(3R,13R)-(-)-2,2,14,14-tetramethyl-8-(2-propenyl)-5,11-dioxapentadecane-3,13-diol | 255063-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,13R)-(-)-2,2,14,14-tetramethyl-8-(2-propenyl)-5,11-dioxapentadecane-3,13-diol
• CAS: 255063-29-7
• 化学式: C₂₀H₄₀O₄
• 分子量: 344.535
• InChiKey: SIHFVLZMLFDVFT-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  24.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,6-bis[(tosyloxy)methyl]pyridine 、 (3R,13R)-(-)-2,2,14,14-tetramethyl-8-(2-propenyl)-5,11-dioxapentadecane-3,13-diol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 147.0h， 以51%的产率得到(4R,14R)-(+)-4,14-di-tert-butyl-9-(2-propenyl)-3,6,12,15-tetraoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene
  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：

  2-(R)-(+)-(tetrahydropyranyloxy)-3,3-dimethylbutanol 在 吡啶 、 Amberlite IR-120 (H⁺ form) 、 potassium tert-butylate 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 72.08h， 生成 (3R,13R)-(-)-2,2,14,14-tetramethyl-8-(2-propenyl)-5,11-dioxapentadecane-3,13-diol
  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