divinyl tridecanedioate | 15423-11-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: divinyl tridecanedioate
• 英文别名: Bis(ethenyl) tridecanedioate
• CAS: 15423-11-7
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: FJUDYKIBQYGRNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  divinyl tridecanedioate 、 曲克芦丁 在 吡啶 、 alkaline protease from Bacillus subtilis 作用下， 反应 120.0h， 生成
  参考文献：
  名称：

  Regioselective enzymatic acylation of troxerutin in nonaqueous medium

  摘要：

  A series of monosubstituted troxerutin esters have been synthesized by enzyme-catalyzed regioselective acylation of troxerutin in nonaqueous medium. Using divinyl dicarboxylates (CH2 CH-OOC-(CH2)(n)-COO-CH CH2, n = 2, 3, 4, 7, 8, 11) featuring different chain length as acyl donors and alkaline protease from Bacillus subtilis as catalyst, troxerutin was regioselective acylated at B' ethoxyl group. The results indicated that the regioselectivity of the enzyme-catalyzed acylation was not affected by the chain length of the acyl donor. (C) 2009 Yong Mei Xiao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2009.08.017
• 作为产物：
  描述：

  丙酸乙烯酯 、 十三烷二酸 在 硫酸 、 mercury(II) diacetate 作用下， 反应 4.0h， 以100%的产率得到divinyl tridecanedioate
  参考文献：
  名称：

  Sucrose Derivatives Preparation using Thermomyces lanuginosus Lipase and Their Application

  摘要：

  我们固定了兰氏热霉菌脂肪酶，以催化 DMF 中的酯交换反应。这种脂肪酶是在对其他商用脂肪酶进行筛选后选出的。我们发现，制备的固定化脂肪酶特别适用于制备 6-O-酰基蔗糖，即使在 10 克的规模下也能获得较高的转化率。对几种溶剂进行了选择性酯交换反应评估。我们注意到，固定化脂肪酶在经过 5 个周期 96 小时的反应后，仍能保持 80% 以上的活性。我们还开发了一种通用方法，利用简单的结晶和沉淀过程纯化产物。此外，6-O-乙烯基二甲酰蔗糖通过自由基引发剂合成了相应的聚合物。这种蔗糖支化聚合物可进一步用于评估其生物降解性和其他生物应用。

  DOI：

  10.5012/bkcs.2014.35.2.477

文献信息

• Synthesis of poly (glycerol-co-dioate-co-butanedioate-co-xanthorrhizol) ester and a study of chain length effect on pendant group loading
  作者：Azam sharif mohammed shafioul、Jung In Pyo、Kwan Soo Kim、Chan Seong Cheong

  DOI：10.1016/j.molcatb.2012.05.022

  日期：2012.12

  Natural R-(-)-xanthorrhizol possess a number of therapeutic activities including anti-cancer. The pharmacokinetic properties of that poorly aqueous soluble compound could be improved by incorporating it into polymeric materials. Glycerol can produce a functionalized polymer through a polycondensation process. Enzymatic polycondensation of glycerol and divinylesters was studied and xanthorrhizol was covalently loaded via a butanedioate linker to the polymer backbone. It was observed that xanthorrhizol loading to the polymer backbone increases with the increasing of the chain length of a dioate moiety. Enzyme-mediated xanthorrhizol release from a polymer backbone shows that the polymeric prodrug is able to release xanthorrhizol in a sustained manner. Therefore, the approach described here might be valuable for controlled loading and release of such phenolic sesquiterpenes from the polymeric prodrug. (C) 2012 Elsevier B.V. All rights reserved.
• Sucrose Derivatives Preparation using Thermomyces lanuginosus Lipase and Their Application
  作者：Md. Ashrafuzzaman、Jung In Pyo、Chan Seong Cheong

  DOI：10.5012/bkcs.2014.35.2.477

  日期：2014.2.20

  We immobilized Thermomyces lanuginosus lipase to catalyze transesterification reaction in DMF. This lipase was selected after screening among other commercial lipases. We found that prepared immobilized lipase is particularly useful for preparation of 6-O-acylsucrose with higher conversion rate even in 10 g scale. Several solvents were evaluated for selective transesterification reaction. We noticed that the immobilized lipase retained more than 80 % activity after 5 cycles of 96 h reaction. A general method was also developed to purify the products using simple crystallization and precipitation process. Furthermore, 6-O-vinyladipoylsucrose was subjected to synthesis of the corresponding polymer by radical initiator. The sucrose branched polymer can be used further for evaluation of its biodegradability and other biological applications.

  我们固定了兰氏热霉菌脂肪酶，以催化 DMF 中的酯交换反应。这种脂肪酶是在对其他商用脂肪酶进行筛选后选出的。我们发现，制备的固定化脂肪酶特别适用于制备 6-O-酰基蔗糖，即使在 10 克的规模下也能获得较高的转化率。对几种溶剂进行了选择性酯交换反应评估。我们注意到，固定化脂肪酶在经过 5 个周期 96 小时的反应后，仍能保持 80% 以上的活性。我们还开发了一种通用方法，利用简单的结晶和沉淀过程纯化产物。此外，6-O-乙烯基二甲酰蔗糖通过自由基引发剂合成了相应的聚合物。这种蔗糖支化聚合物可进一步用于评估其生物降解性和其他生物应用。
• Regioselective enzymatic acylation of troxerutin in nonaqueous medium
  作者：Yong Mei Xiao、Pu Mao、Zhen Zhao、Liang Ru Yang、Xian Fu Lin

  DOI：10.1016/j.cclet.2009.08.017

  日期：2010.1

  A series of monosubstituted troxerutin esters have been synthesized by enzyme-catalyzed regioselective acylation of troxerutin in nonaqueous medium. Using divinyl dicarboxylates (CH2 CH-OOC-(CH2)(n)-COO-CH CH2, n = 2, 3, 4, 7, 8, 11) featuring different chain length as acyl donors and alkaline protease from Bacillus subtilis as catalyst, troxerutin was regioselective acylated at B' ethoxyl group. The results indicated that the regioselectivity of the enzyme-catalyzed acylation was not affected by the chain length of the acyl donor. (C) 2009 Yong Mei Xiao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.