene acetals or the silyl polyenolates 10-15 as well as the allylic silane 16 in the presence of a variety of nucleophilic anion catalysts. When silyl ketene acetals are used to initiate GTP of 1-3, 5, and 6, control of AT,, is difficult, and polymers with I@"

  多不饱和单体，戊二烯酸甲酯 (1)。2-甲基戊二烯酸甲酯和乙酯（2和3）、山梨酸乙酯（4）、粘康酸乙酯（S）和3-（2,4-己二烯-1-亚基）-4,5-二氢呋喃（6）进行基团转移聚合（GTP）。在各种亲核阴离子催化剂的存在下，反应可以由甲硅烷基乙烯酮缩醛或甲硅烷基多烯醇化物 10-15 以及烯丙基硅烷 16 引发。当使用甲硅烷基乙烯酮缩醛引发 1-3、5 和 6 的 GTP 时，很难控制 AT,, 并且获得比理论值高得多的聚合物。通过以下方法实现更接近理论和低多分散性用甲硅烷基多烯醇引发。二烯单体发生区域特异性 1,4-聚合，三烯内酯 6 发生 1,6-聚合。山梨酸乙酯和粘康酸乙酯的 GTP 以 2:1 赤型和 2.1 内消旋选择性和 3.1 反式-顺式骨架双键几何结构进行。三烯内酯 6 似乎没有表现出非对映选择性，但在双键几何结构方面表现出高反式选择性。未取代的二烯醇甲硅烷基 10 和 12
• Heteroaryl-Pyrazole Derivatives as Cannabinoid CB1 Receptor Antagonists
  申请人：LEE Jinhwa

  公开号：US20080081812A1

  公开（公告）日：2008-04-03

  A heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB 1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing the inventive heteroaryl-pyrasole compounds or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.

  一种异芳基-吡唑化合物，其公式为(I)或其药用可接受盐，可作为大麻素CB1受体的反向激动剂或拮抗剂，用于预防或治疗肥胖及其相关代谢紊乱。本发明还提供了制备本发明的异芳基-吡唑化合物或其药用可接受盐的方法，包含该化合物的药物组合物，以及用于预防或治疗肥胖及其相关代谢紊乱的方法。
• Base-Catalyzed Ethanolysis of α-Diethoxyphosphoryl-γ-lactones: A Facile Synthesis of Cyclopropanecarboxylates
  作者：Henryk Krawczyk、Katarzyna Wąsek、Jacek Kędzia

  DOI：10.1055/s-2005-917116

  日期：——

  A range of alkyl- and alkenylcyclopropanecarboxylic acid ethyl esters has been stereoselectively prepared by treatment of substituted α-diethoxyphosphoryl-y-lactones with sodium ethoxide in tetrahydrofuran.

  通过在四氢呋喃中用乙醇钠处理取代的 α-二乙氧基磷酰基-y-内酯，已经立体选择性地制备了一系列烷基和烯基环丙烷羧酸乙酯。
• Tandem Michael−Wittig−Horner Reaction: One-Pot Synthesis of δ-Substituted α,β-Unsaturated Carboxylic Acid Derivatives − Application to a Concise Synthesis of (Z)- and (E)-Ochtoden-1-al
  作者：Olivier Piva、Sébastien Comesse

  DOI：10.1002/1099-0690(200007)2000:13<2417::aid-ejoc2417>3.0.co;2-x

  日期：2000.7

  A new tandem Michael−Wittig−Horner reaction has been developed to produce in high yields δ-substituted α,β-unsaturated esters, amides and lactones. The reaction has been successfully applied to a concise synthesis of (E)- and (Z)-ochtoden-1-als, components of the male sex pheromone of boll weevil from 3-methylcyclohex-2-en-1-one.

  已经开发出一种新的串联 Michael-Wittig-Horner 反应以高产率生产 δ-取代的 α,β-不饱和酯、酰胺和内酯。该反应已成功应用于从 3-methylcyclohex-2-en-1-one 合成棉铃象甲雄性信息素的 (E)- 和 (Z)-ochtoden-1-als 组分。
• Studies of the Synthesis of Diethyl Cyclopropylphosphonate and Its Thio and Seleno Analogs
  作者：Yossi Zafrani、Ravit Chen、Nissan Ashkenazi、Yoffi Segall

  DOI：10.1080/00397910701845332

  日期：2008.2.1

  cyclopropylphosphonite, followed by oxidation with sodium periodate to the corresponding phosphonate. Alternatively, diethyl cyclopropylphosphonite was reacted with elemental sulfur or selenium to give the thio and seleno analogs, respectively. The second method involves exclusive 1,3‐elimination of HBr from diethyl 3‐bromopropylphosphonate. This method can be directed to either the 1,2‐ or the 1,3‐elimination reaction

  摘要 描述了合成未取代的环丙基膦酸二乙酯的两种方法。一种方法是环丙基溴化镁与氯亚磷酸二乙酯反应生成环丙基亚膦酸二乙酯，然后用高碘酸钠氧化成相应的膦酸酯。或者，二乙基环丙基亚膦酸酯与元素硫或硒反应，分别得到硫代和硒代类似物。第二种方法涉及从 3-溴丙基膦酸二乙酯中独家 1,3-消除 HBr。该方法可用于 1,2- 或 1,3- 消除反应，根据所使用的溶剂产生丙烯基膦酸酯或环丙基膦酸酯。