[1,1-2H2]-1-bromopentadecane | 86419-85-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: [1,1-2H2]-1-bromopentadecane
• 英文别名: 1-bromopentadecane-1,1-d2
• CAS: 86419-85-4
• 化学式: C₁₅H₃₁Br
• 分子量: 293.299
• InChiKey: JKOTZBXSNOGCIF-DOBBINOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  16.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  [1,1-2H2]-1-bromopentadecane 在 Amberlyst 15 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Dihydroceramide Δ⁴ Desaturase Initiates Substrate Oxidation at C-4

  摘要：

  The intermolecular primary deuterium isotope effects on the individual C-H bond cleavage steps involved in dihydroceramide Delta (4) desaturation have been determined for the first time by incubating rat liver microsomes with 1:1 mixtures of nonlabeled substrate and the appropriate regiospecifically dideutelatred analogue. Analysis of the enzymatic products via gas chromatography coupled to mass spectrometry showed that the introduction of the (E) double bond between C-4 and C-5 occurs in two discrete steps: cleavage of the C-4-H bond was found to be very sensitive to isotopic substitution (k(H)/k(D) = 8.0 +/- 0 8). while a negligible isotope effect (k(H)/k(D) = 1.02 +/- 0.07) was observed for the C-5-H bond-breaking step. According to a mechanistic model that we have previously proposed, these results suggest that initial oxidation for this desaturation reaction occurs at C-4. This finding correlates nicely with the observation that 4-hydroxylated products are produced from a similar substrate by a closely related oxidative enzyme in yeast.

  DOI：

  10.1021/ja010088w
• 作为产物：
  描述：

  十五烷酸甲酯 在 lithium aluminium deuteride 、 三溴化磷 作用下， 以 乙醚 为溶剂， 生成 [1,1-2H2]-1-bromopentadecane
  参考文献：
  名称：

  The nominal butyl ester ion in the mass spectra of long-chainn-alkyl esters: A postscript

  摘要：

  Abstractn‐Octadecyl benzoate, taken as a model for long‐chain n‐alkyl carboxylates generally, loses C14H28 under electron impact to yield a product with the same elemental composition as the butyl benzoate molecular ion. This product retains quantitatively one hydrogen from C‐6, and seems to be formed as an oxygen‐protonated 4‐benzoyloxybutyl radical. It reacts further to lose H2O, in which deuterium labeling demostrates that the second hydrogen atom comes predominantly from C‐4. The intermediate reorganization, for which the driving force is presumably furnished by the instability associated with a primary radical, is pictured in terms of cyclization via bonding between the C‐4 radical site and the benzoyl carbon concerted with hydrogen migration via a 4‐membered quasicyclic transition state.

  DOI：

  10.1002/oms.1210180305