呋喃基磷二氯化酸酯 | 105262-70-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: 呋喃基磷二氯化酸酯
• 英文名称: Furan-2-yl phosphorodichloridate
• 英文别名: 2-dichlorophosphoryloxyfuran
• CAS: 105262-70-2
• 化学式: C₄H₃Cl₂O₃P
• 分子量: 200.946
• InChiKey: LOKMIQDONWGJBT-UHFFFAOYSA-N

物化性质

• 沸点：
  73-76 °C(Press: 9 Torr)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  呋喃基磷二氯化酸酯 、 环己胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以10%的产率得到furan-2-yl N,N,N',N'-dicyclohexylamidophosphate
  参考文献：
  名称：

  Spectroscopic and dynamic NMR study, X-ray crystallography and DFT calculations of two phosphoramidates: (C4H3O2)P(O)(Cl)C6H14N and (C4H3O2)P(O)(C6H11NH)2

  摘要：

  In recent years, research in organophosphorus compounds, particularly phosphoramidates, has attracted attention because of their many applications. In this work, we report a combined experimental and theoretical study on the molecular structure and NMR spectra of two phosphoramidates (furan-2-yl N,N-diisopro-pylamidochlorophosphate (1) and furan-2-yl N,N,N',N'-dicyclohexylamidophosphate (2)). In the NMR time scale a free rotation of the C-N/P N single bonds was observed at room temperature (298 K) while the rotation freezes below 195 K for compound 1. From dynamic NMR analysis, the activation free energy (AG(#)) for rotation of the C-N/P N bonds was calculated as 9.9 +/- 0.3 kcal mol(-1). The experimental data were reinforced by theoretical calculation using the density functional theory method B3LYP and the 6-31G(d) basis set which provided activation energy (AE(double dagger)) of 9.2 kcal mol(-1). The structures of compounds 1 and 2 were determined by single crystal X-ray diffraction method. Compound 1 is formed by a racemic mixture, whose presence was evidenced only in the structure determination by X-ray. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.04.059
• 作为产物：
  描述：

  2(5H)-呋喃酮 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 生成 呋喃基磷二氯化酸酯
  参考文献：
  名称：

  两种 nostoclide 类似物的合成和结构表征

  摘要：

  摘要 适当的醛类与由 3-benzyl-5 H-furan-2-one ( 3 ) 生成的呋喃基甲硅烷氧基二烯合成子之间的乙烯基羟醛反应得到了两种截短的内酯类似物 [化合物 ( 4 ) 和 ( 5 ) ] 2）。这些化合物通过 IR、NMR（ 1 H 和 13 C）、2D NMR 光谱实验（HMBC、HSQC 和 NOESY）、MS 光谱和 X 射线晶体学进行了全面表征。化合物(4)和(5)分别在空间群P2 1 2 1 2 1 和P2 1 /c中结晶。尽管使用 NMR 未观察到化合物 ( 5 ) 在空间上接近的氢原子之间预期的相关性，但使用 X 明确确定 ( 4 ) 和 ( 5 ) 的环外双键的立体化学分别为 Z 和 E 。 -射线晶体学。晶体内两种化合物的堆积通过非经典的分子间氢键稳定。DFT 计算（B3LYP/6-31+G* 水平）证实，与其几何异构体相比，晶体结构在气相中具有最低的能量。

  DOI：

  10.1016/j.molstruc.2006.10.014

文献信息

• Phytogrowth Activity of 3-(3-Chlorobenzyl)-5-arylidenefuran-2(5H)-ones
  作者：Luiz C.A. Barbosa、Antônio J. Demuner、Célia R. A. Maltha、Róbson R. Teixeira、Kamilla A. P. Souza、Keylla U. Bicalho

