phenyl-thiophosphonigsaeure-O-ethylester | 6591-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl-thiophosphonigsaeure-O-ethylester
• 英文别名: O-ethyl hydrogen phenylphosphonothioate；O-ethyl hydrogen phenylphosphonothioite；Phenylphosphonous acid ethyl ester；O-Ethyl phenylphosphinothionate；O-ethyl phenylphosphinothioate；O-ethyl phenylthiophosphonite；ethoxy-phenyl-sulfanylidene-λ5-phosphane
• CAS: 6591-08-8；135388-66-8；135388-67-9
• 化学式: C₈H₁₁OPS
• 分子量: 186.214
• InChiKey: GTUQFRRUOILDRG-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C(Press: 0.1 Torr)
• 密度：
  1.1352 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  phenyl-thiophosphonigsaeure-O-ethylester 在 氢氧化钾 、 苄基三乙基氯化铵 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 2-oxo-2-phenyl-1,2λ⁵-thiaphosphorinane
  参考文献：
  名称：

  摘要：

  A new method is developed for the synthesis of 2-substituted 2-oxo-1,2 lambda (5)-thiaphospholanes and thiaphosphorinanes (thiolphostones) on the basis of intramolecular Pishchimuka rearrangement of thiophosphonic and thiophosphinic esters with omega -chloroalkyl substituentsat the phosphorus atom. Intermediate compound in the Pishchimuka rearrangement, 2-ethyl-2-ethoxy-1,2 lambda (4)-thiaphospholanium perchlorate, was isolated.

  DOI：

  10.1023/a:1012305017592
• 作为产物：
  描述：

  3,4-dimethyl-1-phenylphosphole-1-sulfide 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 phenyl-thiophosphonigsaeure-O-ethylester
  参考文献：
  名称：

  Hussong, Rita; Heydt, Heinrich; Regitz, Manfred, Phosphorus and Sulfur and the Related Elements, 1985, vol. 25, p. 201 - 212

  摘要：

  DOI：

文献信息

• Radical Addition Reactions of Phosphorus Hydrides: Tuning the Reactivity of Phosphorus Hydrides, the Use of Microwaves and Horner–Wadsworth–Emmons-Type Reactions
  作者：Christopher M. Jessop、Andrew F. Parsons、Anne Routledge、Derek J. Irvine

  DOI：10.1002/ejoc.200500907

  日期：2006.3

  reactivity of phosphorus hydrides in radical addition reactions are compared, and the substituents on phosphorus are shown to affect the efficiency of the reactions. The change in reactivity is attributed to the different bond dissociation energies of the P–H bonds, which have been calculated. Phosphorus hydrides with particularly weak P–H bonds are shown to undergo radical additions by microwave irradiation

  比较了自由基加成反应中磷氢化物的反应性，并表明磷上的取代基会影响反应的效率。反应性的变化归因于已计算出的 P-H 键的不同键解离能。在没有常规引发剂的情况下，具有特别弱 P-H 键的磷氢化物显示出通过微波辐射进行自由基加成。这些自由基加成反应产生硫代膦酸酯、硫代膦酸酯和硫化膦，它们在 HWE 型反应中反应，得到取代的烯烃。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Organische Phosphorverbindungen XXV Darstellung und Eigenschaften von sekundären und tertiären Phosphinsulfiden
  作者：Ludwig Maier

  DOI：10.1002/hlca.19660490406

  日期：——

  Two new processes for the preparation of sec. phosphine sulfides which involve reaction of dialkylamino-dialkyl or diaryl phosphines with hydrogen sulfide, and of dialkylthionophosphonates, (RO)2P(S)H, with GRIGNARD or organolithium reagents, respectively, are described. The addition of sec. phosphine sulfides to olefins and the condensation of sec. phosphine sulfides with N-hydroxymethyldialkylamines

  准备秒的两个新过程。描述了分别涉及二烷基氨基-二烷基或二芳基膦与硫化氢和（RO）2 P（S）H的二烷基硫代膦酸酯与GRIGNARD或有机锂试剂反应的硫化膦。秒的加法。膦硫化物与烯烃的缩合反应。报道了具有N-羟甲基二烷基胺的硫化膦。叔的转换。磷化氢硫化物相应的叔。用过氧化氢很容易获得氧化膦。几种新的不对称叔叔的物理性质。列出了硫化膦和氧化物。
• Synthesis and Characterization of 5-Deoxy-3-<i>O</i>-methyl-5-<i>C</i>-[(<i>R</i>) - and (<i>S</i>)-phenylphosphinothioyl]-α- and β-D-xylopyranoses. The First Sugar Analogue Having a Phosphinothioyl Group in the Hemiacetal Ring
  作者：Hiroshi Yamamoto、Tadashi Hanaya、Nobuyuki Shigetoh、Heizan Kawamoto、Saburo Inokawa

  DOI：10.1246/cl.1987.2081

  日期：1987.10.5

  Treatment of 5-deoxy-5-iodo-1,2-O-isopropylidene-β-O-methyl-α-D-xylofuranose with ethyl phenylphosphinothioate in the presence of sodium hydride, followed by the reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, and then with 0.5 M HCl–EtOH gave the title compounds, which were characterized as the 1,2,4-O-triacetates.

  在氢化钠的存在下用苯基硫代膦酸乙酯处理 5-deoxy-5-iodo-1,2-O-isopropylidene-β-O-methyl-α-D-xylofuranose，然后用二氢双（2-甲氧基乙氧基）钠还原)铝酸盐，然后用 0.5 M HCl-EtOH 得到标题化合物，其特征为 1,2,4-O-三乙酸盐。
• Copper(I)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual “soft-soft” interaction
  作者：Yan-Bo Li、Yi Li、Liang Yin

  DOI：10.1016/j.cclet.2023.109294

  日期：2024.7

  present reaction. The first “soft-soft” interaction between copper(I) catalyst and HP(S)ROR' enables facile deprotonation to generate nucleophilic [Cu]-SPROR' species. The second one between the [Cu]-SPROR' species and -unsaturated thioamides facilitated the nucleophilic addition. Finally, both Michael adducts and ()-HP(S)PhOMe are easily converted to synthetically useful compounds.

  公开了铜(I)催化的硫代膦酸酯(HP(S)ROR')与不饱和硫代酰胺的非对映发散加成，其以通常高的非对映选择性和对映选择性构建邻位手性和手性中心。在该反应中，发生HP(S)ROR'的动力学拆分，以()-Ph-BPE作为配体加成，得到高对映选择性的()-HP(S)PhOMe。通过对照实验发现，H和P NMR实验表明的双重“软-软”相互作用在本反应中是不可或缺的。铜(I)催化剂和HP(S)ROR'之间的首次“软-软”相互作用能够轻松去质子化，生成亲核[Cu]-SPROR'物质。 [Cu]-SPROR'物质和-不饱和硫代酰胺之间的第二种促进了亲核加成。最后，迈克尔加合物和 ()-HP(S)PhOMe 都很容易转化为合成上有用的化合物。
• Pudovik, A. N.; Sobanov, A. A.; Bakhtiyarova, I. V., Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2215 - 2222
  作者：Pudovik, A. N.、Sobanov, A. A.、Bakhtiyarova, I. V.、Zimin, M. G.

  DOI：——

  日期：——