(S)-(-)-4-methyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-pentan-1-ol | 60856-86-2

• 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: (S)-(-)-4-methyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-pentan-1-ol
• CAS: 60856-86-2
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: MHBRPMNHVFZMER-VUWPPUDQSA-N

物化性质

• 沸点：
  305.3±32.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-4-methyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-pentan-1-ol 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 对甲苯磺酸 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 2-[(S)-1-(2-{2-[(S)-1-(2-Benzyloxy-ethoxymethyl)-3-methyl-butoxy]-ethoxy}-ethoxymethyl)-3-methyl-butoxy]-ethanol
  参考文献：
  名称：

  Unconventional Amphiphilic Polymers Based on Chiral Polyethylene Oxides

  摘要：

  DOI：

  10.1002/anie.199701221
• 作为产物：
  描述：

  (S)-(-)-乙基白氨酸酯 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 生成 (S)-(-)-4-methyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-pentan-1-ol
  参考文献：
  名称：

  Unconventional Amphiphilic Polymers Based on Chiral Polyethylene Oxides

  摘要：

  DOI：

  10.1002/anie.199701221

文献信息

• Synthesis of new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety
  作者：Ilona Kovács、Péter Huszthy、Ferenc Bertha、Dénes Sziebert

  DOI：10.1016/j.tetasy.2006.09.018

  日期：2006.10

  Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active dialkyl-substituted oligoethylene glycols and phosphorus oxychloride followed by mild hydrolysis of the resulting macrocyclic chlorophosphates. Pentaethylene glycols having primary hydroxyl groups gave good yields of 17-crown-6 type ethers. Pentaethylene glycols

  从光学活性的二烷基取代的低聚乙二醇和三氯氧化磷开始，制备了七个新的对映纯质子化的含磷酸二烷基氢酯的冠醚，然后将所得的大环氯磷酸酯温和水解。具有伯羟基的五乙二醇得到17-冠-6型醚的良好产率。具有仲羟基的五乙二醇以低产率产生约相同量的17-冠-6醚和开链磷酸二氢酯。四甘醇不愿与三氯氧化磷进行大环化，特别是那些含有仲羟基的聚四氟乙烯。
• Synthesis of chiral steroid CD-ring synthon from D-leucine by means of diastereotopic face selection
  作者：Takashi Takahashi、Hiroshi Okumoto、Jiro Tsuji、Nobuyuki Harada

  DOI：10.1021/jo00179a043

  日期：1984.3
• Constitutionally Asymmetric and Chiral [2]Pseudorotaxanes¹
  作者：Masumi Asakawa、Peter R. Ashton、Wayne Hayes、Henk M. Janssen、E. W. Meijer、Stephan Menzer、Dario Pasini、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1021/ja970018i

  日期：1998.2.1

  The self-assembly and characterization of a range of chiral pseudorotaxanes has been explored using chiroptical methods. The syntheses of (i) constitutionally asymmetric acyclic hydroquinone-containing polyethers and (ii) optically active hydroquinone-containing acyclic polyethers, bearing pairs of methyl or isobutyl groups related to each other in a C-2-symmetric manner within the polyether backbone, are described. The combination of (i) the tetracationic cyclophane cyclobis(paraquat-p-phenylene) tetrakis(hexafluorophosphate), possessing a pi-electron deficient cavity, and (ii) the linear noncentrosymmetric acyclic polyethers produces [2]pseudorotaxanes that have been characterized by H-1 NMR, UV/vis and circular dichroism (CD) spectroscopies in solution and by X-ray crystallography in the solid state. The introduction of constitutional asymmetry or chirality gives rise to a number of different geometries for the [2]pseudorotaxanes in both the solution and solid states. in particular, CD-spectroscopic measurements on the optically active [2]pseudorotaxanes have shown that-depending on the positions of the C-2 symmetrically related chiral centers in the polyether chains with respect to the hydroquinone rings-the chirality present in the pi-electron rich threadrike guest can induce chirality that is associated with the supramolecular structure as a whole, resulting in a chiral charge-transfer transition involving not only the pi-donors in the chiral guests but also the pi-acceptors in the achiral host.
• Enantiomerically pure chiral pyridino-crown ethers: synthesis and enantioselectivity toward the enantiomers of α-(1-naphthyl)ethylammonium perchlorate
  作者：Erika Samu、Péter Huszthy、György Horváth、Áron Szöllősy、András Neszmélyi

  DOI：10.1016/s0957-4166(99)00381-x

  日期：1999.9

  Seven new enantiomerically pure chiral pyridino-crown ethers (S,S)-4-(R,R)-10 were prepared. Three of them [(S,S)-4, (S,S)-7 and (R,R)-10] contain one, and two of them [(S,S)-5 and (S,S)-8] contain two linker chains with a terminal double bond. These linker chains were connected to the carbon atom at position 9 (opposite the pyridine moiety) of the macrocycle. The terminal double bond of the linker makes it possible to attach these ligands to silica gel to obtain chiral stationary phases (CSPs). The enantioselectivity of the new ligands toward the enantiomers of alpha-(1-naphthyl)ethylammonium perchlorate (NEA) was also determined by a titration H-1 NMR method. (C) 1999 Elsevier Science Ltd. All rights reserved.