2,4,6-triiodophenyl methacrylate | 101364-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,4,6-triiodophenyl methacrylate
• 英文别名: 2,4,6-triiodophenyl-methacrylate；2,4,6-Triiodophenyl 2-methylprop-2-enoate；(2,4,6-triiodophenyl) 2-methylprop-2-enoate
• CAS: 101364-80-1
• 化学式: C₁₀H₇I₃O₂
• 分子量: 539.878
• InChiKey: XMWLJZBVLQGRDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  471.0±45.0 °C(Predicted)
• 密度：
  2.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,4,6-三碘苯酚 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 以81%的产率得到2,4,6-triiodophenyl methacrylate
  参考文献：
  名称：

  Radio-opaque Micelles for X-ray Imaging

  摘要：

  以碘化单体为基础制备了嵌段共聚物，目的是制造出适用于 X 射线成像的造影剂纳米粒子。采用可逆加成-断裂链转移聚合法合成了以甲基丙烯酸寡（乙二醇）甲基醚（OEGMEMA）和 2-[2′,3′,5′-三碘苯甲酰基]甲基丙烯酸氧乙酯（METB）为基础的嵌段共聚物。由于 METB 单体的溶解度较低，浓度不够高，聚合速度较慢。不过，嵌段共聚过程得到了很好的控制，产生了几种嵌段共聚物 POEGMEMA-b-PMETB，并对其在水中的自组装进行了进一步研究。使用 POEGMEMA55-b-PMETB18、POEGMEMA55-b-PMETB32、POEGMEMA100-b-PMETB22 和 POEGMEMA100-b-PMETB32 制备了胶束。透射电子显微镜和动态光散射显示，胶束的大小在 30 纳米到 45 纳米之间，具体取决于嵌段的大小。在 X 射线分析过程中，发现胶束显示出与 BaSO4 和 Visipaque（碘酒醇）相似的强烈对比。这些胶束现在可进一步用作药物载体，或与生物活性基团共轭以实现靶向作用。

  DOI：

  10.1071/ch13391

文献信息

• Radio-opaque Micelles for X-ray Imaging
  作者：Zhiyong Wang、Teddy Chang、Luke Hunter、Andrew M. Gregory、Marcel Tanudji、Steven Jones、Martina H. Stenzel

  DOI：10.1071/ch13391

  日期：——

  Block copolymers based on iodinated monomers were prepared with the aim of creating nanoparticles as contrast agents suitable for X-ray imaging. Reversible addition–fragmentation chain-transfer polymerization was employed to synthesize block copolymers based on oligo(ethylene glycol) methylether methacrylate (OEGMEMA) and 2-[2′,3′,5′-triiodobenzoyl]oxyethyl methacrylate (METB). The polymerization of METB was found to be slow owing to the low solubility of the monomer, which does not allow high enough concentration to achieve a fast rate of polymerization. However, the block copolymerization was well controlled, resulting in several block copolymers, POEGMEMA-b-PMETB, which were further investigated in regards to their self-assembly in water. Micelles were prepared using POEGMEMA55-b-PMETB18, POEGMEMA55-b-PMETB32, POEGMEMA100-b-PMETB22, and POEGMEMA100-b-PMETB32. Transmission electron microscopy and dynamic light scattering revealed micelle sizes between 30 and 45 nm depending on the block size. The micelles were found to show a strong contrast similar to BaSO4 and Visipaque (iodixanol) during X-ray analysis. These micelles can now further be employed as drug carriers or can be conjugated to a bioactive group for targeting.

  以碘化单体为基础制备了嵌段共聚物，目的是制造出适用于 X 射线成像的造影剂纳米粒子。采用可逆加成-断裂链转移聚合法合成了以甲基丙烯酸寡（乙二醇）甲基醚（OEGMEMA）和 2-[2′,3′,5′-三碘苯甲酰基]甲基丙烯酸氧乙酯（METB）为基础的嵌段共聚物。由于 METB 单体的溶解度较低，浓度不够高，聚合速度较慢。不过，嵌段共聚过程得到了很好的控制，产生了几种嵌段共聚物 POEGMEMA-b-PMETB，并对其在水中的自组装进行了进一步研究。使用 POEGMEMA55-b-PMETB18、POEGMEMA55-b-PMETB32、POEGMEMA100-b-PMETB22 和 POEGMEMA100-b-PMETB32 制备了胶束。透射电子显微镜和动态光散射显示，胶束的大小在 30 纳米到 45 纳米之间，具体取决于嵌段的大小。在 X 射线分析过程中，发现胶束显示出与 BaSO4 和 Visipaque（碘酒醇）相似的强烈对比。这些胶束现在可进一步用作药物载体，或与生物活性基团共轭以实现靶向作用。
• Halogen-containing lens material
  申请人：KUREHA KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0162550A2

  公开（公告）日：1985-11-27

  A lens material having a refractive index n20D of at least 1.57 and an Abbe's number v of at least 30, comprising: a copolymer comprising (I) 10 to 85% by weight of a halogen-containing monomer represented by the following formula (1), (II) 15to 90% by weight of a halogen-containing monomer represented by the following formula (2), and (III) 0 to 20% by weight of a monomer copolymerizable with the above mentioned monomers, the composition of the copolymer being based on the total quantity of the monomers (I), (II), and (III): wherein: D represents in which n represents an integer selected from the group consisting of 0, 1 and 2; each R' represents hydrogen or a methyl group; Y represents CHOH; and r represents 0 or 1; each of X' and X2 represents, independently from each other, a methyl group in which one through three of the hydrogen atoms are substituted by a member selected from the group consisting of bromine, iodine and a hydroxyl group (OH group), with the proviso that the number of substitution of the OH group is only one; X3 represents a methyl group in which one through three of the hydrogen atoms are substituted by a member selected from the group consisting of bromine, iodine and D, with the proviso that the number of substitution of D is only one; wherein at least one of X', X2, and X3 contains at least one bromine or iodine; wherein: each R2 represents hydrogen or a methyl group: p represents an integer selected from the group consisting of 0. 1. 2. and 3; X4 represents bromine or iodine; and q represents an integer selected from the group consisting of 1, 2.3.4. and 5. An example of the copolymer is 1-methacryloxy-2,2-di (bromomethyl)-3-bromopropane. methacryloxypolyethyoxy-2.4.6- tribromobenzene styrene divinylbenzene having a n20D of 1.596 and a v of 35.3.

