(-)-(3R,13R)-2,2,4,4-tetramethyl-5,8,11-trioxapentadecane-3,13-diol | 133303-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(3R,13R)-2,2,4,4-tetramethyl-5,8,11-trioxapentadecane-3,13-diol
• 英文别名: (3R,13R)-(-)-2,2,14,14-tetramethyl-5,8,11-trioxapentadecane-3,13-diol；(2R)-1-[2-[2-[(2R)-2-hydroxy-3,3-dimethylbutoxy]ethoxy]ethoxy]-3,3-dimethylbutan-2-ol
• CAS: 133303-14-7
• 化学式: C₁₆H₃₄O₅
• 分子量: 306.443
• InChiKey: UUKGYGKGIRPEOC-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(3R,13R)-2,2,4,4-tetramethyl-5,8,11-trioxapentadecane-3,13-diol 在 铂 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 219.0h， 生成 3-[[(4R,14R)-4,14-ditert-butyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-19-yl]oxy]propyl-triethoxysilane
  参考文献：
  名称：

  Enantioseparation of racemic organic ammonium perchlorates by a silica gel bound optically active di-tert-butylpyridino-18-crown-6 ligand

  摘要：

  Both enantiomers of the novel chiral di-tert-butylpyridino-18-crown-6 ligand (R,R)-7 and (S,S)-7 containing an allyloxy group on the pyridine subcyclic unit were prepared by the reaction of 4-allyloxy-2,6-pyridinedimethyl ditosylate 9 and the enantiomers of di-tert-butyl-substituted tetraethylene glycol (R,R)-8 and (S,S)-8 in the presence of a strong base. One of them, (R,R)-7, was covalently attached to silica gel, and this chiral stationary phase (CSP) separated four selected racemic organic ammonium perchlorates into their enantiomers by column chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00163-9
• 作为产物：
  描述：

  三甲基乙酰氯 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 126.0h， 生成 (-)-(3R,13R)-2,2,4,4-tetramethyl-5,8,11-trioxapentadecane-3,13-diol
  参考文献：
  名称：

  Synthesis and Enantiomer Recognition of the 18-Crown-6 Derivative Containing Two Tert-Butyl Substituents as a Chiral Barrier

  摘要：

  具有两个叔丁基取代基作为手性屏障的光学活性18-冠-6衍生物，通过使用（-）-（R）-3,3-二甲基丁烷-1,2-二醇作为手性来源制备而成，并研究了其在通过体液膜传输外消旋客体分子中的手性识别行为。

  DOI：

  10.1246/bcsj.63.3695

文献信息

• 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.
• NAEMURA, KOICHIRO;UENO, MICHI, BULL. CHEM. SOC. JAP., 63,(1990) N2, C. 3695-3697
  作者：NAEMURA, KOICHIRO、UENO, MICHI

  DOI：——

  日期：——