(4R,9R,17R,22R)-9,17-diphenyl-27,29-dimethoxy-3,10,13,16,23-pentaoxatetracyclo<23.3.1.0^4,9.0^17,22>nonacosa-1(28),25(29),26(27)-triene | 167356-43-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R,9R,17R,22R)-9,17-diphenyl-27,29-dimethoxy-3,10,13,16,23-pentaoxatetracyclo<23.3.1.0^4,9.0^17,22>nonacosa-1(28),25(29),26(27)-triene
• 英文别名: (4R,9R,17R,22R)-(-)-27,29-Dimethoxy-9,17-diphenyl-3,10,13,16,23-pentaoxatetracyclo<23.3.1.0^4,9.0^17,22>nonacosa-1(29)-25,27-triene；(4R,9R,17R,22R)-27,29-dimethoxy-9,17-diphenyl-3,10,13,16,23-pentaoxatetracyclo[23.3.1.04,9.017,22]nonacosa-1(28),25(29),26-triene
• CAS: 167356-43-6
• 化学式: C₃₈H₄₈O₇
• 分子量: 616.795
• InChiKey: JMQVBGHHTDLERF-QEZSNJNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  45
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,9R,17R,22R)-9,17-diphenyl-27,29-dimethoxy-3,10,13,16,23-pentaoxatetracyclo<23.3.1.0^4,9.0^17,22>nonacosa-1(28),25(29),26(27)-triene 在 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (4R,9R,17R,22R)-9,17-diphenyl-3,10,13,16,23-pentaoxatetracyclo[23.3.1.04,9.017,22]nonacosa-1(28),25-diene-27,29-dione
  参考文献：
  名称：

  以顺-1-苯基环己烷-1,2-二醇为手性亚基，2,4-二硝基苯基偶氮苯酚为生色团的偶氮酚冠醚的制备及对映体识别行为

  摘要：

  制备了具有两个顺式-1-苯基环己烷-1,2-二醇手性亚基和对-（2,4-二硝基苯基偶氮）苯酚部分作为生色团的旋光偶氮酚冠醚1和2 ，该对映体可识别成色，与已经研究了手性乙胺和2-氨基乙醇衍生物。基于对映异构体配合物的CPK分子模型检查，可以解释冠醚1和2所观察到的对映异构体选择性。

  DOI：

  10.1039/p19960000383
• 作为产物：
  描述：

  1,3-bis-bromomethyl-2,5-dimethoxy-benzene 、 2,2'-Oxydiethylenedioxybis(2-phenylcyclohexanol) 在 sodium hydride 、 氟硼酸钾 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 20.0h， 以80%的产率得到(4R,9R,17R,22R)-9,17-diphenyl-27,29-dimethoxy-3,10,13,16,23-pentaoxatetracyclo<23.3.1.0^4,9.0^17,22>nonacosa-1(28),25(29),26(27)-triene
  参考文献：
  名称：

  以顺-1-苯基环己烷-1,2-二醇为手性亚基，2,4-二硝基苯基偶氮苯酚为生色团的偶氮酚冠醚的制备及对映体识别行为

  摘要：

  制备了具有两个顺式-1-苯基环己烷-1,2-二醇手性亚基和对-（2,4-二硝基苯基偶氮）苯酚部分作为生色团的旋光偶氮酚冠醚1和2 ，该对映体可识别成色，与已经研究了手性乙胺和2-氨基乙醇衍生物。基于对映异构体配合物的CPK分子模型检查，可以解释冠醚1和2所观察到的对映异构体选择性。

  DOI：

  10.1039/p19960000383

文献信息

• Chiral Recognition in Host-Guest Complexation Determined by the Enantiomer-Labeled Guest Method Using Fast Atom Bombardment Mass Spectrometry
  作者：Masami Sawada、Yoshio Takai、Hitoshi Yamada、Shigeki Hirayama、Takahiro Kaneda、Toshikazu Tanaka、Kimiko Kamada、Takashi Mizooku、Sachiko Takeuchi

  DOI：10.1021/ja00134a017

  日期：1995.7

  Chiral recognition in host-guest complexations between crown ether hosts (H) and amino acid ester ammonium ion guests (G(+)) has been evaluated by fast atom bombardment (FAB) mass spectrometry (m-nitrobenzyl alcohol matrix). The method uses a 1/1 mixed (for example, G(R)(+) and G(s-dn)(+)) solution of the guest whose enantiomer is isotopically (deuterium) labeled. Chiral recognition of a given host is simply measured with a given guest from the peak intensity ratio of the two diastereomeric host-guest complex ions as I[(H + G(R))(+)]/I[(H + G(S-dn))(+)] drop I-R/I-S-dn. Both the degree and the direction of chiral recognition are characterized by the I-R/I-S-dn values in the range from 0.5 to 5.4 (I-R/I-S-d3) for the present host-guest combination systems studied. Among several synthetic chiral crown ethers and related natural host compounds, it has been found that host 5 possesses remarkably large guest dependence upon the chiral recognition properties: (1) toward primary amino acid ester guests 14-21, a high degree of (R)-enantiomer preference (I-R/I-S = 3.2-5.4), (2) toward phenylglycine ester guest 22, almost no enantiomer recognition (I-R/I-S = 1.1), and (3) toward secondary amino acid ester guest 24, a weak (S)-enantiomer preference (I-R/I-S = 0.7). It is also shown that the I-R/I-S values measured with the present concentrations are reasonably correlated with the relative thermodynamic stabilities in the corresponding host-guest equilibria in solution (I-R/I-S less than or equal to K-R/K-S) for three typical host-guest combination systems selected (1-22, 4-16, and 5-16). Accordingly, the present FABMS/EL (enantiomer-labeled guest) method can be proposed as a new and practically useful technique for determining chiral recognition properties in the highly structured chiral host-chiral guest complexations.