2-[4-(2-[D4]Iodoethoxy)-3-[D3]methoxybenzyloxy]tetrahydropyran | 347894-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[4-(2-[D4]Iodoethoxy)-3-[D3]methoxybenzyloxy]tetrahydropyran
• 英文别名: 2-[[4-(1,1,2,2-Tetradeuterio-2-iodoethoxy)-3-(trideuteriomethoxy)phenyl]methoxy]oxane
• CAS: 347894-41-1
• 化学式: C₁₅H₂₁IO₄
• 分子量: 399.178
• InChiKey: IUXBOOBSIDCBKN-QXAASDFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(2-[D4]Iodoethoxy)-3-[D3]methoxybenzyloxy]tetrahydropyran 在 甲酸 、 4-甲基苯磺酸吡啶 、 caesium carbonate 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成
  参考文献：
  名称：

  Synthesis of Deuterium-Labeled Cryptophane-A and Investigation of Xe@Cryptophane Complexation Dynamics by 1D-EXSY NMR Experiments

  摘要：

  We present the synthesis of a series of deuterated cryptophanes 2-6 by a slightly modified procedure used for cryptophane-A. We show that for [Xe@cryptophane] complexes the use of variable-temperature one-dimensional 129Xe magnetization transfer (1D-EX-SY) allows the measurement of exchange rates. From these data the decomplexation activation energy Ea has been estimated to be 37.5+/-2 kJ mol(-1). The decomplexation activation enthalpy, deltaH(++) = 35.5+/-2 kJ mol(-1), and entropy, deltaS(++) = -60+/-5 J mol(-1) K(-1), have also been calculated. The calculated negative activation entropy suggests that the activated complex associated with decomplexation is conformationally more strained than the complex in its ground state.

  DOI：

  10.1002/1521-3765(20010401)7:7<1561::aid-chem1561>3.0.co;2-9
• 作为产物：
  描述：

  (4-Allyloxy-3-[D3]methoxyphenyl)methanol 在 palladium diacetate 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 二乙胺 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 2-[4-(2-[D4]Iodoethoxy)-3-[D3]methoxybenzyloxy]tetrahydropyran
  参考文献：
  名称：

  Synthesis of Deuterium-Labeled Cryptophane-A and Investigation of Xe@Cryptophane Complexation Dynamics by 1D-EXSY NMR Experiments

  摘要：

  We present the synthesis of a series of deuterated cryptophanes 2-6 by a slightly modified procedure used for cryptophane-A. We show that for [Xe@cryptophane] complexes the use of variable-temperature one-dimensional 129Xe magnetization transfer (1D-EX-SY) allows the measurement of exchange rates. From these data the decomplexation activation energy Ea has been estimated to be 37.5+/-2 kJ mol(-1). The decomplexation activation enthalpy, deltaH(++) = 35.5+/-2 kJ mol(-1), and entropy, deltaS(++) = -60+/-5 J mol(-1) K(-1), have also been calculated. The calculated negative activation entropy suggests that the activated complex associated with decomplexation is conformationally more strained than the complex in its ground state.

  DOI：

  10.1002/1521-3765(20010401)7:7<1561::aid-chem1561>3.0.co;2-9

文献信息

• Cryptophanols, new versatile compounds for the synthesis of functionalized cryptophanes and polycryptophanesElectronic supplementary information (ESI) available: experimental details for compounds 4, 5, 6, 7, 8 and 14. See http://www.rsc.org/suppdata/cc/b1/b109301k/
  作者：Magali Darzac、Thierry Brotin、Denis Bouchu、Jean-Pierre Dutasta

  DOI：10.1039/b109301k

  日期：2002.1.14

  After deprotection with a palladium catalyst, mono-allylated cryptophane-A (1, 2) and cryptophane-E (3) gave the new cryptophanols 4, 5 and 6, respectively, which are important key compounds for the preparation of mono-functionalized cryptophanes as well as for the design of large supramolecular hosts such as the bis-cryptophanes 7 and 8.

  在钯催化剂的作用下进行脱保护处理后，单烯丙基化的隐烷-A（1、2）和隐烷-E（3）分别得到了新的隐烷醇 4、5 和 6，它们是制备单官能化隐烷以及设计双隐烷 7 和 8 等大型超分子宿主的重要关键化合物。