(R)-12-(Tetrahydropyranyloxy)-3-methyldodecanol | 162899-38-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-12-(Tetrahydropyranyloxy)-3-methyldodecanol
• 英文别名: (3R)-3-methyl-12-(oxan-2-yloxy)dodecan-1-ol
• CAS: 162899-38-9
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: FBOJSAHZBLUGIC-QNSVNVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-12-(Tetrahydropyranyloxy)-3-methyldodecanol 在 甲醇 、 dimsylsodium 、 4-甲基苯磺酸吡啶 、 四丁基碘化铵 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 61.0h， 生成 (12Z,3R)-1-benzyloxy-3-methylnonacos-12-ene
  参考文献：
  名称：

  Synthesis of racemic and each enantiomer of 3-methylnonacosanol, a new plant growth regulator from Lowsonia inermis

  摘要：

  An efficient synthesis of the title compound I in racemic and enantiomeric forms has been developed starting from 10-undecenoic acid. For the enantiomeric synthesis, a lipase catalyzed acylation strategy was employed to prepare the required methyl branched chiron which was subsequently derivatized to give the enantiomers of I. The plant growth regulatory (PGR) assay of I, carried out with hypocotyl cuttings of French beans (Phaseolus vulgaris L.) in Steinberg's nutrient medium revealed appreciable activity at a concentration of 2.5 ppm. The PGR activities of the compound both in racemic and enantiomeric forms were better than 1-triacontanol, the enantiomer, (S)-I being the best test candidate. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00150-0
• 作为产物：
  描述：

  乙酸乙烯酯 、 12-(Tetrahydropyranyloxy)-3-methyldodecanol 以 异丙醚 为溶剂， 反应 5.0h， 以32.56%的产率得到(R)-12-(Tetrahydropyranyloxy)-3-methyldodecanol
  参考文献：
  名称：

  Preparation of the versatile chiron, (R)- and (S)-12-(tetrahydropyranyloxy)-3-methyldodecan-1-ol: application to the syntheses of methyl branched insect pheromones

  摘要：

  A convenient chemoenzymatic synthesis for the title methyl branched chiron has been developed starting from 10-undecenoic acid (1). Thus, 1 was converted to 1-(tetrahydropyranyloxy)-10-undecan-2-one (4) which on reaction with triethyl phosphonoacetate and subsequent functionalization led to the racemic chiron 7. This was resolved via C. rugosa lipase-catalyzed acetylation and subsequently used for the syntheses of some chiral insect pheromones. Thus, (S)-7 was mesylated, reduced with LAH and acetylated to give the pheromone (R)-10-methyldodecan-1-yl acetate (I), while its oxidation to the aldehyde 10 followed by Wittig reaction with methylenephosphorane, depyranylation, and hydrogenation gave the alcohol 12. Its tosylation, detosylation, and Hg2+-catalyzed hydration furnished (R)-10-methyltridecan-2-one (II). Likewise, Wittig reaction of (R)-10 with a suitable phosphorane and similar protocol as above afforded the alcohol 14. Its tosylate was coupled with 3-butenylmagnesium bromide to furnish pheromone (S)-14-methyloctadecene (III).

  DOI：

  10.1021/jo00118a047