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(5-tert-Butyl-[1,3]dithian-2-yl)-phosphonic acid bis-(2,2,2-trifluoro-ethyl) ester | 146071-50-3

中文名称
——
中文别名
——
英文名称
(5-tert-Butyl-[1,3]dithian-2-yl)-phosphonic acid bis-(2,2,2-trifluoro-ethyl) ester
英文别名
——
(5-tert-Butyl-[1,3]dithian-2-yl)-phosphonic acid bis-(2,2,2-trifluoro-ethyl) ester化学式
CAS
146071-50-3
化学式
C12H19F6O3PS2
mdl
——
分子量
420.377
InChiKey
ACWXXLKBXLBSMU-DTORHVGOSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.76
  • 重原子数:
    24.0
  • 可旋转键数:
    5.0
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    35.53
  • 氢给体数:
    0.0
  • 氢受体数:
    5.0

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Conformational Preference in 1,3-Dithianes Containing 2-Phosphoryl, -(thiophosphoryl), and -(selenophosphoryl) groups. Chemical and Crystallographic Implications of the Nature of the Anomeric Effect
    摘要:
    The operation of the anomeric effect in all the title compounds studied was found. The magnitude of the anomeric effect was found to be larger than 10 kJ/mol. Crystallographic, spectroscopic, and thermodynamic data suggest that the n(S)-sigma*(C-P) hyperconjugative interaction is one of the factors responsible for the anomeric effect. The second interaction stabilizing the axial position of phosphorus can be P=Y...H(4 or 6) hydrogen bond formation. Some other interactions are also possible, namely sigma(C(4,6)-S)-sigma*(C(2)-P) (preferring the equatorial position of phosphorus) and sigma(C(4,6)-S)-pi(P=Y) hyperconjugations and the n(S)-n(Y) repulsions. The latter interaction was also proposed as MO counterpart of lone pair-lone pair repulsions suggested by molecular mechanics calculations. It was proved that various conformation probes can afford different equilibrium constants, if weighted average method and conformationally fixed models are applied. Most of the physical quantities are dependent on the alkyl substitution in the 1,3-dithiane ring. Thus, the relevant procedure for the selection of conformational probe was presented. Since the gamma-effect value in C-13 NMR spectra was found to be very sensitive to the position of a substituent connected with the anomeric carbon atom of 1,3-dithianes, it was applied as a conformational probe. A long range (4)J(C-P) coupling constant in the C-13 NMR spectra and P-31 spin-lattice T-1(DD) relaxation times suggest the existence of close contact(s) between a heteroatom Y(Y=O,S,Se) connected with the axial phosphorus P=Y and axial protons H(4,6) in the 1,3-dithiane ring. Crystallographic data show that the distance from Y to one of these protons is usually much smaller than to the other one and smaller than the sum of H,Y van der Waals radii. The possibility of H..Y hydrogen bond formation is discussed.
    DOI:
    10.1021/jo00086a016
  • 作为产物:
    参考文献:
    名称:
    Conformational Preference in 1,3-Dithianes Containing 2-Phosphoryl, -(thiophosphoryl), and -(selenophosphoryl) groups. Chemical and Crystallographic Implications of the Nature of the Anomeric Effect
    摘要:
    The operation of the anomeric effect in all the title compounds studied was found. The magnitude of the anomeric effect was found to be larger than 10 kJ/mol. Crystallographic, spectroscopic, and thermodynamic data suggest that the n(S)-sigma*(C-P) hyperconjugative interaction is one of the factors responsible for the anomeric effect. The second interaction stabilizing the axial position of phosphorus can be P=Y...H(4 or 6) hydrogen bond formation. Some other interactions are also possible, namely sigma(C(4,6)-S)-sigma*(C(2)-P) (preferring the equatorial position of phosphorus) and sigma(C(4,6)-S)-pi(P=Y) hyperconjugations and the n(S)-n(Y) repulsions. The latter interaction was also proposed as MO counterpart of lone pair-lone pair repulsions suggested by molecular mechanics calculations. It was proved that various conformation probes can afford different equilibrium constants, if weighted average method and conformationally fixed models are applied. Most of the physical quantities are dependent on the alkyl substitution in the 1,3-dithiane ring. Thus, the relevant procedure for the selection of conformational probe was presented. Since the gamma-effect value in C-13 NMR spectra was found to be very sensitive to the position of a substituent connected with the anomeric carbon atom of 1,3-dithianes, it was applied as a conformational probe. A long range (4)J(C-P) coupling constant in the C-13 NMR spectra and P-31 spin-lattice T-1(DD) relaxation times suggest the existence of close contact(s) between a heteroatom Y(Y=O,S,Se) connected with the axial phosphorus P=Y and axial protons H(4,6) in the 1,3-dithiane ring. Crystallographic data show that the distance from Y to one of these protons is usually much smaller than to the other one and smaller than the sum of H,Y van der Waals radii. The possibility of H..Y hydrogen bond formation is discussed.
    DOI:
    10.1021/jo00086a016
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文献信息

