(2S,3R)-(+)-methyl 2,3-dihydroxyoctanoate | 132486-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-(+)-methyl 2,3-dihydroxyoctanoate
• 英文别名: methyl syn-2,3-dihydroxyoctanoate；methyl (2S,3R)-2,3-dihydroxyoctanoate
• CAS: 132486-46-5
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: FLIBQUYKZOKSLL-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-(+)-methyl 2,3-dihydroxyoctanoate 在 palladium on activated charcoal 甲醇 、 氢溴酸 、 氢气 、 sodium acetate 作用下， 以 乙醇 为溶剂， 25.0~45.0 ℃ 、101.33 kPa 条件下， 反应 27.5h， 生成 3-羟基辛酸甲酯
  参考文献：
  名称：

  Selective transformations of threo-2,3-dihydroxy esters

  摘要：

  Two highly regio- and stereoselective transformation of threo-2,3-dihydroxy esters have been developed. In the first reaction, the alpha-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the alpha-tosylates and alpha-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield. The alpha-nosylates are also suitable electrophiles for azides, giving access to erythro-alpha-azido-beta-hydroxy esters. The second reaction involves conversion of the diol esters to acetoxy bromo esters. The beta-substituent plays a key role in determining the regiochemistry since cases with beta-alkyl substituents afford beta-acetoxy-alpha-bromo esters exclusively, whereas a beta-phenyl substituent directs formation of the alpha-acetoxy-beta-bromo ester. The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.

  DOI：

  10.1021/jo00008a051
• 作为产物：
  描述：

  反式-2-辛烯甲酯 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 96.0h， 以88%的产率得到(2S,3R)-(+)-methyl 2,3-dihydroxyoctanoate
  参考文献：
  名称：

  Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal

  摘要：

  The racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal 1, an odorant with a metallic blood smell, were synthesized. The detection threshold for humans was 0.019 ppb for (2E,4S,5S)-(-)-1 and 0.62 ppb for (2E,4R,5R)-(+)-1, respectively. The racemate (+/-)-1 made mice scared stiff at a dosage of approximately 1 mg, while the enantiomers were not significantly bioactive. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.011