1-(diethoxyphosphonyl)buta-1,3-diene | 7158-35-2

• 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: 1-(diethoxyphosphonyl)buta-1,3-diene
• 英文别名: 1-diethoxyphosphoryl-1,3-butadiene；1-diethoxyphosphorylbuta-1,3-diene；diethyl 1-phosphono-1,3-butadiene；buta-1,3-dienyl-phosphonic acid diethyl ester；Buta-1,3-dien-ξ-yl-phosphonsaeure-diaethylester；Buta-1,3-dienyl-phosphonsaeure-diaethylester
• CAS: 7158-35-2
• 化学式: C₈H₁₅O₃P
• 分子量: 190.179
• InChiKey: CIMBBEFERGFJOG-UHFFFAOYSA-N

物化性质

• 沸点：
  124-138 °C(Press: 16 Torr)
• 密度：
  1.0451 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(diethoxyphosphonyl)buta-1,3-diene 在 copper(l) chloride 作用下， 生成 4-<2-Diaethylphosphono-vinyl>-cyclohexen-1-phosphonsaeure-(3)-diaethylester
  参考文献：
  名称：

  Pudovik,A.N. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 2446 - 2449

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-diethyl (4-acetoxy-2-buten-1-yl)phosphonate 在 四(三苯基膦)钯 双硫磷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 1-(diethoxyphosphonyl)buta-1,3-diene
  参考文献：
  名称：

  Facile route to 1-phosphoryl- and 1-sulfonyl-1,3-dienes via palladium-catalyzed elimination of allylic acetates

  摘要：

  DOI：

  10.1016/s0040-4039(01)81668-3

文献信息

• Phosphonated Bicycles Bearing a N-N Junction
  作者：Jacqueline Marchand-Brynaert、Elise Villemin、Marie-France Herent

  DOI：10.3987/com-12-12653

  日期：——

  3-butadiene and cyclic azo dienophiles, such as 4-phenyl- and 4-methyl-1,2,4-triazoline-3,5- diones and phthalazine-1,4-dione gave access to phosphonated bicyclic cycloadducts bearing a N-N junction. Various functionalizations (dihydroxylation, hydrogenation and phosphonic ester deprotection) have been performed with success. The selective N-N cleavage was not possible for the preparation of large heterocycles

  二乙基 1-膦酰基-1,3-丁二烯与环状偶氮亲二烯体（例如 4-苯基和 4-甲基-1,2,4-三唑啉-3,5-二酮和 phthalazine-1）之间的 Diels-Alder 反应， 4-二酮可以得到带有 NN 结的膦酸化双环环加合物。各种官能化（二羟基化、氢化和膦酸酯脱保护）已成功进行。选择性NN裂解对于制备大杂环是不可能的。所选自行车的协调特性通过 ESI-HRMS 进行测试。© 2013 日本杂环化学研究所。
• Functionalized Phosphonated Half-Cage Molecules as Ligands for Metal Complexes
  作者：Elise Villemin、Marie-France Herent、Jacqueline Marchand-Brynaert

  DOI：10.1002/ejoc.201200806

  日期：2012.11

  additional metal coordinating groups were designed as ligands of metal cations. These compounds were synthesized by a Diels-Alder (DA) strategy, using 1-diethoxyphosphoryl-1,3-butadiene and a series of N-substituted maleimides as dienophiles. Two cycloadducts, bearing a terminal primary alcohol and a terminal iodide, respectively, were used as key intermediates for further functionalizations. Metal coordination

  具有半笼结构和带有额外金属配位基团的 N 侧链的膦化分子被设计为金属阳离子的配体。这些化合物是通过 Diels-Alder (DA) 策略合成的，使用 1-diethoxyphosphoryl-1,3-butadiene 和一系列 N-取代的马来酰亚胺作为亲二烯体。分别带有末端伯醇和末端碘化物的两种环加合物用作进一步功能化的关键中间体。ESI-HRMS 研究证明了配备有功能化 N 侧链的配体的金属配位特性。通过发射模式下的光致发光光谱测定了一种具有二膦酸化配体的选定 Eu III 复合物的化学计量
• Novel phosphonated bicyclic frameworks from Diels–Alder reaction as chelating agents of di- and trivalent metal cations
  作者：Elise Villemin、Benjamin Elias、Raphaël Robiette、Koen Robeyns、Marie-France Herent、Jean-Louis Habib-Jiwan、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.tetlet.2011.07.116

