2-[4-(2-iodoethoxy)-3-methoxybenzyloxy]-tetrahydropyran | 347894-43-3

• 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-iodoethoxy)-3-methoxybenzyloxy]-tetrahydropyran
• 英文别名: 2-[4-(2-Iodoethoxy)-3-methoxybenzyloxy]tetrahydropyran；2-[[4-(2-Iodoethoxy)-3-methoxyphenyl]methoxy]oxane
• CAS: 347894-43-3
• 化学式: C₁₅H₂₁IO₄
• 分子量: 392.234
• InChiKey: IUXBOOBSIDCBKN-UHFFFAOYSA-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-iodoethoxy)-3-methoxybenzyloxy]-tetrahydropyran 在 甲酸 、 caesium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 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-羟基-3-甲氧基苄醇 在 4-甲基苯磺酸吡啶 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 2-[4-(2-iodoethoxy)-3-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

• Synthesis of Highly Substituted Cryptophane Derivatives
  作者：Thierry Brotin、Dominique Cavagnat、Erwann Jeanneau、Thierry Buffeteau

  DOI：10.1021/jo4007738

  日期：2013.6.21

  synthesis of new cryptophane derivatives 1–4 bearing nine (1, 2) and twelve (3, 4) methoxy substituents. These compounds represent the first examples of cryptophane derivatives bearing more than six substituents attached on the benzene rings. The preparation of these highly substituted cryptophanes was achieved due to the synthesis of a new cyclotrisyringyl derivative obtained from the reaction of

  我们报告新cryptophane衍生物的合成1 - 4轴承9（1，2）和12（3，4）甲氧基取代基。这些化合物代表在苯环上带有六个以上取代基的隐色烯衍生物的第一个例子。由于在催化量的三氟甲磺酸ScSc（OTf）3存在下从受保护的丁香醇反应得到的新的环三丁烯基衍生物的合成，实现了这些高度取代的隐烯基的制备。该反应还以低收率（7％）提供了受保护的环四环丁烯基衍生物，其特征在于11 H NMR，IR和X射线晶体学。与此相反，为cryptophane-A同类物所观察到的，这些高度取代cryptophanes的合成产生了两个抗-和顺式-diastereomers。这些化合物已得到充分表征，并已获得其X射线结构以确定这些新的隐烷衍生物的立体化学。
• A Hybrid Cavitand Made by Capping Permethylated α-Cyclodextrin with Cyclotriveratrylene
  作者：Frédérique Brégier、Sekar Karuppannan、Jean-Claude Chambron

  DOI：10.1002/ejoc.201101604

  日期：2012.4

  A hybrid C 3 -symmetric cavitand 1, in which permethylated α-cyclodextrin (PM α-CDX) is capped with cyclotriveratrylene (CTV), has been prepared in 8 % yield by intramolecular cyclization of a vanillyl alcohol derivative attached to the primary rim of the CDX platform. The reaction proceeds diastereoselectively (dr ≈ 6:1), the chirality of the α-glucopyranosyl units controlling the chirality of the

  杂化 C 3 对称腔体 1，其中全甲基化 α-环糊精 (PM α-CDX) 被环三戊四烯 (CTV) 封端，已通过分子内环化连接到其初级边缘的香草醇衍生物以 8% 的产率制备。 CDX 平台。该反应以非对映选择性（dr ≈ 6:1）进行，α-吡喃葡萄糖基单元的手性控制着 CTV 组分的手性。有趣的是，在极性溶剂中，1 显示出自络合特性，因为 CDX 组分的主要甲氧基直接指向 CTV 腔。
• Xe@cryptophane Complexes with C2 Symmetry: Synthesis and Investigations by 129Xe NMR of the Consequences of the Size of the Host Cavity for Xenon Encapsulation
  作者：Thierry Brotin、Jean-Pierre Dutasta

  DOI：10.1002/ejoc.200390153

  日期：2003.3

  at 278 K) than that observed with cryptophane-A (K = 3900 M−1). The free and bound guests were observed at room temperature under slow-exchange conditions on the 129Xe NMR timescale. A linear relationship was observed between the binding constants and the internal volume of the hosts. Under the same conditions, the Xe@cryptophane-224 [Xe3] complex underwent a fast-exchange process on the NMR timescale

  新的cryptophanes-223 (1)、-233 (2) 和-224 (3) 具有C2 对称性，带有连接两个环三戊四烯单元的不同接头，是按照多步程序合成的。通过 129Xe NMR 光谱研究了氙@cryptophane 配合物的形成。Cryptophanes-223 (1) 和 -233 (2) 在 1,1,2,2-[D2] 四氯乙烷溶液中有效地复合氙气，结合常数稍低（K 在 278 K 时分别为 2810 M-1 和 810 M-1） ) 比用cryptophane-A (K = 3900 M-1) 观察到的。在 129Xe NMR 时间尺度上的缓慢交换条件下，在室温下观察游离和结合客体。在结合常数和宿主的内部体积之间观察到线性关系。在同等条件下，Xe@cryptophane-224 [Xe3] 复合物在 NMR 时间尺度上经历了快速交换过程。解络合活化能 Ea 以及相关参数 ΔH‡
• 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。