2-<2-<2-(tosyloxy)ethoxy>phenyl>-1,3-dioxolane | 133967-53-0

• 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-<2-<2-(tosyloxy)ethoxy>phenyl>-1,3-dioxolane
• 英文别名: 2-(2'-(tosyloxy)ethoxy)benzaldehyde ethylene acetal；2-[2-(1,3-dioxolan-2-yl)phenoxy]ethyl 4-methylbenzenesulfonate
• CAS: 133967-53-0
• 化学式: C₁₈H₂₀O₆S
• 分子量: 364.419
• InChiKey: QXZVQNQCTOEVSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-<2-<2-(tosyloxy)ethoxy>phenyl>-1,3-dioxolane 在 氢氧化钾 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 1.02h， 生成 1,2,4,5-tetrakis(2'-(o-formylphenoxy)ethoxy)benzene
  参考文献：
  名称：

  Four-Atom-Linked Capped Porphyrins:  Synthesis and Characterization

  摘要：

  Three new capped porphyrins, H-2(OC(2)OPor) (7), H-2(OC(CO)NPor) (13), and H-2(OC(2)NPor) (14), to be used as heme model compounds, have been synthesized and characterized. These compounds have the shortest linkages between cap and porphyrin plane of any four-arm capped porphyrins synthesized to date. The general synthetic procedure for H-2(OC(2)OPor) involves the reaction of a tetraaldehyde ''cap'' with pyrrole to form the capped porphyrin. In the synthesis of the tetraamide-capped porphyrin, H-2(OC(CO)NPor), a tetraacid chloride cap is reacted with meso-alpha,alpha,alpha,alpha-tetra-(o-aminophenyl)porphyrin. The amide groups may be reduced to form H-2(OC(2)NPor). With the use of FeBr2, Fe2+ may be inserted in high yield into Ha(2)(OC(2)OPor) and H-2(OC(CO)NPor). The crystal structures of H-2(OC(2)NPor), Fe(OC(2)OPor)(OMe), and [Fe(OC(2)OPor)](2)(mu-O) provide details on the types and amounts of cap expansion necessary to accommodate small ligands of biological interest, such as O-2 and CO.

  DOI：

  10.1021/jo9521615
• 作为产物：
  描述：

  乙二醇 、 2-<2-(tosyloxy)ethoxy>benzaldehyde 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以89%的产率得到2-<2-<2-(tosyloxy)ethoxy>phenyl>-1,3-dioxolane
  参考文献：
  名称：

  Four-Atom-Linked Capped Porphyrins:  Synthesis and Characterization

  摘要：

  Three new capped porphyrins, H-2(OC(2)OPor) (7), H-2(OC(CO)NPor) (13), and H-2(OC(2)NPor) (14), to be used as heme model compounds, have been synthesized and characterized. These compounds have the shortest linkages between cap and porphyrin plane of any four-arm capped porphyrins synthesized to date. The general synthetic procedure for H-2(OC(2)OPor) involves the reaction of a tetraaldehyde ''cap'' with pyrrole to form the capped porphyrin. In the synthesis of the tetraamide-capped porphyrin, H-2(OC(CO)NPor), a tetraacid chloride cap is reacted with meso-alpha,alpha,alpha,alpha-tetra-(o-aminophenyl)porphyrin. The amide groups may be reduced to form H-2(OC(2)NPor). With the use of FeBr2, Fe2+ may be inserted in high yield into Ha(2)(OC(2)OPor) and H-2(OC(CO)NPor). The crystal structures of H-2(OC(2)NPor), Fe(OC(2)OPor)(OMe), and [Fe(OC(2)OPor)](2)(mu-O) provide details on the types and amounts of cap expansion necessary to accommodate small ligands of biological interest, such as O-2 and CO.

  DOI：

  10.1021/jo9521615

文献信息

• Hexaphyrin-cyclodextrin hybrids: Getting larger, getting confused
  作者：François Robert、Bernard Boitrel、Mickaël Ménand、Stéphane Le Gac

  DOI：10.1142/s1088424621500929

  日期：2021.10

  acidic conditions, followed by DDQ oxidation. Doubly-linked HCD hybrids were obtained with structural variations in the hexaphyrin macrocycles depending on the MSA concentration (2 vs. 200 mM) producing either regular ([26] rectangular/[28] Möbius) or doubly N-confused dioxo ([26] rectangular) scaffolds. For the latter, two isomers were isolated featuring mirror transoid skeletons and long-side meso-linking

