(2,2)D2-Octanal | 89232-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,2)D2-Octanal
• CAS: 89232-15-5
• 化学式: C₈H₁₆O
• 分子量: 130.199
• InChiKey: NUJGJRNETVAIRJ-RJSZUWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  9.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2,2)D2-Octanal 生成 (4,4)D2-2(E)-decenoic acid
  参考文献：
  名称：

  Why not be a queen? Regioselectivity in mandibular secretions of honeybee castes

  摘要：

  Both female castes of the honeybee (Apis mellifera L.) synthesize hydroxylated 2(E)-decenoic acids in their mandibular glands. Queens produce 9-hydroxy-2(E)-decenoic acid as part of their primer pheromone, while workers produce the regioisomeric 10-hydroxy acid, probably as a larval food source and an antiseptic secretion. Both workers and queens are biosynthetically competent to produce the other caste's dominant hydroxylated compound, as both isomers can be detected in queens and workers. We investigated the source of the caste-determined regioselectivity of hydroxy acid biosynthesis by investigating the production and interconversion of these compounds in isolated worker honeybee mandibular glands with specifically deuterated precursors. Gas chromatographic-mass spectroscopic identification of the labeled product indicates that octadecanoic acid is converted into 10-hydroxy-2(E)-decenoic acid with higher efficiency than either hexadecanoic or decanoic acids. 10-Hydroxydecanoic acid is readily converted into 10-hydroxy-2(E)-decenoic acid as expected in the beta-oxidation process. The saturated and unsaturated 10-hydroxy acids are oxidized to the corresponding ten carbon diacids.

  DOI：

  10.1007/bf02033805
• 作为产物：
  描述：

  正辛醛 在 吡啶 、 重水 作用下， 反应 3.0h， 生成 (2,2)D2-Octanal
  参考文献：
  名称：

  Why not be a queen? Regioselectivity in mandibular secretions of honeybee castes

  摘要：

  Both female castes of the honeybee (Apis mellifera L.) synthesize hydroxylated 2(E)-decenoic acids in their mandibular glands. Queens produce 9-hydroxy-2(E)-decenoic acid as part of their primer pheromone, while workers produce the regioisomeric 10-hydroxy acid, probably as a larval food source and an antiseptic secretion. Both workers and queens are biosynthetically competent to produce the other caste's dominant hydroxylated compound, as both isomers can be detected in queens and workers. We investigated the source of the caste-determined regioselectivity of hydroxy acid biosynthesis by investigating the production and interconversion of these compounds in isolated worker honeybee mandibular glands with specifically deuterated precursors. Gas chromatographic-mass spectroscopic identification of the labeled product indicates that octadecanoic acid is converted into 10-hydroxy-2(E)-decenoic acid with higher efficiency than either hexadecanoic or decanoic acids. 10-Hydroxydecanoic acid is readily converted into 10-hydroxy-2(E)-decenoic acid as expected in the beta-oxidation process. The saturated and unsaturated 10-hydroxy acids are oxidized to the corresponding ten carbon diacids.

  DOI：

  10.1007/bf02033805

文献信息

• Base-Catalyzed Highly Stereoselective Conversion of γ-Hydroxy-α,β-acetylenic Esters to γ-Acetoxy Dienoates
  作者：Yang Yue、Xiao-Qi Yu、Lin Pu

  DOI：10.1002/chem.200802355

  日期：2009.5.11

  A convenient route with high stereo control to γ‐acetoxy dienoates is provided by the reaction of methyl propiolate with aldehydes in the presence of ZnEt2 and N‐methylimidazole at room temperature, followed by the catalytic conversion of the resulting γ‐hydroxy‐α,β‐acetylenic esters with p‐N,N‐dimethylaminopyridine (DMAP) in acetic anhydride (see scheme).

  在室温下，在ZnEt 2和N-甲基咪唑存在下，丙酸甲酯与醛反应，然后催化生成的γ-羟基-α，可实现对γ-乙酰氧基二烯酸酯的高度立体控制的便捷途径。在乙酸酐中带有p-N，N-二甲基氨基吡啶（DMAP）的β-炔属酯（参见方案）。
• Why not be a queen? Regioselectivity in mandibular secretions of honeybee castes
  作者：E. Plettner、G. R. J. Sutherland、K. N. Slessor、M. L. Winston

  DOI：10.1007/bf02033805

  日期：1995.7

  Both female castes of the honeybee (Apis mellifera L.) synthesize hydroxylated 2(E)-decenoic acids in their mandibular glands. Queens produce 9-hydroxy-2(E)-decenoic acid as part of their primer pheromone, while workers produce the regioisomeric 10-hydroxy acid, probably as a larval food source and an antiseptic secretion. Both workers and queens are biosynthetically competent to produce the other caste's dominant hydroxylated compound, as both isomers can be detected in queens and workers. We investigated the source of the caste-determined regioselectivity of hydroxy acid biosynthesis by investigating the production and interconversion of these compounds in isolated worker honeybee mandibular glands with specifically deuterated precursors. Gas chromatographic-mass spectroscopic identification of the labeled product indicates that octadecanoic acid is converted into 10-hydroxy-2(E)-decenoic acid with higher efficiency than either hexadecanoic or decanoic acids. 10-Hydroxydecanoic acid is readily converted into 10-hydroxy-2(E)-decenoic acid as expected in the beta-oxidation process. The saturated and unsaturated 10-hydroxy acids are oxidized to the corresponding ten carbon diacids.