  一种透镜材料，其折射率 n20D 至少为 1.57 和阿贝数 v 至少为 30 的镜片材料，包括：共聚物，其中(I) 10 至 85% （按重量计）由下式(1)代表的含卤素单体，(II) 15 至 90% （按重量计）由下式(2)代表的含卤素单体，和(III) 0 至 20% （按重量计）可与上述单体共聚的单体，共聚物的组成基于单体(I)、(II)和(III)的总量： 其中D 代表 其中 n 代表选自 0、1 和 2 所组成的组的整数；每个 R'代表氢或甲基；Y 代表 CHOH；r 代表 0 或 1；X'和 X2 各自独立地代表一个甲基，其中一至三个氢原子被选自溴、碘和羟基（OH 基）所组成的组的成员取代，但羟基的取代数仅为一个；X3 代表甲基，其中一至三个氢原子被选自溴、碘和 D 组成的组的成员取代，但 D 的取代数仅为一个；其中 X'、X2 和 X3 中至少有一个含有至少一个溴或碘； 其中：每个 R2 代表氢或甲基：p 代表选自 0、1、2 和 3 的整数；X4 代表溴或碘；以及 q 代表选自 1、2.3.4 和 5 的整数。 共聚物的一个例子是 1-甲基丙烯酰氧基-2,2-二（溴甲基）-3-溴丙烷。 甲基丙烯酰氧基聚乙氧基-2.4.6-三溴苯苯乙烯二乙烯基苯，其 n20D 为 1.596，v 为 35.3。
• Photo-curable acrylate and vinyl resin mixtures having very high refractive indices and low melting points
  申请人：SeeReal Technologies S.A.

  公开号：EP1900760A1

  公开（公告）日：2008-03-19

  Acrylate and vinyl resin mixtures with the properties of photo-curability, very high refractive indices, and low melting points are comprised of (a) one or several multi-halogenated aromatic acrylates or multi-halogenated aromatic methacrylates, typically 2,3,4,5,6-pentabromophenyl acrylate, 2,3,4,5,6-pentabromobenzyl acrylate, 2,3,4,5,6-pentabromophenyl methacrylate, 2,3,4,5,6-pentabromobenzyl methacrylate, 2,4,6-tribromophenyl acrylate, or 2,4,6-tribromophenyl methacrylate, 2,4,6-triiodophenyl acrylate, or 2,4,6-triiodophenyl methacrylate, with a weight percent of 30 to 70 % for each acrylate or methacrylate, preferably 40 to 60 % in the formulation. (b) one or several compounds of condensed aromatics, typically 9-anthracylmethacrylate, with a weight percent of 30 to 70% for each, preferably 40 to 60 % in the formulation. (c) one or several aromatic vinyl compounds, typically 1- or 2-vinyl naphthalene, or N-vinyl carbazole, with a weight percent of 30 to 70 % for each, preferably 40 to 60% in the formulation. (d) and a photo-initiator, e.g. Lucirin TPO-L or lrgacurl84, with a weight percent of 0.1 to 5 %, preferably 0.5 to 1.5 % in the formulation.

  具有光固化、极高折射率和低熔点特性的丙烯酸酯和乙烯基树脂混合物包括 (a) 一种或几种多卤代芳香族丙烯酸酯或多卤代芳香族甲基丙烯酸酯，通常是 2,3,4,5,6- 五溴苯丙烯酸酯、2,3,4,5,6-五溴苄基丙烯酸酯、2,3,4,5,6-五溴苯基甲基丙烯酸酯、2,3,4,5,6-五溴苄基甲基丙烯酸酯、2,4,6-三溴苯丙烯酸酯，或 2,4,6-三溴苯甲基丙烯酸酯，2,4,6-三碘苯基丙烯酸酯，或 2,4,6-三碘苯基甲基丙烯酸酯，每种丙烯酸酯或甲基丙烯酸酯在配方中的重量百分比为 30%至 70%，最好为 40%至 60%。 (b) 一种或几种缩合芳香族化合物，通常是 9-甲基丙烯酸蒽酯，每种化合物的重量百分 比为 30-70%，最好为配方中的 40-60%。 (c) 一种或几种芳香族乙烯基化合物，通常是 1-或 2-乙烯基萘，或 N-乙烯基咔唑，在配方中各占 30-70%，最好是 40-60%。 (d) 一种光引发剂，如 Lucirin TPO-L 或 lrgacurl84，在配方中的重量百分比为 0.1%至 5%，最好为 0.5%至 1.5%。
• CORE AND CORE-SHELL NANOPARTICLES CONTAINING IODINE FOR X-RAY IMAGING
  申请人：Margel Shlomo

  公开号：US20090311192A1

  公开（公告）日：2009-12-17

  Nanoparticles having an average particle size of less than 2000 nm, wherein said nanoparticles comprise a polymer having pendant cleavable iodine substituted groups are provided. Processes for preparing the nanoparticles and their use as a contrast agent for X-ray imaging are also described.
• US4578445A
  申请人：——

  公开号：US4578445A

  公开（公告）日：1986-03-25