2-propenyldibromophosphine | 54566-76-6

• 分子结构分类: 有机化合物 - 有机磷化合物 - 烷基卤代膦
• 英文名称: 2-propenyldibromophosphine
• 英文别名: Allyldibromphosphin；Dibromo(prop-2-enyl)phosphane
• CAS: 54566-76-6
• 化学式: C₃H₅Br₂P
• 分子量: 231.854
• InChiKey: SIKBMQZSAVEQOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-propenyldibromophosphine 在 lithium aluminium tetrahydride 作用下， 以 various solvent(s) 为溶剂， 生成 烯丙基膦
  参考文献：
  名称：

  烯丙基锡烷对磷，砷和三卤化锑的烯丙基化。烯丙基膦，Ar烷和St啶的合成，光谱表征和量子化学研究。

  摘要：

  烯丙基三丁基锡烷与磷，砷或锑三卤化物之间的反应导致相应的烯丙基膦，rs或锑二卤化物。对于磷衍生物，仅观察到γ-区域选择，如（1-甲基-2-丙烯基）-（2e，f）或（1,1-二甲基-2-丙烯基）二卤代膦酸酯（2g，h）的形成所示）分别从巴豆基锡烷1c，c'或异戊烯基锡烷1d和PCl（3）或PBr（3）开始。在80摄氏度加热时，其中的某些膦可生成相应的热力学产物。还制备了烯丙基二氯ar氨酸3a-d，并且在室温下将动力学化合物3c，d完全重排为相应的巴豆基-（3e，e'）和异戊二烯基二氯ar啶（3f）。对于锑衍生物，即使在低温（-90摄氏度）下，观察到仅包含热力学产物的粗混合物。虽然烯丙基二卤代膦和-ar氨酸不是亲电试剂的有效烯丙基化试剂，但烯丙基二氯雌激素4a，c与苯甲醛反应生成相应的均烯丙基醇。顺式和反式产品主要是从巴豆基二氯stibines（4e，e'）开始生产的。通过用四甘醇二甲醚中的L

  DOI：

  10.1021/jo971000t
• 作为产物：
  描述：

  烯丙基三丁基锡 在 三溴化磷 作用下， 生成 2-propenyldibromophosphine
  参考文献：
  名称：

  烯丙基锡烷对磷，砷和三卤化锑的烯丙基化。烯丙基膦，Ar烷和St啶的合成，光谱表征和量子化学研究。

  摘要：

  烯丙基三丁基锡烷与磷，砷或锑三卤化物之间的反应导致相应的烯丙基膦，rs或锑二卤化物。对于磷衍生物，仅观察到γ-区域选择，如（1-甲基-2-丙烯基）-（2e，f）或（1,1-二甲基-2-丙烯基）二卤代膦酸酯（2g，h）的形成所示）分别从巴豆基锡烷1c，c'或异戊烯基锡烷1d和PCl（3）或PBr（3）开始。在80摄氏度加热时，其中的某些膦可生成相应的热力学产物。还制备了烯丙基二氯ar氨酸3a-d，并且在室温下将动力学化合物3c，d完全重排为相应的巴豆基-（3e，e'）和异戊二烯基二氯ar啶（3f）。对于锑衍生物，即使在低温（-90摄氏度）下，观察到仅包含热力学产物的粗混合物。虽然烯丙基二卤代膦和-ar氨酸不是亲电试剂的有效烯丙基化试剂，但烯丙基二氯雌激素4a，c与苯甲醛反应生成相应的均烯丙基醇。顺式和反式产品主要是从巴豆基二氯stibines（4e，e'）开始生产的。通过用四甘醇二甲醚中的L

  DOI：

  10.1021/jo971000t

文献信息

• Allylation of Phosphorus, Arsenic, and Antimony Trihalides by Allylic Stannanes. Synthesis, Spectroscopic Characterization, and Quantum Chemical Investigations of Allylic Phosphines, Arsines, and Stibines
  作者：Stéphanie Le Serre、Jean-Claude Guillemin、Tamás Karpati、László Soos、László Nyulászi、Tamás Veszprémi