  DOI：10.1515/znb-2009-0216

  日期：2009.2.1

  Nine new 3-(3-chlorobenzyl)-5-arylidenefuran-2(5H)-ones were prepared in 20 - 87% yields by reaction of 3-(3-chlorobenzyl)furan-2(5H)-one with pertinent aldehydes. All compounds were fully characterized by IR and NMR spectroscopy as well asMS spectrometry. The phytotoxic properties of the synthesized lactones were evaluated as the ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings at 10 ppm and 100 ppm. Lactone 12, at 10 ppm, was the most active and selective, inhibiting the S. bicolor and C. sativus root growth by 70.7% and 10.7%, respectively. At 10 ppm, lactone 14 caused the larger effect on the inhibition (41.9%) of C. sativus. In general, the results indicate the influence of the benzylidene ring substitution on the phytotoxic activity

  通过对3-(3-氯苄基)呋喃-2(5H)-酮与相关醛的反应，制备了九种新的3-(3-氯苄基)-5-芳基亚氨基呋喃-2(5H)-酮，收率为20%至87%。所有化合物均通过红外和核磁共振光谱以及质谱进行了全面表征。合成的内酯的植物毒性特性通过评估其对10 ppm和100 ppm浓度下影响高粱和黄瓜幼苗生长的能力来进行。其中，10 ppm浓度下，内酯12表现出最活跃和选择性，分别抑制了高粱和黄瓜根系生长70.7%和10.7%。而在10 ppm浓度下，内酯14对黄瓜的抑制效果最大（41.9%）。总的来说，结果表明苄亚甲基环取代对植物毒性活性的影响。
• Barbosa, Luiz C. A.; Varejao, Jodieh O. S.; Petrollino, Davide, ARKIVOC, 2012, vol. 2012, # 4, p. 15 - 32
  作者：Barbosa, Luiz C. A.、Varejao, Jodieh O. S.、Petrollino, Davide、Pinheiro, Patricia F.、Demuner, Antonio J.、Maltha, Celia R. A.、Forlani, Giuseppe

  DOI：——

  日期：——
• Synthesis of 3-(4-Bromobenzyl)-5-(aryl methylene)-5<i>H</i>-furan-2-ones and Their Activity as Inhibitors of the Photosynthetic Electron Transport Chain
  作者：Luiz C. A. Barbosa、Marcelo E. Rocha、Róbson R. Teixeira、Célia R.A. Maltha、Giuseppe Forlani

  DOI：10.1021/jf072120x

  日期：2007.10.1

  A series of 12 3-(4-bromobenzyl)-5-(arylmethylene)-5H-furan-2-one lactones, designed using the naturally occurring toxin nostoclides as a lead structure, were synthesized and screened as potential inhibitors of photosynthetic electron transport. The structures were confirmed by H-1 and C-13 NMR, MS, and IR analyses. Their biological activity was evaluated both in vitro, as the ability to interfere with light-driven reduction of ferricyanide by isolated spinach chloroplast-s, and in vivo, as the capability to inhibite the oxygen production by intact Chlorella cells. Some of the compounds exhibited inhibitory properties in the micromolar range against basal and phosphorylating electron flow from water to K-3[Fe(CN)(6)], with no effect on uncoupled electron flow. Thus, they seem to behave as energy-transfer inhibitors. Although poor solubility in water may limit their effectiveness, the active derivatives could present structures to be exploited for the design of new substances endowed with herbicidal activity.
• Tetramethyldiamido phosphate directed β-lithiation of a π-excessive heterocycle; d2-synthon to 2-substituted butenolides
  作者：Jan H. Näsman、Nina Kopola、Göran Pensar

  DOI：10.1016/s0040-4039(00)84267-7

  日期：1986.1
• Synthesis, structural characterization and conformational aspects of nostoclide analogues
  作者：R.R. Teixeira、L.C.A. Barbosa、J.W.de M. Carneiro、R.S. Corrêa、J. Ellena、A.C. Doriguetto

  DOI：10.1016/j.molstruc.2008.06.019

  日期：2009.1

  The synthesis and structural analysis of a set of nostoclide analogues with potential herbicide activity is described. The influence of intra- and intermolecular hydrogen bonding, as well as other interactions on the conformation and packing of the compounds is thoroughly described using DFT calculations and single crystal X-ray diffraction analyses. All lactones exhibited the Z configuration as confirmed by NOESY experiments and by single crystal X-ray diffraction measurements. (c) 2008 Elsevier B.V. All rights reserved.