Carbanion of diethyl 3,3-dimethyl-2-oxo-butanephosphonate | 68357-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: Carbanion of diethyl 3,3-dimethyl-2-oxo-butanephosphonate
• 英文别名: Carbanion of diethyl 3,3-dimethyl-2-oxobutane-phosphonate
• CAS: 68357-39-1
• 化学式: C₁₀H₂₀O₄P
• 分子量: 235.24
• InChiKey: QPCGYALEODMLJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Carbanion of diethyl 3,3-dimethyl-2-oxo-butanephosphonate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 3-(1,1,1-trifluoroprop-2-yl)-2,6,6-trimethyl-1-phenylheptane-1,5-dione
  参考文献：
  名称：

  Effect of Allylic CH_3-nF_n Groups (n = 1−3) on π-Facial Diastereoselection

  摘要：

  [GRAPHICS]Michael addition of various enolates toward gamma -CH3-nFn-alpha,beta -unsaturated ketones (n = 1-3) was proven to smoothly furnish the 1,4-adducts with high si face selectivities which monotonously decreased by reduction in the number of fluorines. Although the Felkin-Anh model correctly anticipates the present stereochemical outcome only with E-acceptors, the hyperconjugative stabilization of transition states by electron donation from the allylic substituents (the Cieplak rule) successfully explains the pi -facial preference of both acceptors at least in a qualitative level.

  DOI：

  10.1021/ol016401g
• 作为产物：
  描述：

  (3,3-二甲基-2-氧代丁基)膦酸二乙酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 Carbanion of diethyl 3,3-dimethyl-2-oxo-butanephosphonate
  参考文献：
  名称：

  Effect of Allylic CH_3-nF_n Groups (n = 1−3) on π-Facial Diastereoselection

  摘要：

  [GRAPHICS]Michael addition of various enolates toward gamma -CH3-nFn-alpha,beta -unsaturated ketones (n = 1-3) was proven to smoothly furnish the 1,4-adducts with high si face selectivities which monotonously decreased by reduction in the number of fluorines. Although the Felkin-Anh model correctly anticipates the present stereochemical outcome only with E-acceptors, the hyperconjugative stabilization of transition states by electron donation from the allylic substituents (the Cieplak rule) successfully explains the pi -facial preference of both acceptors at least in a qualitative level.

  DOI：

  10.1021/ol016401g

文献信息

• Tetrakisdehydro[14]annuleno[20]annulene
  作者：Yukihiro Yoshikawa、Masahiko Iyoda、Masazumi Nakagawa

  DOI：10.1016/s0040-4039(01)92886-2

  日期：1981.1

  Tetrakisdehydro[14]annuleno[20]annulene consisting of an aromatic bisdehydro[14]annulene and an antiaromatic trisdehydro[20]annulene has been synthesized. The 1H NHR spectra clearly indicate the induction of para- and diamagnetic ring currents in each of the [4n]- and [4n+2]-rings, respectively.

  合成了由芳香族双脱氢[14]环戊烯和抗芳族三三氢化[20]环戊烯组成的四烷基氢化[14]环戊[20]环戊烯。的1 ħNHR光谱清楚地表明对位的诱导和抗磁性环电流在每个[4N] -和[4n + 2个]型圈，分别。
• Tetrakisdehydro[16]annuleno[18]annulene
  作者：Koichi Sakano、Tsutomu Nakagawa、Masahiko Iyoda、Masazumi Nakagawa

  DOI：10.1016/s0040-4039(01)92962-4

  日期：1981.1

  consisting of trisdehydro[16]annulene and bisdehydro[18] annulene has been synthesized. Induction of para- and diamagnetic ring currents in 16- and 18-membered rings, respectively, was clearly recognized by the 1H NMR spectroscopy. A marked suppresion of the diatropicity in the 18π moiety was observed in the same trend as observed in tetrakisdehydro[14]annuleno[16]annulene.

  合成了由三去氢[16]环和双去氢[18]环组成的四氢[16]环。1 H NMR光谱清楚地识别出在16元和18元环中的顺磁环和反磁环电流的感应。观察到在18π部分的变通性显着增加，其趋势与在四烷基脱氢[14]环戊烯[16]环戊烯中观察到的趋势相同。
• TRISDEHYDRO[16]ANNULENO[18]ANNULENE
  作者：Masahiko Iyoda、Yukihiro Yoshikawa、Masazumi Nakagawa

  DOI：10.1246/cl.1982.1501

  日期：1982.10.5

  Trisdehydro[16]annuleno[18]annulene has been synthesized. A strong paratropicity was observed in the [16]annulene moiety. The observed diatropicity of the 18π moiety indicates that the 1H NMR behavior of the annulenoannulene can be regarded as a superposition of the nature of individual rings and the peripheral 4nπ-system.

  Trisdehydro[16]annuleno[18]annulene 已被合成。在 [16] 轮烯部分中观察到强烈的副向性。观察到的 18π 部分的互向性表明，环烯环烯的 1H NMR 行为可以被视为单个环和外围 4nπ 系统性质的叠加。