  六氢卟啉-环糊精杂化物 (HCD) 的多样性，以前由常规六氢卟啉和α-环糊精亚基已按照两个主要方向增加：扩大环糊精提供的有限空间和针对双金属配合物调整六氢卟啉的 N 核。较大的β-环糊精单元在其初级边缘上被醛接头选择性地官能化，进一步与 2 eq 反应。在酸性条件下对五氟苯基三吡喃进行氧化，然后进行 DDQ 氧化。根据 MSA 浓度（2对比. 200 mM）产生常规（[26] 矩形/[28] 莫比乌斯）或双重 N-混淆二氧（[26] 矩形）支架。对于后者，分离出两种异构体，具有镜面转体骨架和长边中观-连接模式，在强烈和相反的电子圆二色性（ECD）光谱的起源处产生平面手性。然后研究了 Zn(II) 络合导致两个主要发现。(i) 常规的 [28] Möbius HCD 在 acac 配体存在下提供了单金属 Möbius Zn(II) 配合物的混合物。ECD光谱表明手性转移β-环糊精有利于磷莫比
• Orchestrating Communications in a Three-Type Chirality Totem: Remote Control of the Chiroptical Response of a Möbius Aromatic System
  作者：Rajaa Benchouaia、Nicolas Cissé、Bernard Boitrel、Matthieu Sollogoub、Stéphane Le Gac、Mickaël Ménand

  DOI：10.1021/jacs.9b04074

  日期：2019.7.24

  sustain dynamic chirality transfer. In this context, we report herein the first example of a Möbius aromatic ring capped by a cavity, consisting in a Möbius [28]hexaphyrin doubly-linked to an α-cyclodextrin. This unique design affords a "totem" of three different chirality elements arising from the cyclodextrin (fix central chirality), the bridging pattern (dynamic planar chirality) and the hexaphyrin

  在各种类型的手性（中心、轴向、螺旋、平面……）中，莫比乌斯拓扑固有的手性几乎仍未被探索，部分原因是难以获得莫比乌斯化合物。在过去的十年中，[28] 六卟啉已经成为建立莫比乌斯芳香性的最佳候选物之一。虽然需要控制它们的灵活性以获得 P/M 扭曲对映选择性，但维持动态手性转移可能会引起极大兴趣。在这种情况下，我们在此报告了第一个被空腔封盖的莫比乌斯芳环的例子，由一个与 α-环糊精双重连接的莫比乌斯 [28] 六卟啉组成。这种独特的设计提供了由环糊精（固定中心手性）产生的三种不同手性元素的“图腾”，桥接模式（动态平面手性）和六卟啉（动态拓扑手性）。手性转移（见 TOC 图）的特点是立体特异性平面到拓扑通讯（直径过量 > 95 %；迄今为止报道的莫比乌斯环的最高不对称选择性）与立体选择性中心到平面通讯（向上）相结合至 60% 径向过量）。有趣的是，立体选择性是通过与六卟啉的非手性效应物的协调来远程控制的，将莫比乌斯芳族
• Johnson, Martin R.; Seok, Won K.; Ibers, James A., Journal of the American Chemical Society, 1991, vol. 113, # 10, p. 3998 - 4000
  作者：Johnson, Martin R.、Seok, Won K.、Ibers, James A.

  DOI：——

  日期：——
• JOHNSON, MARTIN R.;SEOK, WON K.;IBERS, JAMES A., J. AMER. CHEM. SOC., 113,(1991) N0, C. 3998-4000
  作者：JOHNSON, MARTIN R.、SEOK, WON K.、IBERS, JAMES A.

  DOI：——

  日期：——
• Capped-porphyrin precursors
  作者：P. G. Jene、D. S. Chan、B. L. Cooke、J. A. Ibers

  DOI：10.1107/s0108270198018034

  日期：1999.5.15

  In the crystalline state, 2-[3-(tosyloxy)propoxy]benzaldehyde [(I), C17H18O5S] exists in a U-shaped conformation. The benzaldehyde and toluene rings are nearly parallel. Crystals of 2-[2(tosyloxy)ethoxy]benzaldehyde occur with two habits. The X-ray structure determinations of these habits reveal an anhydrous form [(II), C16H16O5S] and a hemihydrated form [(III), C16H16O5S.0.5H(2)O] In (III), a water molecule bridges two carbonyl functions [O6...O1 2.87 (1) Angstrom] 1,2,4,5-Tetrakis2-[2-(1,3-dioxolan-2-yl)phenoxy]ethoxy}benzene [(IV), C50H54O16] was prepared by protecting the aldehyde function of (II) or (III) with ethylene glycol and reacting the resulting compound, with 1,2,4,5-tetrahydroxybenzene. Compound (IV) has (1) over bar symmetry.