[2-[2-[3-[3-[3-[2-[[1,3-Bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxy]-2,2-bis[3-[2-[[1,3-bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxymethyl]propoxy]-3-oxopropyl]sulfanylethoxycarbonylamino]-3-[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropyl] 3-(2-hydroxyethylsulfanyl)propanoate | 1201597-86-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2-[2-[3-[3-[3-[2-[[1,3-Bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxy]-2,2-bis[3-[2-[[1,3-bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxymethyl]propoxy]-3-oxopropyl]sulfanylethoxycarbonylamino]-3-[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropyl] 3-(2-hydroxyethylsulfanyl)propanoate
• 英文别名: [2-[2-[3-[3-[3-[2-[[1,3-bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxy]-2,2-bis[3-[2-[[1,3-bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxymethyl]propoxy]-3-oxopropyl]sulfanylethoxycarbonylamino]-3-[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropyl] 3-(2-hydroxyethylsulfanyl)propanoate
• CAS: 1201597-86-5
• 化学式: C₈₅H₁₄₄N₄O₄₀S₁₂
• 分子量: 2246.87
• InChiKey: LNKDLKZOHYOFCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  141
• 可旋转键数：
  108
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  934
• 氢给体数：
  12
• 氢受体数：
  52

反应信息

• 作为反应物：
  描述：

  1,1-bis(acryloyloxymethyl)ethyl isocyanate 、 [2-[2-[3-[3-[3-[2-[[1,3-Bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxy]-2,2-bis[3-[2-[[1,3-bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxymethyl]propoxy]-3-oxopropyl]sulfanylethoxycarbonylamino]-3-[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropyl] 3-(2-hydroxyethylsulfanyl)propanoate 在 aluminum tris(N-nitroso-N-phenylhydroxylamine) 、 二月桂酸二丁基锡 作用下， 反应 10.0h， 生成
  参考文献：
  名称：

  Alternate Multiaddition Reactions for the Synthesis of Commodity Dendrimers

  摘要：

  本文介绍了通过交替加成法（AMA）实现树枝状聚合物批量生产的单体反应性选择规则。通过使用 2-硫代乙醇和季戊四醇四丙烯酸酯生成四醇，再与 1,1-双（丙烯酰氧基甲基）异氰酸乙酯反应生成树枝状八丙烯酸酯，从而展示了交替加成法的原型。在第二代生长过程中，重复这两种添加方法。

  DOI：

  10.1246/cl.2009.990
• 作为产物：
  描述：

  [3-[3-[2-[[2-Methyl-1,3-di(prop-2-enoyloxy)propan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxy]-2,2-bis[3-[2-[[2-methyl-1,3-di(prop-2-enoyloxy)propan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxymethyl]propyl] 3-[2-[[2-methyl-1,3-di(prop-2-enoyloxy)propan-2-yl]carbamoyloxy]ethylsulfanyl]propanoate 、 2-巯基乙醇 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 [2-[2-[3-[3-[3-[2-[[1,3-Bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxy]-2,2-bis[3-[2-[[1,3-bis[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropan-2-yl]carbamoyloxy]ethylsulfanyl]propanoyloxymethyl]propoxy]-3-oxopropyl]sulfanylethoxycarbonylamino]-3-[3-(2-hydroxyethylsulfanyl)propanoyloxy]-2-methylpropyl] 3-(2-hydroxyethylsulfanyl)propanoate
  参考文献：
  名称：

  Alternate Multiaddition Reactions for the Synthesis of Commodity Dendrimers

  摘要：

  本文介绍了通过交替加成法（AMA）实现树枝状聚合物批量生产的单体反应性选择规则。通过使用 2-硫代乙醇和季戊四醇四丙烯酸酯生成四醇，再与 1,1-双（丙烯酰氧基甲基）异氰酸乙酯反应生成树枝状八丙烯酸酯，从而展示了交替加成法的原型。在第二代生长过程中，重复这两种添加方法。

  DOI：

  10.1246/cl.2009.990

文献信息

• Alternate Multiaddition Reactions for the Synthesis of Commodity Dendrimers
  作者：Ken’ichi Aoki、Kunihiro Ichimura

  DOI：10.1246/cl.2009.990

  日期：2009.10.5

  A selection rule for the reactivity of monomers to realize a quantity production of dendrimers through alternate multiadditions (AMA) is presented. The prototype of the AMA process was shown by using 2-sulfanylethanol and pentaerythritol tetraacrylate to give a tetraol, which was reacted with 1,1-bis(acryloyloxymethyl)ethyl isocyanate as a branched building block to yield a dendritic octaacrylate. Both additions were repeated for the second generation growth.

