1-iodo-11,13-dioxatetradecane | 160206-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-iodo-11,13-dioxatetradecane
• 英文别名: 1-Iodo-10-(methoxymethoxy)decane
• CAS: 160206-52-0
• 化学式: C₁₂H₂₅IO₂
• 分子量: 328.234
• InChiKey: BEZCMHZCIBOFDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  15
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-iodo-11,13-dioxatetradecane 在 盐酸 、 正丁基锂 、 甲基锂 、 氯化铵 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 正己烷 为溶剂， 反应 37.0h， 生成 <15,15,16,16,16-2H5> 11,13-hexadecadiyn-1-ol
  参考文献：
  名称：

  Synthesis of [16,16,16-2H3] 11-hexadecynoic acid and [15,15,16,16,16-2H5] (Z,Z)-11,13-hexadecadienoic acid and their use as tracers in a key step of the sex pheromone biosynthesis of the processionary moth.

  摘要：

  The synthesis of deuterium labeled 11-hexadecynoic acid and (Z,Z)-11,13-hexadecadienoic acid and their use to investigate the biosynthetic pathway of the processionary moth sex pheromone is reported. In [16,16,16-H-2(3)] 11-hexadecynoic acid, deuterium atoms were introduced by reaction of iodoalkyne 6b with (CD3)(2)CuLi. Alkylation of terminal diyne 14b with CD3CD2I followed by stereoselective reduction of the corresponding diyne to the corresponding (Z,Z) diene afforded [15,15,16,16,16-H-2(5)] (Z,Z)-11,13-hexadecadienoic acid. GLC-MS analyses of extracts from pheromone glands incubated with these tracers revealed that the acetylenic acid, but not the dienoic acid, is a precursor of the pheromone enyne system.

  DOI：

  10.1016/s0040-4020(01)85545-9
• 作为产物：
  描述：

  1-溴-10-(甲氧基甲氧基)癸烷 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 1-iodo-11,13-dioxatetradecane
  参考文献：
  名称：

  Synthesis of [16,16,16-2H3] 11-hexadecynoic acid and [15,15,16,16,16-2H5] (Z,Z)-11,13-hexadecadienoic acid and their use as tracers in a key step of the sex pheromone biosynthesis of the processionary moth.

  摘要：

  The synthesis of deuterium labeled 11-hexadecynoic acid and (Z,Z)-11,13-hexadecadienoic acid and their use to investigate the biosynthetic pathway of the processionary moth sex pheromone is reported. In [16,16,16-H-2(3)] 11-hexadecynoic acid, deuterium atoms were introduced by reaction of iodoalkyne 6b with (CD3)(2)CuLi. Alkylation of terminal diyne 14b with CD3CD2I followed by stereoselective reduction of the corresponding diyne to the corresponding (Z,Z) diene afforded [15,15,16,16,16-H-2(5)] (Z,Z)-11,13-hexadecadienoic acid. GLC-MS analyses of extracts from pheromone glands incubated with these tracers revealed that the acetylenic acid, but not the dienoic acid, is a precursor of the pheromone enyne system.

  DOI：

  10.1016/s0040-4020(01)85545-9

文献信息

• A model study on the mechanism of inhibition of fatty acyl desaturases by cyclopropene fatty acids
  作者：Jordi Quintana、Mireia Barrot、Gemma Fabrias、Francisco Camps

  DOI：10.1016/s0040-4020(98)00611-5

  日期：1998.8

  3-carboxycyclopropene or cyclopropenone derivatives, react with 1-propanethiol to give alkylthiocyclopropanes. None of the cyclopropenes and cyclopropene derivatives investigated reacted with other aminoacid chemical probes. These overall results support that inhibition of desaturases by cyclopropene fatty acids is caused by reaction of the unsaturated moiety with a cysteine residue of the enzyme active site.

  1,2-二烷基环丙烯，而不是相应的3-羧基环丙烯或环丙烯酮衍生物，与1-丙硫醇反应生成烷基硫代环丙烷。研究的环丙烯和环丙烯衍生物均未与其他氨基酸化学探针反应。这些总体结果支持环丙烯脂肪酸对去饱和酶的抑制是由不饱和部分与酶活性位点的半胱氨酸残基反应引起的。