2-[(1S)-2-[[2,5-dimethoxy-3-[[(2S)-2-(oxan-2-yloxy)-2-phenylethoxy]methyl]phenyl]methoxy]-1-phenylethoxy]oxane | 199991-84-9

• 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: 2-[(1S)-2-[[2,5-dimethoxy-3-[[(2S)-2-(oxan-2-yloxy)-2-phenylethoxy]methyl]phenyl]methoxy]-1-phenylethoxy]oxane
• CAS: 199991-84-9
• 化学式: C₃₆H₄₆O₈
• 分子量: 606.756
• InChiKey: ZBFXHCFXVGTEOM-MIXHAXSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-[(1S)-2-[[2,5-dimethoxy-3-[[(2S)-2-(oxan-2-yloxy)-2-phenylethoxy]methyl]phenyl]methoxy]-1-phenylethoxy]oxane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以65%的产率得到(1S)-2-[[3-[[(2S)-2-hydroxy-2-phenylethoxy]methyl]-2,5-dimethoxyphenyl]methoxy]-1-phenylethanol
  参考文献：
  名称：

  Preparation of optically active azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: temperature-dependent enantiomer selectivity in the complexation with chiral amines 1

  摘要：

  采用(2S,4S)-2,4-二甲基-3-氧戊烷-1,5-二醇和(S)-或(R)-1-苯乙烷-1,2-二醇作为手性子单元，合成了具有两个苯基和两个甲基取代基以及p-(2,4-二硝基苯基偶氮)酚基团的光学活性偶氮酚类冠醚(S,S,S,S)-1、(R,S,S,R)-2、(S,S,S,S)-3和(R,S,S,R)-4，并且这些化合物以对映体纯形式制备。通过在氯仿中采用紫外-可见光光谱法研究了这些冠醚与手性胺的复合过程中温度依赖的对映选择性，并根据观察到的结合常数计算了复合的热力学参数。

  DOI：

  10.1039/a703452k
• 作为产物：
  描述：

  1,3-bis-bromomethyl-2,5-dimethoxy-benzene 、 (S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到2-[(1S)-2-[[2,5-dimethoxy-3-[[(2S)-2-(oxan-2-yloxy)-2-phenylethoxy]methyl]phenyl]methoxy]-1-phenylethoxy]oxane
  参考文献：
  名称：

  Preparation of optically active azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: temperature-dependent enantiomer selectivity in the complexation with chiral amines 1

  摘要：

  采用(2S,4S)-2,4-二甲基-3-氧戊烷-1,5-二醇和(S)-或(R)-1-苯乙烷-1,2-二醇作为手性子单元，合成了具有两个苯基和两个甲基取代基以及p-(2,4-二硝基苯基偶氮)酚基团的光学活性偶氮酚类冠醚(S,S,S,S)-1、(R,S,S,R)-2、(S,S,S,S)-3和(R,S,S,R)-4，并且这些化合物以对映体纯形式制备。通过在氯仿中采用紫外-可见光光谱法研究了这些冠醚与手性胺的复合过程中温度依赖的对映选择性，并根据观察到的结合常数计算了复合的热力学参数。

  DOI：

  10.1039/a703452k

文献信息

• Preparation of homochiral azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: Enantiomer recognition behaviour towards chiral 2-aminoethanol derivatives
  作者：Koichiro Naemura、Kazuko Ogasahara、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/s0957-4166(96)00472-7

  日期：1997.1

  Enantiomerically pure azophenolic crown ethers 1–4 containing (S)- or (R)-1-phenylethane-1,2-diol moieties and (2S,4S)-2,4-dimethyl-3-oxapentane-1,5-diol moiety as a chiral subunit were prepared; crown ethers (S,S,S,S)-1 showed high chiral recognition behaviour in complexation with 2-substituted 2-aminoethanol derivatives.

  对映体纯的偶氮酚冠醚1-4，含有（S）-或（R）-1-苯基乙烷-1,2-二醇部分和（2 S，4 S）-2,4-二甲基-3-氧杂戊烷-1,5制备了作为手性亚基的-二醇部分；冠醚（S，S，S，S）-1在与2-取代的2-氨基乙醇衍生物络合中显示出高手性识别行为。
• Preparation and temperature-dependent enantioselectivities of homochiral phenolic crown ethers having aryl chiral barriers: thermodynamic parameters for enantioselective complexation with chiral amines
  作者：Koichiro Naemura、Kazuyuki Nishioka、Kazuko Ogasahara、Yasushi Nishikawa、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/s0957-4166(97)00638-1

  日期：1998.2

  Homochiral crown ether (S,S)-1 containing I-naphthyl groups as chiral barriers together with the phenol moiety was prepared by using (S)-3 as a chiral subunit which was resolved in enantiomerically pure form by lipase-catalyzed enantioselective acylation of (+/-)-3. Homochiral phenolic crown ether (S,S)-2, containing phenyl groups as chiral barriers, was also prepared from (S)-5 which was derived from (S)-mandelic acid. The association constants for their complexes with chiral amines in CHCl(3) were determined at various temperatures by the UV-visible spectroscopic method demonstrating that the crown ethers (S,S)-1 and (S,S)-2 displayed the large Delta(R-S)Delta G values of 6.2 and 6.4 kJ mol(-1), respectively, towards the amine 21 at 15 degrees C. Thermodynamic parameters for complex formation were also determined and a linear correlation between T Delta(R-S)Delta S and Delta(R-S)Delta H values was observed. (C) 1998 Elsevier Science Ltd. All rights reserved.