ethyl 3-methoxy-2-diethoxyphosphorylacrylate | 1227779-17-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ethyl 3-methoxy-2-diethoxyphosphorylacrylate
• 英文别名: 3-methoxy-2-diethoxyphosphorylacrylate；ethyl 2-diethoxyphosphoryl-3-methoxyacrylate；Ethyl 2-diethoxyphosphoryl-3-methoxyprop-2-enoate
• CAS: 1227779-17-0
• 化学式: C₁₀H₁₉O₆P
• 分子量: 266.231
• InChiKey: ZFULVUCIPLYXFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±42.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-methoxy-2-diethoxyphosphorylacrylate 在 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 以71%的产率得到(Z)-3-Amino-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester
  参考文献：
  名称：

  A simple and effective synthesis of activated vinylphosphonates from 3-methoxy-2-diethoxyphosphorylacrylate

  摘要：

  A facile, efficient and general one-step procedure for the synthesis of 3-substituted 2-diethoxyphosphorylacrylates from 3-methoxy-2-diethoxyphosphorylacrylate 1b and nitrogen, carbon and phosphorus nucleophiles is presented. Reaction of 1b with 3,5-dimethoxyphenol in the presence of trifluoromethanesulfonic acid yields 3-diethoxyphosphoryl-5,7-dimethoxychromen-2-one. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.108

文献信息

• A Convenient Entry to 3-Methylidenechroman-2-ones and 2-Methylidenedihydrobenzochromen-3-ones
  作者：Tomasz Janecki、Jakub Modranka、Anna Albrecht

  DOI：10.1055/s-0030-1259046

  日期：2010.12

  A simple and versatile synthesis of 3-methylidenechroman-2-ones and 2-methylidenedihydrobenzochromen-3-ones has been developed. The reaction of phenols or naphthols with 3-methoxy-2-diethoxyphosphorylacrylate gave intermediate 3-diethoxyphosphorylchromen-2-ones or 2-diethoxyphosphorylbenzo-chromen-3-ones, respectively. These compounds were employed as Michael acceptors in the reaction with Grignard reagents to yield 4-substituted 3-diethoxyphosphorylchroman-2-ones or 1-substituted 2-diethoxyphosphoryldihydrobenzochromen-3-ones. The obtained adducts were next used as Horner-Wadsworth-Emmons reagents for the olefination of formaldehyde to give the final products.

  已经开发出一种简单且多功能的合成3-甲叉基色满-2-酮和2-甲叉基二氢苯并色满-3-酮的方法。将酚或萘酚与3-甲氧基-2-二乙氧基磷酸丙烯酸酯反应，分别得到中间体3-二乙氧基磷酸色满-2-酮或2-二乙氧基磷酸苯并色满-3-酮。这些化合物作为迈克尔受体与格氏试剂反应，生成4-取代的3-二乙氧基磷酸色满-2-酮或1-取代的2-二乙氧基磷酸二氢苯并色满-3-酮。所得加合物随后用作霍纳-沃兹沃思-埃蒙斯试剂，与甲醛进行烯化反应，得到最终产物。
• Synthesis of substituted methylidenepyrimidobenzothiazolones as potential cytotoxic agents
  作者：Jakub Modranka、Anna Pietrzak、Wojciech M. Wolf、Tomasz Janecki

  DOI：10.3998/ark.5550190.p009.707

  日期：——

  Synthesis of substituted methylidenepyrimidobenzothiazolones as potential cytotoxic agents Jakub Modranka, Anna Pietrzak, Wojciech M. Wolf and Tomasz Janecki Institute of Organic Chemistry, Lodz University of Technology, Żeromskiego 116, 90‐924 Łódź, Poland Institute of General and Ecological Chemistry, Lodz University of Technology, Żeromskiego 116, 90‐924 Łódź, Poland E‐mail: [e-mail]

  合成取代的亚甲基嘧啶基苯并噻唑酮作为潜在的细胞毒性剂 Jakub Modranka、Anna Pietrzak、Wojciech M. Wolf 和 Tomasz Janecki 有机化学研究所，罗兹理工大学，Żeromskiego 116, 90-924 Łódź，波兰大学化学研究所，罗兹大学技术，Żeromskiego 116, 90-924 Łódź，波兰电子邮件：[e-mail]
• Synthesis and biological evaluation of α-methylidene-δ-lactones with 3,4-dihydrocoumarin skeleton
  作者：Jakub Modranka、Anna Albrecht、Rafał Jakubowski、Henryk Krawczyk、Marek Różalski、Urszula Krajewska、Anna Janecka、Anna Wyrębska、Barbara Różalska、Tomasz Janecki

