4-Methyl-25,26,27,28-tetrapropoxy-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene | 1204604-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Methyl-25,26,27,28-tetrapropoxy-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
• CAS: 1204604-56-7
• 化学式: C₃₇H₄₂O₄S₄
• 分子量: 679.002
• InChiKey: JLKWQTFIRIBPOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  25,26,27,28-Tetrapropoxy-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-4-carbaldehyde 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到4-Methyl-25,26,27,28-tetrapropoxy-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
  参考文献：
  名称：

  Uncommon Regioselectivity in the Thiacalix[4]arene Series: Gross Formylation of the Cone Conformer

  摘要：

  Thiacalix[4]arene immobilized in the cone conformation undergoes a direct Gross formylation reaction (Cl2CH-O-CH3/SnCl4/CH2Cl2) to give the upper-rim formylated thiacalixarene. Albeit using excess of the formylation agent and various reaction temperatures, only one formyl group is introduced into the meta position of the thiacalixarene skeleton. The surprising regioselectivity indicates dramatically different reactivity of the thiacalix[4]arene system when compared with a classical calix[4]arene analogue, which yields exclusively para isomers. The introduction of functional groups into the meta position represents an exceptional substitution pattern in thiacalixarene chemistry, which imparts in interesting conformational behavior to these compounds. The systematic NMR study revealed that the pinched cone-pinched cone equilibrium is remarkably shifted toward one pinched cone structure depending on the substitution.

  DOI：

  10.1021/jo902240h

文献信息

• Uncommon Regioselectivity in the Thiacalix[4]arene Series: Gross Formylation of the <i>Cone</i> Conformer
  作者：Ondrej Kundrat、Hana Dvorakova、Vaclav Eigner、Pavel Lhotak

  DOI：10.1021/jo902240h

  日期：2010.1.15

  Thiacalix[4]arene immobilized in the cone conformation undergoes a direct Gross formylation reaction (Cl2CH-O-CH3/SnCl4/CH2Cl2) to give the upper-rim formylated thiacalixarene. Albeit using excess of the formylation agent and various reaction temperatures, only one formyl group is introduced into the meta position of the thiacalixarene skeleton. The surprising regioselectivity indicates dramatically different reactivity of the thiacalix[4]arene system when compared with a classical calix[4]arene analogue, which yields exclusively para isomers. The introduction of functional groups into the meta position represents an exceptional substitution pattern in thiacalixarene chemistry, which imparts in interesting conformational behavior to these compounds. The systematic NMR study revealed that the pinched cone-pinched cone equilibrium is remarkably shifted toward one pinched cone structure depending on the substitution.