(R)-3-Methyl-4-<(tetrahydropyranyl)oxy>butan-1-ol | 170717-85-8

• 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: (R)-3-Methyl-4-<(tetrahydropyranyl)oxy>butan-1-ol
• 英文别名: (R)-3-methyl-4-tetrahydropyranyloxy-1-butanol；(3R)-3-methyl-4-(oxan-2-yloxy)butan-1-ol
• CAS: 170717-85-8
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: GCBSTHGWPVRNJH-YHMJZVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 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)-3-Methyl-4-<(tetrahydropyranyl)oxy>butan-1-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 22.0h， 生成 (R)-2-Methyl-1-butanol THP ether
  参考文献：
  名称：

  2-sec-Butyl-4,5-dihydrothiazole 和 (1R,5S,7R)-3,4-Dehydro-exo-brevicomin 的对映异构体的合成，雄性小鼠的信息素成分，Mus musculus

  摘要：

  已以光学活性形式合成了小鼠 Musmusculus 雄性产生的信息素的两种成分 [2-sec-butyl-4,5-dihydrothiazole (1) 和 3,4-dehydro-exo-brevicomin (2)]。1 的对映异构体以对映异构体纯度为大约 . 92% ee 并且发现容易外消旋。不对称二羟基化被用作关键反应（1516），允许制备（1R，5S，7R）-2与约。94% EE。

  DOI：

  10.1002/(sici)1099-0690(199909)1999:9<2167::aid-ejoc2167>3.0.co;2-l
• 作为产物：
  描述：

  (R)-4-羟基-3-甲基丁酸叔丁酯 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (R)-3-Methyl-4-<(tetrahydropyranyl)oxy>butan-1-ol
  参考文献：
  名称：

  2-sec-Butyl-4,5-dihydrothiazole 和 (1R,5S,7R)-3,4-Dehydro-exo-brevicomin 的对映异构体的合成，雄性小鼠的信息素成分，Mus musculus

  摘要：

  已以光学活性形式合成了小鼠 Musmusculus 雄性产生的信息素的两种成分 [2-sec-butyl-4,5-dihydrothiazole (1) 和 3,4-dehydro-exo-brevicomin (2)]。1 的对映异构体以对映异构体纯度为大约 . 92% ee 并且发现容易外消旋。不对称二羟基化被用作关键反应（1516），允许制备（1R，5S，7R）-2与约。94% EE。

  DOI：

  10.1002/(sici)1099-0690(199909)1999:9<2167::aid-ejoc2167>3.0.co;2-l

文献信息

• On the mechanism of Lewis acid promoted ene cyclizations of .omega.-unsaturated aldehydes
  作者：James A. Marshall、Marc W. Andersen

  DOI：10.1021/jo00048a016

  日期：1992.10

  The diastereomerically labeled d1 enals 1 and 2 were prepared from (S)-3-bromo-2-methylpropanol 5 by a sequence involving homologation to the allylic alcohol 13 and Sharpless epoxidation to either the alpha- or the beta-epoxide diastereomers 14 or 15. Reduction with LiAlD4 afforded the diastereomerically deuterated diols 16 and 20, respectively. Deoxygenation of the thionocarbonate derivatives 17 and 21 followed by THP ether cleavage and Swern oxidation afforded aldehydes 1 and 2. The undeuterated aldehyde 28 was similarly prepared. Cyclization of 1 and 2 with Me2AlCl afforded the cis-(E)-ethylidenecyclohexanols 3 and 4, respectively, as the major products in accord with a mechanism involving internal proton or deuteron transfer from the vinylic CHD grouping to the aldehyde carbonyl. Product ratios (E:Z, cis:trans) from the two aldehydes were significantly different, indicative of a substantial isotope effect.
• Synthesis of the Enantiomers ofanti-2,6-Dimethylheptane-1,7-diol Monotetrahydropyranyl Ether and Their Conversion into the Enantiomers of the Sex Pheromone Components of the Apple Leafminer,Lyonetia prunifoliella
  作者：Yoshihide Nakamura、Kenji Mori

  DOI：10.1002/1099-0690(200008)2000:15<2745::aid-ejoc2745>3.0.co;2-i

  日期：2000.8

  Both (2R,6R)- and (2S,6S)-isomers of 2,6-dimethylheptane-1,7-diol monotetrahydropyranyl ether (4) were synthesized, and converted into the enantiomers of anti-10,14-dimethyl-1-octadecene (1), anti-5,9-dimethyloctadecane (2) and anti-5,9-dimethylheptadecane (3), the sex pheromone components of the apple leaf miner (Lyonetia prunifoliella).
• Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, Pheromone Components of the Male Mouse,Mus musculus
  作者：Takuya Tashiro、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2167::aid-ejoc2167>3.0.co;2-l

  日期：1999.9

  Two components [2-sec-butyl-4,5-dihydrothiazole (1) and 3,4-dehydro-exo-brevicomin (2)] of a male-produced pheromone of the mouse Musmusculus have been synthesized in optically active forms. The enantiomers of 1 were obtained with an enantiomeric purity of ca. 92% ee and were found to be readily racemizable. Asymmetric dihydroxylation was employed as the key reaction (1516) allowing the preparation

  已以光学活性形式合成了小鼠 Musmusculus 雄性产生的信息素的两种成分 [2-sec-butyl-4,5-dihydrothiazole (1) 和 3,4-dehydro-exo-brevicomin (2)]。1 的对映异构体以对映异构体纯度为大约 . 92% ee 并且发现容易外消旋。不对称二羟基化被用作关键反应（1516），允许制备（1R，5S，7R）-2与约。94% EE。