  本文介绍了通过交替加成法（AMA）实现树枝状聚合物批量生产的单体反应性选择规则。通过使用 2-硫代乙醇和季戊四醇四丙烯酸酯生成四醇，再与 1,1-双（丙烯酰氧基甲基）异氰酸乙酯反应生成树枝状八丙烯酸酯，从而展示了交替加成法的原型。在第二代生长过程中，重复这两种添加方法。
• High-Yield Synthesis of Dendrimers through Alternate Multiaddition Reactions with Commercially Available Reagents
  作者：Ken’ichi Aoki、Kunihiro Ichimura

  DOI：10.1246/bcsj.20110024

  日期：2011.11.15

  An alternate multiaddition (AMA) process consisting of Michael addition and urethane formation is proposed to achieve the quantity synthesis of dendrimers without by-product formation and any weight loss by using commercially available compounds. α-Thioglycerol (TG) was added to pentaerythritol tetraacrylate (PETA) to give the corresponding octaol, but the subsequent reaction with 1,1-bis(acryloyloxymethyl)ethyl isocyanate (BEI) resulted in incomplete urethane formation because of the steric effect of the secondary OH groups. The replacement of BEI with 2-isocyanatoethyl acrylate (AOI) improved the efficiency of the addition of NCO to the secondary OH groups, but an excess amount of AOI was required. Subsequently, we employed the combination of PETA, 2-sulfanylethanol (SE), and BEI. The addition of SE to PETA produced readily the tetraol, which was reacted with BEI to afford dendritic octaacrylate (Ac8b). The repetition of the two addition reactions gave dendritic octaol and hexadecylacrylate (Ac16b), respectively, in large scales. The base-catalyzed Michael addition of 2-naphthalenethiol to acrylate residues of Ac8a and Ac16b gave naphthylthio-terminated dendrimers N8b and N16b, respectively, which were purified by column chromatography. GPC as well as UV-spectroscopic analysis of N8b and N16b revealed that N8b is reasonably monodispersed whereas the purity of N16b is slightly reduced.

  本研究提出了一种由迈克尔加成和脲烷形成组成的交替多重加成（AMA）工艺，利用市场上可买到的化合物实现了树枝状聚合物的定量合成，且无副产物生成和任何重量损失。在季戊四醇四丙烯酸酯（PETA）中加入α-硫代甘油（TG）可得到相应的辛醇，但随后与 1,1-双（丙烯酰氧基甲基）异氰酸乙酯（BEI）反应时，由于仲羟基的立体效应，聚氨酯形成不完全。用 2-异氰酸乙基丙烯酸酯（AOI）代替 BEI，提高了 NCO 与仲羟基加成的效率，但需要过量的 AOI。随后，我们采用了 PETA、2-sulfanylethanol（SE）和 BEI 的组合。在 PETA 中加入 SE 很容易生成四醇，四醇与 BEI 反应生成树枝状八丙烯酸酯（Ac8b）。重复这两个加成反应，可分别得到大规模的树枝状辛醇和十六烷基丙烯酸酯（Ac16b）。在碱催化下，2-萘硫醇与 Ac8a 和 Ac16b 的丙烯酸酯残基发生迈克尔加成反应，分别得到萘硫基封端树枝状聚合物 N8b 和 N16b，并通过柱层析法纯化。对 N8b 和 N16b 进行的 GPC 和紫外光谱分析显示，N8b 的单分散性较好，而 N16b 的纯度则略有降低。