  日期：2011.10

  The synthesis of novel [4+2] cycloadducts by Diels–Alder (DA) reaction between diethyl 1-phosphono-1,3-butadiene and cyclic CC and NN dienophiles, such as maleimide and 1,2,4-triazole-3,5-dione derivatives, is described. These phosphonated bicyclic frameworks feature a cage shape enabling metal chelation. Indeed, stable complexes were formed in solution with M2+ and M3+ metal cations, as evidenced

  1-乙基膦酰基-1,3-丁二烯与环状C C和N N二烯亲核试剂如马来酰亚胺和1,2,4-三唑-之间的Diels-Alder（DA）反应合成新型[4 + 2]环加合物描述了3，5-二酮衍生物。这些膦酸化的双环骨架具有笼状形状，可实现金属螯合。实际上，如ERMS模式下的HRMS（电喷雾电离）所示，在含有M 2+和M 3+金属阳离子的溶液中形成了稳定的络合物。根据阳离子的性质，鉴定出L 1：M（一种配体一金属）和L 2：M（两种配体一金属）配合物。
• A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix
  作者：Elise Villemin、Benjamin Elias、Michel Devillers、Jacqueline Marchand-Brynaert

  DOI：10.3390/molecules18021897

  日期：——

  New host-guest materials have been prepared by incorporation of a home-made organic probe displaying a pyrene motif and a phosphonate function into a regular amphiphilic copolymer. Using powder X-Ray diffraction, photoluminescence and FT-IR spectroscopy, we have been able to study the non-covalent interactions between the host matrix and the guest molecule in the solid state. Interestingly, we have shown that the matrix directs the guest spatial localization and alters its properties. Thanks to the comparison of pyrene vs. N-pyrenylmaleimide derivatives, the influence of the chemical nature of the guest molecules on the non-covalent interactions with the host have been studied. In addition, using polyethylene glycol as a reference host, we have been able to evidence a true matrix effect within our new insertion materials. The phosphonated guest molecule appears to be a novel probe targeting the hydrophilic domain of the host copolymer.

  通过将自制的具有芘基团和膦酸盐功能的有机探针加入到规则的两亲共聚物中，我们制备出了新的主客体材料。利用粉末 X 射线衍射、光致发光和傅立叶变换红外光谱，我们研究了固态下主基质与客体分子之间的非共价相互作用。有趣的是，我们发现基质会引导客体的空间定位并改变其性质。通过比较芘和 N-芘马来酰亚胺衍生物，我们研究了客体分子的化学性质对与宿主的非共价相互作用的影响。此外，我们还使用聚乙二醇作为参考宿主，证明我们的新型插入材料具有真正的基质效应。膦化客体分子似乎是一种新型探针，其目标是宿主共聚物的亲水结构域。
• Novel chiral 1-phosphono-1,3-butadiene for asymmetric hetero Diels–Alder cycloadditions with nitroso and azodicarboxylate dienophiles
  作者：Jean-Christophe Monbaliu、Bernard Tinant、Daniel Peeters、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.tetlet.2009.12.063

  日期：2010.2

  auxiliary are potent dienes for asymmetric hetero Diels–Alder reactions. Their reactivity towards model nitroso and azodicarboxylate dienophiles has been studied by means of theoretical chemistry at the B3LYP/6-31G∗∗ level. This model, taking solvent effects into account, allowed us to identify parameters governing the stereoselectivity of this reaction. Our study emphasizes a synergy effect when increasing

  带有双环（R，R）-1,3,2-二氧杂磷杂环戊烷或（R，R）-1,3,2-二氮杂膦烷助剂是用于不对称杂Diels-Alder反应的强力二烯。通过理论化学方法研究了它们对模型亚硝基和偶氮二羧酸二亲二苯醚的反应性，其水平为B3LYP / 6-31G ∗∗。考虑到溶剂的影响，该模型使我们能够确定控制该反应的立体选择性的参数。我们的研究强调增加两个伙伴的取代基的空间位阻时的协同效应。这使我们预测了一种二烯的非对映选择性高水平。因此，我们在此说明了该二烯及其与市售的亚硝基和偶氮二羧酸二亲二烯物的环加成的方便和原始的合成。