  • Conformational Preference in 1,3-Dithianes Containing 2-Phosphoryl, -(thiophosphoryl), and -(selenophosphoryl) groups. Chemical and Crystallographic Implications of the Nature of the Anomeric Effect
    作者:Marian Mikolajczyk、Piotr P. Graczyk、Michal W. Wieczorek
    DOI:10.1021/jo00086a016
    日期:1994.4
    The operation of the anomeric effect in all the title compounds studied was found. The magnitude of the anomeric effect was found to be larger than 10 kJ/mol. Crystallographic, spectroscopic, and thermodynamic data suggest that the n(S)-sigma*(C-P) hyperconjugative interaction is one of the factors responsible for the anomeric effect. The second interaction stabilizing the axial position of phosphorus can be P=Y...H(4 or 6) hydrogen bond formation. Some other interactions are also possible, namely sigma(C(4,6)-S)-sigma*(C(2)-P) (preferring the equatorial position of phosphorus) and sigma(C(4,6)-S)-pi(P=Y) hyperconjugations and the n(S)-n(Y) repulsions. The latter interaction was also proposed as MO counterpart of lone pair-lone pair repulsions suggested by molecular mechanics calculations. It was proved that various conformation probes can afford different equilibrium constants, if weighted average method and conformationally fixed models are applied. Most of the physical quantities are dependent on the alkyl substitution in the 1,3-dithiane ring. Thus, the relevant procedure for the selection of conformational probe was presented. Since the gamma-effect value in C-13 NMR spectra was found to be very sensitive to the position of a substituent connected with the anomeric carbon atom of 1,3-dithianes, it was applied as a conformational probe. A long range (4)J(C-P) coupling constant in the C-13 NMR spectra and P-31 spin-lattice T-1(DD) relaxation times suggest the existence of close contact(s) between a heteroatom Y(Y=O,S,Se) connected with the axial phosphorus P=Y and axial protons H(4,6) in the 1,3-dithiane ring. Crystallographic data show that the distance from Y to one of these protons is usually much smaller than to the other one and smaller than the sum of H,Y van der Waals radii. The possibility of H..Y hydrogen bond formation is discussed.
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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cnmr
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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(1-氨基丁基)磷酸 顺丙烯基磷酸 除草剂BUMINAFOS 阿仑膦酸 阻燃剂 FRC-1 铵甲基膦酸盐 钠甲基乙酰基膦酸酯 钆1,5,9-三氮杂环十二烷-N,N',N''-三(亚甲基膦酸) 钆-1,4,7-三氮杂环壬烷-N,N',N''-三(亚甲基膦酸) 重氮甲基膦酸二乙酯 辛基膦酸二丁酯 辛基膦酸 辛基-膦酸二钾盐 辛-1-烯-2-基膦酸 试剂12-Azidododecylphosphonicacid 英卡膦酸 苯胺,4-乙烯基-2-(1-甲基乙基)- 苯甲基膦酸二甲酯 苯基膦酸二甲酯 苯基膦酸二仲丁酯 苯基膦酸二乙酯 苯基膦酸二乙酯 苯基磷酸二辛酯 苯基二异辛基亚磷酸酯 苯基(1H-1,2,4-三唑-1-基)甲基膦酸二乙酯 苯丁酸,b-氨基-g-苯基- 苄基膦酸苄基乙酯 苄基亚甲基二膦酸 膦酸,[(2-乙基己基)亚氨基二(亚甲基)]二,triammonium盐(9CI) 膦酸叔丁酯乙酯 膦酸单十八烷基酯钾盐 膦酸二辛酯 膦酸二(二十一烷基)酯 膦酸,辛基-,单乙基酯 膦酸,甲基-,单(2-乙基己基)酯 膦酸,甲基-,二(苯基甲基)酯 膦酸,甲基-,2-甲氧基乙基1-甲基乙基酯 膦酸,丁基乙基酯 膦酸,[苯基[(苯基甲基)氨基]甲基]-,二甲基酯 膦酸,[[羟基(苯基甲基)氨基]苯基甲基]-,二(苯基甲基)酯 膦酸,[2-(环丙基氨基)-2-羰基乙基]-,二乙基酯 膦酸,[2-(二甲基亚肼基)丙基]-,二乙基酯,(E)- 膦酸,[1-甲基-2-(苯亚氨基)乙烯基]-,二乙基酯 膦酸,[1-(乙酰基氨基)-1-甲基乙基]-(9CI) 膦酸,[(环己基氨基)苯基甲基]-,二乙基酯 膦酸,[(二乙氧基硫膦基)(二甲氨基)甲基]- 膦酸,[(2S)-2-氨基-2-苯基乙基]-,二乙基酯 膦酸,[(1Z)-2-氨基-2-(2-噻嗯基)乙烯基]-,二乙基酯 膦酸,P-[(二乙胺基)羰基]-,二乙基酯 膦酸,(氨基二环丙基甲基)-