  DOI：10.1021/jo971000t

  日期：1998.1.1

  efficient allylation reagents of electrophiles, allylic dichlorostibines 4a,c reacted with benzaldehyde to lead to the corresponding homoallyl alcohols. Syn and anti products were mainly produced starting from crotyldichlorostibines (4e,e'). The primary allylic phosphines 7a-f, arsines 8a-f, and stibines 9a,bhave been prepared by the chemoselective reduction of the corresponding allylic dihalophosphines

  烯丙基三丁基锡烷与磷，砷或锑三卤化物之间的反应导致相应的烯丙基膦，rs或锑二卤化物。对于磷衍生物，仅观察到γ-区域选择，如（1-甲基-2-丙烯基）-（2e，f）或（1,1-二甲基-2-丙烯基）二卤代膦酸酯（2g，h）的形成所示）分别从巴豆基锡烷1c，c'或异戊烯基锡烷1d和PCl（3）或PBr（3）开始。在80摄氏度加热时，其中的某些膦可生成相应的热力学产物。还制备了烯丙基二氯ar氨酸3a-d，并且在室温下将动力学化合物3c，d完全重排为相应的巴豆基-（3e，e'）和异戊二烯基二氯ar啶（3f）。对于锑衍生物，即使在低温（-90摄氏度）下，观察到仅包含热力学产物的粗混合物。虽然烯丙基二卤代膦和-ar氨酸不是亲电试剂的有效烯丙基化试剂，但烯丙基二氯雌激素4a，c与苯甲醛反应生成相应的均烯丙基醇。顺式和反式产品主要是从巴豆基二氯stibines（4e，e'）开始生产的。通过用四甘醇二甲醚中的L
• Structural and Conformational Properties of 2-Propenylphosphine (Allylphosphine) as Studied by Microwave Spectroscopy Supplemented by Quantum Chemical Calculations
  作者：Harald Møllendal、Jean Demaison、Jean-Claude Guillemin

  DOI：10.1021/jp0262315

  日期：2002.11.1

  The microwave spectrum of 2-propenylphosphine (allylphosphine), H2C=CH-CH2-PH2, has been investigated in the 7-26.5 and 32-58.5 GHz spectral regions at about -40 degreesC. Three conformers were assigned. All three rotamers have an anti-clinal ("skew") conformation of the C=C-C-P chain of atoms. The orientation of the phosphino group is different in the three conformers denoted conformer I, II, and III, respectively. A distinction between the three forms can be made with reference to the lone pair (1p) of the phosphino group. In conformer I, the 1p-P-C-C link is anti-periplanar, whereas the 1p-P-C-C, chain is -syn-clinal ("+gauche") in conformer II and +syn-clinal ("-gauche") in conformer III. Conformer I is 1.4(3) kJ/mol more stable than II and 1.6(3) kJ/mol more stable than III. The dipole moment of conformer I was determined to be in units of 10(-30) Cm (note units): mu(a) = 2.544(14), mu(b) 0.503(25), mu(c), = 0.438(24), and mu(tot) = 2.630(20) [mu(tot) = 0.788(6) D]. The dipole moment of conformer II is mu(a) = 1.215(11), mu(b) = 3.14(12), mu(c) = 1.25(49), and mu(tot) = 3.59(31) [mu(tot) = 1.08(9) D], and the dipole moment of conformer III is mu(a) = 1.567(13), mu(b) = 2.090(21), mu(c) = 1.877(15), and mu(tot) = 3.59(31) [mu(tot) = 0.964(7) D]. Five vibrationally excited states were assigned for conformer 1, whereas two excited states were assigned for 11 as well as one for conformer III. Their vibrational frequencies were determined by relative intensity measurements. Quantum chemical calculations at the B3LYP and MP2 levels of theory reproduced the experimental rotational constants to within a few percent. Much poorer agreement is found for the components of the dipole moments (but the total dipole moment is well reproduced) as well as for the quartic centrifugal distortion constants, the error being mainly systematic in this latter case. The energy differences between the three conformers were calculated both at the Gaussian-2 and at the complete basis set levels of theory with results that are close to the experimental values.