(10-Methyldodecyl)tetrahydropyranylether | 127914-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (10-Methyldodecyl)tetrahydropyranylether
• 英文别名: 2-[(10R)-10-methyldodecoxy]oxane
• CAS: 127914-32-3
• 化学式: C₁₈H₃₆O₂
• 分子量: 284.483
• InChiKey: BHWGBFVYBKRJQQ-QNSVNVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• 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：

  (10-Methyldodecyl)tetrahydropyranylether 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以88%的产率得到(R)-10-methyldodecanol
  参考文献：
  名称：

  Bestmann, Hans Juergen; Frighetto, Rosa T. S.; Frighetto, Nelson, Liebigs Annalen der Chemie, 1990, # 8, p. 829 - 831

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-8-(四氢吡喃氧基)辛烷 在 萘 、 lithium 作用下， 反应 1.08h， 生成 (10-Methyldodecyl)tetrahydropyranylether
  参考文献：
  名称：

  Stereospecific dehydrative alkylation of bis-sulfones: synthesis of a lesser tea tortrix pheromone

  摘要：

  The intra- and intermolecular condensation of alcohols with bis-sulfone methylenes, i.e., dehydrative alkylation, using DEAD and Ph3P proceeds stereospecifically at room temperature under essentially neutral conditions affording good to excellent yields of alkylation/annulation products.

  DOI：

  10.1021/jo00074a010

文献信息

• Preparation of the versatile chiron, (R)- and (S)-12-(tetrahydropyranyloxy)-3-methyldodecan-1-ol: application to the syntheses of methyl branched insect pheromones
  作者：S. Sankaranarayanan、A. Sharma、B. A. Kulkarni、S. Chattopadhyay

  DOI：10.1021/jo00118a047

  日期：1995.6

  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).
• Bestmann, Hans Juergen; Frighetto, Rosa T. S.; Frighetto, Nelson, Liebigs Annalen der Chemie, 1990, # 8, p. 829 - 831
  作者：Bestmann, Hans Juergen、Frighetto, Rosa T. S.、Frighetto, Nelson、Vostrowsky, Otto

  DOI：——

  日期：——
• BESTMANN, HANS JURGEN;FRIGHETTO, ROSA T. S.;FRIGHETTO, NELSON;VOSTROWSKY,+, LIEBIGS ANN. CHEM.,(1990) N, C. 829-831
  作者：BESTMANN, HANS JURGEN、FRIGHETTO, ROSA T. S.、FRIGHETTO, NELSON、VOSTROWSKY,+

  DOI：——

  日期：——
• Stereospecific dehydrative alkylation of bis-sulfones: synthesis of a lesser tea tortrix pheromone
  作者：Jurong Yu、Hyun Sung Cho、J. R. Falck

  DOI：10.1021/jo00074a010

  日期：1993.10

  The intra- and intermolecular condensation of alcohols with bis-sulfone methylenes, i.e., dehydrative alkylation, using DEAD and Ph3P proceeds stereospecifically at room temperature under essentially neutral conditions affording good to excellent yields of alkylation/annulation products.
• Chemoenzymatic synthesis of (R)-(+)-2-methylbutan-1-ol, a chiral synthon for the preparation of optically active pheromones
  作者：Shimona Geresh、Thomas J. Valiyaveettil、Yair Lavie、Arnon Shani

  DOI：10.1016/s0957-4166(97)00613-7

  日期：1998.1

  Optically active (R)-(+)-2-methylbutan-1-ol(which is not commercially available) was prepared by a chemoenzymatic synthesis, in which the key step involved a reduction catalyzed by baker's yeast. The synthon was used in the synthesis of (R)-10-methyldodecan-1-yl acetate, the chiral methyl-branched pheromone of Adoxophyes sp. (C) 1998 Elsevier Science Ltd. All rights reserved.