四乙基(2-氧代-1,3-丙烷二基)二(膦酸酯) | 1475-91-8

• 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: 四乙基(2-氧代-1,3-丙烷二基)二(膦酸酯)
• 中文别名: 四乙基(1,3)-(亚丙基-2-酮)二磷羧酸酯
• 英文名称: tetraethyl (2-oxopropane-1,3-diyl)bis(phosphonate)
• 英文别名: 1,3-bis(diethoxyphosphonato)acetone；1,3-bis(diethylphosphonato)acetone；<2-Oxopropandiyl-(1,3)>-diphosphonsaeure-tetraethylester；Tetraethyl(1,3)-(propylene-2-one)bisphosphonate；1,3-bis(diethoxyphosphoryl)propan-2-one
• CAS: 1475-91-8
• 化学式: C₁₁H₂₄O₇P₂
• 分子量: 330.255
• InChiKey: BRZHGBNQWVVBNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  四乙基(2-氧代-1,3-丙烷二基)二(膦酸酯) 、 1-丁基咪唑-2-甲醛 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到(1E,4E)-1,5-bis(1-butyl-1H-imidazol-2-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Structure–Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents

  摘要：

  Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-dihereroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clinical treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles.

  DOI：

  10.1021/acs.jmedchem.5b00470
• 作为产物：
  描述：

  diethyl phosphorylpropyne 在 sodium ethanolate 作用下， 以 丙酮 为溶剂， 生成 四乙基(2-氧代-1,3-丙烷二基)二(膦酸酯)
  参考文献：
  名称：

  Normant,H.; Sturtz,G., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1965, vol. 260, p. 1984 - 1987

  摘要：

  DOI：

文献信息

• Design, synthesis, and biological evaluation of 1,9-diheteroarylnona-1,3,6,8-tetraen-5-ones as a new class of anti-prostate cancer agents
  作者：Xiaojie Zhang、Rubing Wang、German Ruiz Perez、Guanglin Chen、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.bmc.2016.08.006

  日期：2016.10

  inhibiting prostate cancer cell proliferation. It can be concluded from our data that 1,9-diarylnona-1,3,6,8-tetraen-5-one can serve as a new potential scaffold for the development of anti-prostate cancer agents and that pyridine-4-yls and quinolin-4-yl act as optimal heteroaromatic rings for the enhanced potency of this scaffold. Two of the most potent compounds, 68 and 75, effectively suppress PC-3 cell

  为了寻求更有效的化学疗法来治疗去势抵抗性前列腺癌并受到姜黄素类似物的启发，二十五个（1 E，3 E，6 E，8 E）-1,9-diarylnona-1,3,6,8通过Wittig反应，然后进行Horner-Wadsworth-Emmons反应，已成功合成了带有两个相同末端杂芳族环的-tetraen-5-ones。其中的二十三种是新化合物。WST-1细胞增殖测定法用于评估其对雄激素敏感性和雄激素敏感性人类前列腺癌细胞系的抗增殖作用。与姜黄素相比，二十五个合成化合物中有十八个具有显着改善的效能。最佳化合物78在抑制前列腺癌细胞增殖方面，β-内啡肽的活性比姜黄素高14到23倍。从我们的数据可以得出结论，1,9-二芳基壬娜-1,3,6,8-四烯基5-one可以作为开发抗前列腺癌药物和吡啶-4-基的新的潜在支架。和喹啉-4-基充当最佳杂芳环，以增强该支架的效能。两种最有效的化合物68和75通过激活细胞凋亡和将细胞周期阻滞在G
• CuI complexes containing a multidentate and conformationally flexible dibenzylidene acetone ligand (dbathiophos): Application in catalytic alkene cyclopropanation
  作者：Amanda G. Jarvis、Adrian C. Whitwood、Ian J. S. Fairlamb

  DOI：10.1039/c0dt01612h

  日期：——

  showing that the ligand backbone of dbathiophos is hemilabile, and able to adopt different 1,4-dien-3-one conformational geometries around CuI. Complexes 4 and 6 both effectively catalyse the cyclopropanation of styrene with ethyl diazoacetate at low catalyst loadings (1 mol% Cu).

