Dimethyl (3-phenylacryloyl)phosphonate | 68204-11-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Dimethyl (3-phenylacryloyl)phosphonate
• 英文别名: 1-dimethoxyphosphoryl-3-phenylprop-2-en-1-one
• CAS: 68204-11-5
• 化学式: C₁₁H₁₃O₄P
• 分子量: 240.196
• InChiKey: UNHQSUOJOFJHRW-UHFFFAOYSA-N

物化性质

• 沸点：
  331.1±35.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl (3-phenylacryloyl)phosphonate 、 Trimethyl-(4-methylphenyl)imino-lambda5-phosphane 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  α-Ketiminophosphonates: Synthesis and Applications

  摘要：

  DOI：

  10.1080/10426507.2010.521211

文献信息

• Design and Applications of <i>N</i>-<i>tert</i>-Butyl Sulfinyl Squaramide Catalysts
  作者：Yao Li、Cyndi Qixin He、Fei-Xiang Gao、Zhen Li、Xiao-Song Xue、Xin Li、K. N. Houk、Jin-Pei Cheng

  DOI：10.1021/acs.orglett.7b00727

  日期：2017.4.7

  A new chiral HBD system, N-tert-butyl sulfinyl squaramide, was designed and synthesized. The core N-tert-butyl sulfinyl squaramide with an 1-aminoindan-2-ol skeleton was found to be an efficient catalyst in the enantioselective Friedel–Crafts alkylation of indoles and acyl phosphonates.

  一种新的手性HBD系统，ñ -叔丁基亚磺酰基squaramide，设计并合成。核心ñ -叔丁基亚磺酰基squaramide与1-氨基茚满-2-醇骨架被发现是在吲哚和酰基膦酸酯的对映选择性的Friedel-Crafts烷基化的有效催化剂。
• Dual Heterogeneous Catalysis for a Regioselective Three‐ Component Synthesis of Bi‐ and Tri(hetero)arylpyridines
  作者：Christophe Allais、Frédéric Liéby‐Muller、Thierry Constantieux、Jean Rodriguez

  DOI：10.1002/adsc.201200412

  日期：2012.9.17

  user‐friendly oxidative dual heterogeneous catalytic system capable of promoting polysubstituted pyridines as unique products from simple activated Michael acceptors, 1,3‐dicarbonyls and ammonium acetate. This metal‐free environmentally‐respectful and totally regioselective domino reaction proved to be a great strategy to access bi‐ and triaryl‐type pyridines as well as challenging bi‐ and triheteroaryl‐type

  我们设计了一种新的，用户友好的氧化双重异质催化系统，能够促进多取代吡啶作为简单活化的迈克尔受体，1,3-二羰基和乙酸铵的独特产物。事实证明，这种无金属环保且完全区域选择性的多米诺骨牌反应是在一次操作中获得双芳基和三芳基型吡啶以及具有挑战性的双杂芳基和三杂芳基型吡啶的绝佳策略。
• Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with α,β-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-γ-lactones/lactams
  作者：Lin Chen、Zhi-Jun Wu、Ming-Liang Zhang、Deng-Feng Yue、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1021/acs.joc.5b02253

  日期：2015.12.18

  Enantioselective Michael/cyclization cascade reactions of 3-hydroxyoxindoles/3-aminooxindoles with α,β-unsaturated acyl phosphonates by using a cinchonine derived squaramide as the catalyst were developed. A broad range of spirocyclic oxindole-γ-lactones/lactams could be obtained in moderate to excellent yields (up to 98%) with good to excellent diastereo- and enantioselectivities (up to >99:1 dr and

  以辛可宁衍生的方酰胺为催化剂，开发了3-羟基氧吲哚/ 3-氨基氧吲哚与α，β-不饱和酰基膦酸酯的对映选择性迈克尔/环化级联反应。在温和条件下，可以以中等至优异的收率（高达98％）获得良好的非对映和对映选择性（高达> 99：1 dr和97％ee）的各种螺环羟吲哚-γ-内酯/内酰胺类化合物。 。这项工作代表了有关α，β-不饱和酰基膦酸酯用于螺环羟吲哚的不对称结构的第一个例子。
• Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides
  作者：Lin Chen、Yong You、Ming-Liang Zhang、Jian-qiang Zhao、Jian Zuo、Xiao-Mei Zhang、Wei-Cheng Yuan、Xiao-Ying Xu

  DOI：10.1039/c5ob00317b

  日期：——

  The first Michael addition of 3-monosubstituted oxindoles to α,β-unsaturated acyl phosphonates is investigated to give 3,3′-disubstituted oxindoles with excellent results.

  第一次将3-单取代氧化吲哚加到α，β-不饱和酰基膦酸酯中进行的Michael加成反应被研究，结果表明可以获得3,3'-二取代氧化吲哚，且反应效果优异。
• Enantioselective Synthesis of Highly Functionalized Phosphonate-Substituted Pyrans or Dihydropyrans Through Asymmetric [4+2] Cycloaddition of β,γ-Unsaturated α-Ketophosphonates with Allenic Esters
  作者：Cheng-Kui Pei、Yu Jiang、Yin Wei、Min Shi

  DOI：10.1002/anie.201206958

  日期：2012.11.5

  Tell me which you want: Catalytic asymmetric [4+2] cycloadditions of β,γ‐unsaturated α‐ketophosphonates with allenic esters catalyzed by organocatalysts derived from different cinchona alkaloids have been developed, affording phosphonate‐substituted functionalized pyran and dihydropyran derivatives in excellent yields with high enantioselectivities under mild conditions. The choice of product is controlled

  告诉我你想要什么：已经开发了由不同金鸡纳生物碱衍生的有机催化剂催化的不对称[4 + 2]β，γ-不饱和α-酮膦酸酯与烯丙基酯的环加成反应，从而以优异的产率提供了膦酸酯取代的官能化吡喃和二氢吡喃衍生物。在温和条件下具有高对映选择性。产物的选择由所选催化剂的氢键特征控制。