(Z)-3-chloro-2-butenyl diphosphate | 88806-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: (Z)-3-chloro-2-butenyl diphosphate
• 英文别名: [(Z)-3-chlorobut-2-enyl] phosphono hydrogen phosphate
• CAS: 88806-97-7
• 化学式: C₄H₉ClO₇P₂
• 分子量: 266.512
• InChiKey: LSDXJQWOMXJURZ-RQOWECAXSA-N

物化性质

• 沸点：
  460.0±55.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二磷酸 P-(3-甲基-3-丁烯-1-基)酯 、 (Z)-3-chloro-2-butenyl diphosphate 在 avian FPPase 、 2-巯基乙醇 、 magnesium chloride 作用下， 反应 2.0h， 生成 (E,E,Z)-11-chloro-3,7-dimethyldodeca-2,6,10-triene
  参考文献：
  名称：

  Synthesis and Evaluation of Chlorinated Substrate Analogues for Farnesyl Diphosphate Synthase

  摘要：

  Substrate analogues for isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where the C3 methyl groups were replaced by chlorine, were synthesized and evaluated as substrates for avian farnesyl diphosphate synthase (FPPase). The IPP analogue (3-ClIPP) was a cosubstrate when incubated with dimethylallyl diphosphate (DMAPP) or geranyl diphosphate (GPP) to give the corresponding chlorinated analogues of geranyl diphosphate (3-ClGPP) and farnesyl diphosphate (3-ClFPP), respectively. No products were detected in incubations of 3-ClIPP with 3-ClDMAPP. Incubation of IPP with 3-ClDMAPP gave 11-ClFPP as the sole product. Values of K(M)(3-ClIPP) (with DMAPP) and K(M)(3-ClDMAPP) (With IPP) were similar to those for [PP and DMAPP; however, values of K(cat) for both analogues were substantially lower. These results are consistent with a dissociative electrophilic alkylation mechanism where the rate-limiting step changes from heterolytic cleavage of the carbon-oxygen bond in the allylic substrate to alkylation of the double bond of the homoallylic substrate.

  DOI：

  10.1021/jo1024305
• 作为产物：
  描述：

  (Z)-1,3-二氯-2-丁烯 在 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 乙腈 为溶剂， 以45%的产率得到(Z)-3-chloro-2-butenyl diphosphate
  参考文献：
  名称：

  Synthesis and Evaluation of Chlorinated Substrate Analogues for Farnesyl Diphosphate Synthase

  摘要：

  Substrate analogues for isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where the C3 methyl groups were replaced by chlorine, were synthesized and evaluated as substrates for avian farnesyl diphosphate synthase (FPPase). The IPP analogue (3-ClIPP) was a cosubstrate when incubated with dimethylallyl diphosphate (DMAPP) or geranyl diphosphate (GPP) to give the corresponding chlorinated analogues of geranyl diphosphate (3-ClGPP) and farnesyl diphosphate (3-ClFPP), respectively. No products were detected in incubations of 3-ClIPP with 3-ClDMAPP. Incubation of IPP with 3-ClDMAPP gave 11-ClFPP as the sole product. Values of K(M)(3-ClIPP) (with DMAPP) and K(M)(3-ClDMAPP) (With IPP) were similar to those for [PP and DMAPP; however, values of K(cat) for both analogues were substantially lower. These results are consistent with a dissociative electrophilic alkylation mechanism where the rate-limiting step changes from heterolytic cleavage of the carbon-oxygen bond in the allylic substrate to alkylation of the double bond of the homoallylic substrate.

  DOI：

  10.1021/jo1024305

文献信息

• Synthesis and Evaluation of Chlorinated Substrate Analogues for Farnesyl Diphosphate Synthase
  作者：Nicole A. Heaps、C. Dale Poulter

  DOI：10.1021/jo1024305

  日期：2011.3.18

  Substrate analogues for isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where the C3 methyl groups were replaced by chlorine, were synthesized and evaluated as substrates for avian farnesyl diphosphate synthase (FPPase). The IPP analogue (3-ClIPP) was a cosubstrate when incubated with dimethylallyl diphosphate (DMAPP) or geranyl diphosphate (GPP) to give the corresponding chlorinated analogues of geranyl diphosphate (3-ClGPP) and farnesyl diphosphate (3-ClFPP), respectively. No products were detected in incubations of 3-ClIPP with 3-ClDMAPP. Incubation of IPP with 3-ClDMAPP gave 11-ClFPP as the sole product. Values of K(M)(3-ClIPP) (with DMAPP) and K(M)(3-ClDMAPP) (With IPP) were similar to those for [PP and DMAPP; however, values of K(cat) for both analogues were substantially lower. These results are consistent with a dissociative electrophilic alkylation mechanism where the rate-limiting step changes from heterolytic cleavage of the carbon-oxygen bond in the allylic substrate to alkylation of the double bond of the homoallylic substrate.