  描述了基于二亚苄基丙酮核心结构的dbathiophos（1）的多齿构象柔性配体的合成和表征。配体1对阳离子和中性Cu I物种具有高亲和力。报道了三种独特的Cu I配合物（4–6），表明dbathiophos的配体骨架是半不稳定的，并且能够在Cu I周围采用不同的1,4-dien-3-one构象几何形状。配合物4和6均能有效催化环戊烷的环丙烷化苯乙烯 和 重氮乙酸乙酯 在低催化剂负载量（1摩尔％的铜）下。
• A Remarkable<i>cis</i>- and<i>trans</i>-Spanning Dibenzylidene Acetone Diphosphine Chelating Ligand (dbaphos)
  作者：Amanda G. Jarvis、Petr E. Sehnal、Somia E. Bajwa、Adrian C. Whitwood、Xiangbiao Zhang、Man Sing Cheung、Zhenyang Lin、Ian J. S. Fairlamb

  DOI：10.1002/chem.201203691

  日期：2013.5.3

  A multidentate and flexible diolefin–diphosphine ligand, based on the dibenzylidene acetone core, namely dbaphos (1), is reported herein. The ligand adopts an array of different geometries at Pt, Pd and Rh. At PtII the dbaphos ligand forms cis‐ and trans‐diphosphine complexes and can be defined as a wide‐angle spanning ligand. 1H NMR spectroscopic analysis shows that the β‐hydrogen of one olefin moiety

  本文报道了一种基于二亚苄基丙酮核的多齿柔性二烯烃-二膦配体，即dbaphos（1）。配体在Pt，Pd和Rh处采用了一系列不同的几何形状。在Pt II处，dbaphos配体形成顺式和反式二膦配合物，可以定义为广角跨越的配体。1 H NMR光谱分析表明，一个烯烃部分的β-氢与Pt II中心发生相互作用（一种无声相互作用），这受到DFT计算的支持。在Pd 0和Rh I处，dbaphos配体同时显示出烯烃和膦与金属中心的相互作用。Pd 0dbaphos的复合物是双核的，带有双膦。该配合物表现出一个烯烃部分的配位，该配位与另一个“游离”烯烃动态交换（分子内）。dbaphos的Pd 0络合物与碘苯反应生成反式-[Pd II（dbaphos）I（Ph）]。在Rh I的情况下，dbaphos配位形成膦和烯烃部分同时占据轴向和赤道位点的结构，这与相关的二齿烯烃膦配体（“ Lei”配体）相反仅占据赤道位置，而仅磷化占据轴向位置。
• <i>O</i>-Monoacyltartaric Acid Catalyzed Enantioselective Conjugate Addition of a Boronic Acid to Dienones: Application to the Synthesis of Optically Active Cyclopentenones
  作者：Masaharu Sugiura、Ryo Kinoshita、Makoto Nakajima

  DOI：10.1021/ol502526y

  日期：2014.10.3

  Enantioselective conjugate addition of styrylboronic acid to dienones was effectively catalyzed by an O-monoacyltartaric acid to afford monostyrylated products with good enantioselectivity. The RCM of the monostyrylated products using the Hoveyda–Grubbs II catalyst afforded optically active cyclopentenones, including a synthetic intermediate of the antitumor agent TEI-9826. The study shows that a diene

  苯乙烯基硼酸向二烯酮的对映选择性共轭加成反应被O-单酰基酒石酸有效催化，得到具有良好对映选择性的单苯乙烯化产物。使用Hoveyda-Grubbs II催化剂的单苯乙烯化产品的RCM提供了光学活性的环戊烯酮，包括抗肿瘤剂TEI-9826的合成中间体。研究表明，二烯添加剂（例如1,6-庚二烯或二烯丙基醚）对于RCM是必不可少的。
• An Efficient Synthesis of Dialkyl 2-Oxoalkanephosphonates and Diphenyl-2-oxoalkylphosphine Oxides from 1-Chloralkyl Ketones
  作者：Bernard Corbel、Luc Medinger、Jean Pierre Haelters、Georges Sturtz

  DOI：10.1055/s-1985-31424

  日期：——

  The synthesis of dialkyl 2-oxoalkanephosphonates and diphenyl-2-oxoalkyl-phosphine oxides, via an Arbuzov reaction of trialkyl phosphites or ethoxydiphenylphosphine with methoxycarbonylhydrazono derivatives of 1-chloroalkyl ketones followed by carbonyl deprotection, is described.

  介绍了通过三烷基亚磷酸酯或乙氧基二苯基膦与 1-氯烷基酮的甲氧基羰基肼衍生物的 Arbuzov 反应，然后进行羰基脱保护，合成 2-氧代烷基膦酸二烷基酯和 2-氧代烷基膦氧化物的过程。