  DOI：10.1016/j.bmc.2012.06.022

  日期：2012.8

  and various substituents at position 4 were synthesized in a three step reaction sequence. Friedel–Crafts alkylation of phenols or naphthols using ethyl 3-methoxy-2-diethoxyphosphorylacrylate in the presence of trifluoromethanesulphonic acid gave 3-diethoxyphosphorylchromen-2-ones. These compounds were employed as Michael acceptors in the reaction with Grignard reagents to give adducts which were finally

  按照三步反应顺序，合成了一系列在4位带有各种芳族基团和各种取代基的新的3-亚甲基亚苯并二氢-2-基。在三氟甲磺酸存在下，使用丙烯酸3-甲氧基-2-二乙氧基磷酰基丙烯酸酯将苯酚或萘酚进行弗里德尔-克拉夫茨烷基化反应，得到3-二乙氧基磷酰基铬-2-基。这些化合物在与格利雅试剂反应中用作迈克尔受体，以生成加合物，这些加合物最终用作霍纳-沃兹沃思-埃蒙斯试剂，用于甲醛的烯化反应。测试了所有获得的3-亚甲基苯并二氢吡喃-2-酮抗两种人白血病细胞系NALM-6和HL-60以及MCF-7乳腺癌和HT-29结肠癌腺癌的能力。几种获得的亚甲基苯并二氢呋喃酮具有IC 50的高细胞毒性活性值低于1μM，主要针对白血病和MCF-7细胞系。结构-活性关系的研究表明，附加的存在下，邻位-融合苯环和Ñ丁基或我在4个增强丙基组的活性。还对正常的人脐静脉内皮细胞（HUVEC）进行了选定的亚甲基苯并二氢吡喃酮的测试，发现色酮
• Versatile Synthesis of 4-Methylidenepyrazolidin-3-ones Using a Horner–Wadsworth–Emmons Approach
  作者：Tomasz Janecki、Jakub Modranka、Rafał Jakubowski

  DOI：10.1055/s-0033-1340071

  日期：——

  A new, versatile method for the synthesis of, so far unknown, variously substituted 4-methylidenepyrazolidin-3-ones as potential cytotoxic agents is described. Target compounds were synthesized from the corresponding 4-diethoxyphosphorylpyrazolidin-3-ones which were used as Horner-Wadsworth-Emmons reagents for the olefination of formaldehyde. 4-Phosphorylpyrazolidin-3-ones were, in turn, obtained starting from the sodium salt of ethyl 2-diethoxyphosphoryl-3-hydroxy-2-propenoate, ethyl 2-acyl-2-diethoxyphosphorylacetates, or 3-methoxy-2-diethoxyphosphorylacrylate and monosubstituted or 1,2-disubstituted hydrazines.
• Design, synthesis and cytotoxic evaluation of 4-methylidenepyrazolidin-3-ones
  作者：Jakub Modranka、Rafał Jakubowski、Marek Różalski、Urszula Krajewska、Anna Janecka、Katarzyna Gach、Dorota Pomorska、Tomasz Janecki

  DOI：10.1016/j.ejmech.2015.01.029

  日期：2015.3

  Three series of new 4-methylidenepyrazolidin-3-ones with various substitution patterns were synthesized and tested for the cytotoxic activity against two human leukemia cell lines NALM-6 and HL-60 as well as MCF-7 breast cancer cell line. Several obtained methylidenepyrazolidinones exhibited high cytotoxic activity with IC50 values below 10 mu M, mainly against HL-60 leukemia cell line and two of them, 18d,e, displayed IC50 <= 5 mu M, against all tested cell lines. Structure activity relationship studies revealed that the presence of phenyl substituents on both ring nitrogen atoms and vinyl or phenyl substituents in position 5 are crucial for high activity. Selected methylidenepyrazolidinones were also tested on normal human umbilical vein endothelial cells (HUVEC) and pyrazolidinone 18a was found to be 5-fold more toxic against HL-60 than normal cells. (C) 2015 Elsevier Masson SAS. All rights reserved.