(R)-3,3-dimethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]butan-1-ol p-tosylate | 255063-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3,3-dimethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]butan-1-ol p-tosylate
• 英文别名: [(2R)-3,3-dimethyl-2-(oxan-2-yloxy)butyl] 4-methylbenzenesulfonate
• CAS: 255063-31-1
• 化学式: C₁₈H₂₈O₅S
• 分子量: 356.483
• InChiKey: KZVCFXQYOVMTBB-BHWOMJMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3,3-dimethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]butan-1-ol p-tosylate 在 Amberlite IR-120 (H⁺ form) 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以96%的产率得到(R)-(-)-(tosyloxy)-3,3-dimethyl-butan-2-ol
  参考文献：
  名称：

  Enantiomerically pure chiral pyridino-crown ethers: synthesis and enantioselectivity toward the enantiomers of α-(1-naphthyl)ethylammonium perchlorate

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00381-x
• 作为产物：
  描述：

  对甲苯磺酰氯 、 2-(R)-(+)-(tetrahydropyranyloxy)-3,3-dimethylbutanol 在 吡啶 作用下， 反应 24.0h， 以91%的产率得到(R)-3,3-dimethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]butan-1-ol p-tosylate
  参考文献：
  名称：

  Enantiomerically pure chiral pyridino-crown ethers: synthesis and enantioselectivity toward the enantiomers of α-(1-naphthyl)ethylammonium perchlorate

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00381-x

文献信息

• Compositions and methods for separating amines and amino acids from their counter-enantiomers
  申请人：——

  公开号：US20040132998A1

  公开（公告）日：2004-07-08

  Diketo- and pyridine-containing chiral crown ligands having at least two chiral bulky groups attached to two different chiral carbon atoms of the crown that are covalently bonded to or coated on suitable solid supports, and further coated by hydrophobic organic solvents are disclosed. These compositions and associated methods are characterized by selectivity of several target amine or amino acid enantiomers over their counter-enantiomers and derivatives. The composition preferably has an &agr;-value greater than or equal to 4. This allows for the separation of such enantiomers with non-chromatographic resin bed separations of three separation stages or less.

  本发明揭示了至少具有两个手性笨重基团附着在皇冠的两个不同手性碳原子上的含二酮和吡啶的手性冠配体，这些基团与适当的固体支持体共价键合或涂覆，并进一步被疏水有机溶剂涂覆。这些组合物和相关方法的特征是在它们的对映异构体和衍生物中选择性地选择几个目标胺或氨基酸对映异构体。该组合物的α值最好大于或等于4。这允许通过三个或更少的非色谱树脂床分离阶段分离这些对映异构体。
• 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.