(1,2,3,4,5-Pentamethylcyclopenta-2,4-dien-1-yl)methyl 2-chloropropanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1,2,3,4,5-Pentamethylcyclopenta-2,4-dien-1-yl)methyl 2-chloropropanoate
• 英文别名: (1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)methyl 2-chloropropanoate
• 化学式: C₁₄H₂₁ClO₂
• 分子量: 256.773
• InChiKey: QODLFHVVMLKWIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  1,2,3,4,5-五甲基环戊二烯 在 正丁基锂 、 四丁基碘化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.75h， 生成 (1,2,3,4,5-Pentamethylcyclopenta-2,4-dien-1-yl)methyl 2-chloropropanoate
  参考文献：
  名称：

  1,2-oxazine linker as a thermal trigger for self-immolative polymers

  摘要：

  We have demonstrated the site-specific thermal activation of self-immolative polymers (SIPs) using a bicyclic oxazine as a temperature-sensitive triggering moiety. The oxazine-based trigger was installed at the junction of a SIP-poly(N,N-dimethylacrylamide) (PDMA) diblock copolymer via oxidation of hydroxyurea end groups on the SIP and in situ [4 + 2] cycloaddition with cyclopentadiene-functionalized PDMA. The trigger undergoes a thermally-driven cycloreversion which ultimately leads to initiation of the depolymerization process. The temperature dependence of activation and depolymerization were investigated, along with the mechanism of activation. The relative rates of depolymerization at different temperatures suggested to us that the thermal trigger design may be a good candidate for on-demand activation of SIPs with minimal background triggering. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.09.048

文献信息

• THERMALLY-ACTIVATED SELF-IMMOLATIVE MATERIALS
  申请人：UNIVERSITY OF WASHINGTON THROUGH ITS CENTER FOR COMMERCIALIZATION

  公开号：US20150368403A1

  公开（公告）日：2015-12-24

  A polymer including a self-immolative polymer segment and a thermally-activated trigger moiety is described. The self-immolative polymer segment includes a head end, a tail end, and a plurality of repeating units. The trigger moiety includes a cycloaddition adduct that is covalently coupled to the head end of the self-immolative polymer segment. When the polymer is exposed to an activation temperature, the cycloaddition adduct undergoes retro-cycloaddition to release the self-immolative polymer segment. The self-immolative polymer segment then decomposes to sequentially release repeating units in a head-to-tail direction.
• US9580553B2
  申请人：——

  公开号：US9580553B2

  公开（公告）日：2017-02-28
• [EN] THERMALLY-ACTIVATED SELF-IMMOLATIVE MATERIALS<br/>[FR] MATÉRIAUX AUTO-IMMOLATEURS THERMO-ACTIVÉS
  申请人：UNIV WASHINGTON CT COMMERCIALI

  公开号：WO2014133620A2

  公开（公告）日：2014-09-04

  A polymer including a self-immolative polymer segment and a thermally-activated trigger moiety is described. The self-immolative polymer segment includes a head end, a tail end, and a plurality of repeating units. The trigger moiety includes a cycloaddition adduct that is covalently coupled to the head end of the self-immolative polymer segment. When the polymer is exposed to an activation temperature, the cycloaddition adduct undergoes retro-cycloaddition to release the self-immolative polymer segment. The self-immolative polymer segment then decomposes to sequentially release repeating units in a head-to-tail direction.
• 1,2-oxazine linker as a thermal trigger for self-immolative polymers
  作者：Gregory I. Peterson、Derek C. Church、Neal A. Yakelis、Andrew J. Boydston

  DOI：10.1016/j.polymer.2014.09.048

  日期：2014.11

  We have demonstrated the site-specific thermal activation of self-immolative polymers (SIPs) using a bicyclic oxazine as a temperature-sensitive triggering moiety. The oxazine-based trigger was installed at the junction of a SIP-poly(N,N-dimethylacrylamide) (PDMA) diblock copolymer via oxidation of hydroxyurea end groups on the SIP and in situ [4 + 2] cycloaddition with cyclopentadiene-functionalized PDMA. The trigger undergoes a thermally-driven cycloreversion which ultimately leads to initiation of the depolymerization process. The temperature dependence of activation and depolymerization were investigated, along with the mechanism of activation. The relative rates of depolymerization at different temperatures suggested to us that the thermal trigger design may be a good candidate for on-demand activation of SIPs with minimal background triggering. (C) 2014 Elsevier Ltd. All rights reserved.