1-(diethylphosphono)cyclohexene | 31651-16-8

• 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
• 英文名称: 1-(diethylphosphono)cyclohexene
• 英文别名: O,O-diethyl (cyclohex-1-enyl)phosphonate；diethyl cyclohex-1-en-1-ylphosphonate；diethyl cyclohex-1-enylphosphonate；1-Diethoxyphosphorylcyclohexene
• CAS: 31651-16-8
• 化学式: C₁₀H₁₉O₃P
• 分子量: 218.233
• InChiKey: LKZVEBMWBIQOFK-UHFFFAOYSA-N

物化性质

• 沸点：
  296.2±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-(diethylphosphono)cyclohexene 在 盐酸 、 sodium hydride 作用下， 反应 4.0h， 生成 trans-cyclohexane-1,2-diphosphonic acid
  参考文献：
  名称：

  Haegele, Gerhard; Peters, Ralf; Kreidler, Kay, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 83, # 1-4, p. 77 - 98

  摘要：

  DOI：
• 作为产物：
  描述：

  在 2,2,2-三氟乙醇 作用下， 生成 1-(diethylphosphono)cyclohexene
  参考文献：
  名称：

  Mesylate derivatives of .alpha.-hydroxy phosphonates. Formation of carbocations adjacent to the diethyl phosphonate group

  摘要：

  DOI：

  10.1021/ja00347a054

文献信息

• Copper‐Catalyzed C−P Cross‐Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with <i>in</i>   <i>situ</i> Halogen Exchange
  作者：Paweł Woźnicki、Marek Stankevič

  DOI：10.1002/ejoc.202100456

  日期：2021.6.25

  A protocol for copper-catalyzed halogen exchange/C−P cross-coupling between (cyclo)alkenyl/aryl bromides and secondary phosphine oxides has been developed. The addition of sodium iodide increases the yield of the cross-coupling by promoting in situ halogen exchange of organic bromides to the corresponding iodides.

  已经开发了用于（环）烯基/芳基溴化物和二级氧化膦之间的铜催化卤素交换/CP 交叉偶联的协议。碘化钠的添加通过促进有机溴化物与相应碘化物的原位卤素交换来增加交叉偶联的产率。
• Generation of α-phosphonovinyl radicals and development of a new route to highly functionalized vinylphosphonates and vinylphosphonate-incorporated carbocyclic or heterocyclic compounds via a radical trapping sequence
  作者：Takafumi Ageno、Tatsuo Okauchi、Toru Minami、Masaru Ishida

  DOI：10.1039/b416394j

  日期：——

  of synthetically useful alpha-phosphonovinyl radicals was achieved by treatment of alpha-phosphonovinyl halides with a tributyltin radical. The alpha-phosphonovinyl radicals 2a-d were trapped with electron-rich olefins and an electron-deficient olefin to produce alpha-functionalized vinylphosphonates 3a-f in 16-55% yields. The alpha-phosphonovinyl radicals 7e-g containing the YCH2CH=CH2 (Y = O, CH2,

  可通过用三丁基锡自由基处理α-膦酰乙烯基卤化物来实现合成有用的α-膦酰乙烯基自由基的第一直接产生。用富含电子的烯烃和缺电子的烯烃捕获α-膦酰基基团2a-d，以16-55％的产率产生α-官能化的乙烯基膦酸酯3a-f。在β-位含有YCH2CH = CH2（Y = O，CH2，S）取代基的α-膦酰基基团7e-g提供了5-exo和6-endo环化产物5e-g和6e-g的混合物。良品率高。5-exo / 6-endo产物比率按以下β-取代基顺序增加：OCH2CH = CH2> CH2CH2CH = CH2> SCH2CH = CH2。讨论了β-取代基对环化反应的影响。在β位上带有功能基团（例如香叶基氧基，香叶基硫基和（2-环己烯-1-基）硫基）的α-膦酰基基团的自由基环化提供了5-exo，5-exo和6-endo以及顺式稠合-5，6-环环化产物分别以良好的产率在环内结合了α，β-不饱和膦酸酯单元。对
• Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP₃ and 9anePN₂ macrocycles
  作者：Peter G. Edwards、Benson M. Kariuki、Paul D. Newman、Huw A. Tallis、Craig Williams

  DOI：10.1039/c4dt02239d

  日期：——

  Rac,trans-1,2-diphosphinocyclohexane (t-chxnP₂) has been prepared and coordinated to Cu(i), Ag(i), Fe(ii) and Mn(i) and the latter two metals used as templates for the formation of structurally reinforced 9aneP₃ and 9anePN₂ macrocycles.

  Rac，trans-1,2-二膦环己烷（t-chxnP2）已经制备并与Cu(I)，Ag(I)，Fe(II)和Mn(I)配位，并且后两种金属被用作结构加固9aneP3和9anePN2大环形成的模板。
• Phosphorylation of Alkenyl and Aryl C–O Bonds via Photoredox/Nickel Dual Catalysis
  作者：Li-Li Liao、Yong-Yuan Gui、Xiao-Bo Zhang、Guo Shen、Hui-Dong Liu、Wen-Jun Zhou、Jing Li、Da-Gang Yu

  DOI：10.1021/acs.orglett.7b01561

  日期：2017.7.21

  A phosphorylation of alkenyl and aryl C–O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are generated in moderate to excellent yields. This method features mild reaction conditions, high selectivity, good functional group tolerance, wide substrate

  据报道，在室温下，通过光氧化还原/镍双重催化使烯基和芳基C–O键发生磷酸化。通过从容易获得且廉价的磺酸盐开始，可以以中等至极好的收率生成各种重要的烯基膦酸酯和芳基膦氧化物。该方法的特点是反应条件温和，选择性高，官能团耐受性好，底物范围广，可扩展性强。
• Palladium-catalyzed New Carbon-Phosphorus Bond Formation
  作者：Toshikazu Hirao、Toshio Masunaga、Naoto Yamada、Yoshiki Ohshiro、Toshio Agawa

  DOI：10.1246/bcsj.55.909

  日期：1982.3

  Dialkyl arylphosphonates are prepared by the palladium-catalyzed reaction of aryl bromides with dialkyl phosphite in the presence of triethylamine. The similar treatment of vinyl bromides gives dialkyl vinylphosphonates stereoselectively.

  二烷基芳基膦酸酯是在三乙胺存在下通过芳基溴化物与亚磷酸二烷基酯的钯催化反应制备的。乙烯基溴化物的类似处理可立体选择性地得到乙烯基膦酸二烷基酯。