(3R,6S)-3-bromo-3,6-dimethyl-1,4-dioxane-2,5-dione | 1071822-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (3R,6S)-3-bromo-3,6-dimethyl-1,4-dioxane-2,5-dione
• CAS: 1071822-16-6
• 化学式: C₆H₇BrO₄
• 分子量: 223.023
• InChiKey: RBUFMHWWHJQGNB-DZSWIPIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (3R,6S)-3-bromo-3,6-dimethyl-1,4-dioxane-2,5-dione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(6S)-3-methylene-6-methyl-1,4-dioxane-2,5-dione
  参考文献：
  名称：

  Well-Defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side Chains

  摘要：

  Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available L-lactide. The key step in the synthesis is the 1,3-dipolar cycloacklition between PEG-azides and a highly strained spirolactide heptene monomer, which proceeds in high conversions. The PEG-grafted lactide analogues were polymerized via ring-opening polymerization using triazabicydodecene as organocatalyst to give well-defined tri- and hepta(ethylene glycol)-poly(lactide)s (PLA) with molecular weights above 10 kDa and polydispersity indices between 1.6 and 2.1. PEG poly(lactide) (PLA) with PEG chain M-n 2000 was also prepared, but GPC analysis showed a bimodal profile indicating the presence of starting macromonomer. Cell adhesion assays were performed using MC3T3-E1 osteoblast-like cells demonstrating that PEG-containing PLA reduces cell adhesion significantly when compared to unfunctionalized PLA.

  DOI：

  10.1021/ma2016387
• 作为产物：
  描述：

  L-丙交酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 苯 为溶剂， 以79%的产率得到(3R,6S)-3-bromo-3,6-dimethyl-1,4-dioxane-2,5-dione
  参考文献：
  名称：

  Well-Defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side Chains

  摘要：

  Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available L-lactide. The key step in the synthesis is the 1,3-dipolar cycloacklition between PEG-azides and a highly strained spirolactide heptene monomer, which proceeds in high conversions. The PEG-grafted lactide analogues were polymerized via ring-opening polymerization using triazabicydodecene as organocatalyst to give well-defined tri- and hepta(ethylene glycol)-poly(lactide)s (PLA) with molecular weights above 10 kDa and polydispersity indices between 1.6 and 2.1. PEG poly(lactide) (PLA) with PEG chain M-n 2000 was also prepared, but GPC analysis showed a bimodal profile indicating the presence of starting macromonomer. Cell adhesion assays were performed using MC3T3-E1 osteoblast-like cells demonstrating that PEG-containing PLA reduces cell adhesion significantly when compared to unfunctionalized PLA.

  DOI：

  10.1021/ma2016387

文献信息

• A Bifunctional Monomer Derived from Lactide for Toughening Polylactide
  作者：Feng Jing、Marc A. Hillmyer

  DOI：10.1021/ja804357u

  日期：2008.10.22

  the dienophile to prepare spiro[6-methyl-1,4-dioxane-2,5-dione-3,2'-bicyclo[2.2.1]hept[5]ene] via an exoselective and diastereofacial-selective Diels-Alder reaction. Polymerizations of this bifunctional lactide derivative were successfully carried out under ring-opening and ring-opening metathesis polymerization conditions to yield high molecular weight and high Tg polymers. We further demonstrated

  (6S)-3-Methylene-6-methyl-1,4-dioxane-2,5-dione 由 L-丙交酯合成并用作亲二烯体制备螺[6-methyl-1,4-dioxane-2, 5-dione-3,2'-bicyclo[2.2.1]hept[5]ene] 通过外选择性和非对映面选择性 Diels-Alder 反应。这种双功能丙交酯衍生物在开环和开环复分解聚合条件下成功聚合，得到高分子量和高 Tg 聚合物。我们进一步证明，通过将少量螺[6-甲基-1,4-二恶烷-2,5-二酮-3,2'-双环[2.2.1]庚[5]烯]加入聚（1， 5-环辛二烯）并将其与 DL-丙交酯共聚，可以制造出新型 PLA 聚合物合金，其韧性比 PLA 和相应的 PLA 和聚（1,5-环辛二烯）的二元共混物具有巨大的改进。
• BIFUNCTIONAL LACTIDE MONOMER DERIVATIVE AND POLYMERS AND MATERIALS PREPARED USING THE SAME
  申请人：Jing Feng

  公开号：US20090306333A1

  公开（公告）日：2009-12-10

  The invention described herein provides a novel lactide monomer derivative and process for preparing the lactide monomer derivative. The monomer derivative of the invention is bifunctional in nature, and can be employed a variety of efficient synthesis processes to prepare various polymers. Further, the bifunctional monomer derivative can be used to prepare various intermediate-stage compounds and polymers, which in turn can be used to synthesize other compounds, polymers, copolymers and composites. The lactide monomer derivative has a bifunctional norbornene spiro lactide structure, spiro[6-methyl-1,4-dioxane-2,5-dione-3,2′-bicyclo[2.2.1]hept[5]ene], and structure as follows: and stereoisomers thereof. The lactide monomer derivative is bifunctional in that either 1) the norbornene ring, 2) lactide ring, or 3) both, can be opened and used in polymer synthesis for the backbone or the reactive branch for other polymeric syntheses.

  本发明提供了一种新型的乳酸内酯单体衍生物及其制备方法。该发明的单体衍生物具有双功能性质，可以用于多种高效合成过程以制备各种聚合物。此外，该双功能单体衍生物可用于制备各种中间体化合物和聚合物，进而可用于合成其他化合物、聚合物、共聚物和复合材料。乳酸内酯单体衍生物具有双功能的去氢松环戊烯螺内酯结构，spiro[6-甲基-1,4-二氧杂环己烷-2,5-二酮-3,2'-双环[2.2.1]庚[5]烯]，其结构如下：以及其立体异构体。乳酸内酯单体衍生物具有双功能性质，即1）去氢松环戊烯环，2）乳酸内酯环，或3）两者均可打开并用于聚合物合成的骨架或反应支链。
• US8203007B2
  申请人：——

  公开号：US8203007B2

  公开（公告）日：2012-06-19
• Well-Defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side Chains
  作者：José A. Castillo、Dorothee E. Borchmann、Amy Y. Cheng、Yufeng Wang、Chunhua Hu、Andrés J. García、Marcus Weck

  DOI：10.1021/ma2016387

  日期：2012.1.10

  Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available L-lactide. The key step in the synthesis is the 1,3-dipolar cycloacklition between PEG-azides and a highly strained spirolactide heptene monomer, which proceeds in high conversions. The PEG-grafted lactide analogues were polymerized via ring-opening polymerization using triazabicydodecene as organocatalyst to give well-defined tri- and hepta(ethylene glycol)-poly(lactide)s (PLA) with molecular weights above 10 kDa and polydispersity indices between 1.6 and 2.1. PEG poly(lactide) (PLA) with PEG chain M-n 2000 was also prepared, but GPC analysis showed a bimodal profile indicating the presence of starting macromonomer. Cell adhesion assays were performed using MC3T3-E1 osteoblast-like cells demonstrating that PEG-containing PLA reduces cell adhesion significantly when compared to unfunctionalized PLA.