1-methyl-3,4-dibromophospholane | 873-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 1-methyl-3,4-dibromophospholane
• 英文别名: 3,4-dibromo-1-methyl-phospholane 1-oxide；1-Methyl-phospholenoxid-3,4-dibromid, 3,4-Dibrom-1-methyl-phospholan-1-oxid；3,4-Dibrom-1-methyl-phospholan-1-oxid；1-Methyl-phospholenoxid-3,4-dibromid；3,4-Dibromo-1-methyl-1lambda~5~-phospholan-1-one；3,4-dibromo-1-methyl-1λ5-phospholane 1-oxide
• CAS: 873-15-4
• 化学式: C₅H₉Br₂OP
• 分子量: 275.908
• InChiKey: JWCMCFIGNFRZET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-3,4-dibromophospholane 在 tetraphosphorus decasulfide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 29.0h， 生成 (1R,2R,3R,6R,7S)-3,10-Dimethyl-3,10-diphospha-tricyclo[5.2.1.0^2,6]deca-4,8-diene 3,10-disulfide
  参考文献：
  名称：

  13C NMR spectra of phosphole-P(IV) dimers; ABX and AA′X13C31P coupling in some derived structures

  摘要：

  AbstractThe easily obtained dimers of phosphole oxides, sulfides and methiodides give 13C NMR spectra where carbons within three (sometimes four) bonds of each 31P nucleus are doublets of doublets and thus constitute X in an AMX spectrum. Most of the spectra have been completely interpreted with the aid of spectral measurements at two magnetic fields. Saturation of the double bonds in dimers of methylphosphole–P(IV) derivatives causes the 31P nuclei to have very similar chemical shifts, with Δν not adequately different from 3J(PP) to give first‐order coupling. When both 31P nuclei couple with a given 13C, a second‐order (ABX) 31C NMR spectrum is obtained. The presence of the effect is revealed by running the 13C NMR spectra at high magnetic field; J(AX)+J(BX) is constant at all fields, but spacing between the lines of the multiplet varies. The spectrum of the oxide, with Δν/J=1.44 for the 31P spectrum at 36.43 MHz, approaches first order character at 75 MHz; the methiodide spectrum (Δν/J=4.55) is second order at 15 MHz but clearly first order at 50 MHz, and the sulfide (Δν/J=5.6) is nearly first order at 15 MHz. [2 + 2]‐Photochemical intramolecular cyclization of the dimer oxides provides cage‐like structures where the 31P nuclei are chemically equivalent, but magnetically non‐equivalent, making the 13C signals have the characteristics of X in an AA′X coupling pattern.

  DOI：

  10.1002/mrc.1270200205
• 作为产物：
  描述：

  2,5-二氢-1-甲基-1H-磷杂环戊二烯 1-氧化物 在 溴 作用下， 以 氯仿 为溶剂， 生成 1-methyl-3,4-dibromophospholane
  参考文献：
  名称：

  二烯-膦酸二卤化物加成产物以及衍生的磷烯和磷烯氧化物的结构。

  摘要：

  DOI：

  10.1021/jo01267a020

文献信息

• Preservation of the 3-phospholene nucleus in reactions of diene-methylphosphonous dichloride adducts *
  作者：Louis D. Quin、Joan A. Peters、Claibourne E. Griffin、Myra Gordon

  DOI：10.1016/s0040-4039(01)89394-1

  日期：——
• Structure of diene-phosphonous dihalide addition products and of derived phospholenes and phospholene oxides
  作者：Louis D. Quin、Joan P. Gratz、Thomas P. Barket

  DOI：10.1021/jo01267a020

  日期：1968.3
• 13C NMR spectra of phosphole-P(IV) dimers; ABX and AA′X13C31P coupling in some derived structures
  作者：Louis D. Quin、Keith A. Mesch、Ryszard Bodalski、K. Michal Pietrusiewicz

  DOI：10.1002/mrc.1270200205

  日期：1982.10

  AbstractThe easily obtained dimers of phosphole oxides, sulfides and methiodides give 13C NMR spectra where carbons within three (sometimes four) bonds of each 31P nucleus are doublets of doublets and thus constitute X in an AMX spectrum. Most of the spectra have been completely interpreted with the aid of spectral measurements at two magnetic fields. Saturation of the double bonds in dimers of methylphosphole–P(IV) derivatives causes the 31P nuclei to have very similar chemical shifts, with Δν not adequately different from 3J(PP) to give first‐order coupling. When both 31P nuclei couple with a given 13C, a second‐order (ABX) 31C NMR spectrum is obtained. The presence of the effect is revealed by running the 13C NMR spectra at high magnetic field; J(AX)+J(BX) is constant at all fields, but spacing between the lines of the multiplet varies. The spectrum of the oxide, with Δν/J=1.44 for the 31P spectrum at 36.43 MHz, approaches first order character at 75 MHz; the methiodide spectrum (Δν/J=4.55) is second order at 15 MHz but clearly first order at 50 MHz, and the sulfide (Δν/J=5.6) is nearly first order at 15 MHz. [2 + 2]‐Photochemical intramolecular cyclization of the dimer oxides provides cage‐like structures where the 31P nuclei are chemically equivalent, but magnetically non‐equivalent, making the 13C signals have the characteristics of X in an AA′X coupling pattern.