tetraethylene glycol mono(bicyclo[2.2.1]hept-5-ene-2-carboxylate) | 724785-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetraethylene glycol mono(bicyclo[2.2.1]hept-5-ene-2-carboxylate)
• CAS: 724785-16-4
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: OAPICLBYPHHLLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  22.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tetraethylene glycol mono(bicyclo[2.2.1]hept-5-ene-2-carboxylate) 在 4-二甲氨基吡啶 、 DOWEX 50X₂-400 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 2-[2-[2-[2-[3-Hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxyethoxy]ethoxy]ethoxy]ethyl bicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis of Ultralarge Molecular Weight Bottlebrush Polymers Using Grubbs' Catalysts

  摘要：

  This paper describes two methods to synthesize bottlebrush polymers with molecular weights from 1 million to over 60 million g mol(-1) using Grubbs' first and second generation catalysts. In the first method, macromonomers of poly(L-lactide) were synthesized using tin(II) 2-ethylhexanoate and terminated on one end with a norbornyl group. Grubbs' first generation catalyst polymerized macromonomers with one poly(L-lactide) chain per norbornene, and Grubbs' second generation catalyst polymerized macromonomers with two poly(L-lactide) chains per norbornene. The predicted and measured molecular weights closely matched each other, and the polydispersities of the bottlebrush polymers were between 1.05 and 1.39. These examples are the first where Grubbs' second generation catalyst can be considered living for ROMP. In the second method, the backbone was polymerized first, and polylactide arms with molecular weights from 15 000 to 50 000 g mol(-1) were polymerized from the backbone. Polymers that were shaped as spheres or rigid rods were synthesized. The polymers were analyzed by GPC, MALLS, QELS, and H-1 NMR.

  DOI：

  10.1021/ma049647k
• 作为产物：
  描述：

  三缩四乙二醇 、 5-降冰片烯-2-羧酸 在 草酰氯 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到tetraethylene glycol mono(bicyclo[2.2.1]hept-5-ene-2-carboxylate)
  参考文献：
  名称：

  Synthesis of Ultralarge Molecular Weight Bottlebrush Polymers Using Grubbs' Catalysts

  摘要：

  This paper describes two methods to synthesize bottlebrush polymers with molecular weights from 1 million to over 60 million g mol(-1) using Grubbs' first and second generation catalysts. In the first method, macromonomers of poly(L-lactide) were synthesized using tin(II) 2-ethylhexanoate and terminated on one end with a norbornyl group. Grubbs' first generation catalyst polymerized macromonomers with one poly(L-lactide) chain per norbornene, and Grubbs' second generation catalyst polymerized macromonomers with two poly(L-lactide) chains per norbornene. The predicted and measured molecular weights closely matched each other, and the polydispersities of the bottlebrush polymers were between 1.05 and 1.39. These examples are the first where Grubbs' second generation catalyst can be considered living for ROMP. In the second method, the backbone was polymerized first, and polylactide arms with molecular weights from 15 000 to 50 000 g mol(-1) were polymerized from the backbone. Polymers that were shaped as spheres or rigid rods were synthesized. The polymers were analyzed by GPC, MALLS, QELS, and H-1 NMR.

  DOI：

  10.1021/ma049647k

文献信息

• Influence of Various Silyl Protecting Groups on Stereoselective 2-Deoxyrhamnosylation
  作者：Ananya Mukherji、Mahendra K. V. Rotta、Bikash K. Sarmah、Pavan K. Kancharla

  DOI：10.1021/acs.joc.2c02285

  日期：2023.1.6

  The influence of various silyl protecting groups on 2-deoxyrhamnosylation using 2-deoxyrhamnosyl acetates, thioglycosides, and (p-methoxyphenyl)vinylbenzoate (PMPVB) donors has been presented. C-Glycosylation reactions reveal that tert-butyldimethylsilyl (TBDMS), triisopropylsilyl (TIPS), and tert-butyldiphenylsilyl (TBDPS) silyl protected rhamnosyl oxocarbenium ions have no facial selectivity except

  已经介绍了各种甲硅烷基保护基对使用 2-脱氧鼠李糖醋酸酯、硫糖苷和 ( p-甲氧基苯基) 苯甲酸乙烯酯 (PMPVB) 供体进行 2-脱氧鼠李糖基化的影响。C-糖基化反应表明，叔丁基二甲基甲硅烷基 (TBDMS)、三异丙基甲硅烷基 (TIPS) 和叔丁基二苯基甲硅烷基 (TBDPS) 甲硅烷基保护的鼠李糖基氧碳鎓离子没有面部选择性，除了构象 ( 4 H 3 ) 锁定的四异丙基二硅氧烷 (TIPDS) 保护的鼠李糖供体，它提供完整的 α-选择性。然而，发现 TBDPS 保护的鼠李糖基供体是 α-立体选择性O的优良保护基团-与各种受体的糖基化反应。观察到的结果在供体和供体激活条件下是一致的。最重要的是，这项研究是在室温下进行的，这与其他能源密集型低温研究不同，必然具有更多的实用性。已使用动力学和热力学分析解释了结果。