(3R,6R)-3,6-二甲基-1,4-二恶烷-2,5-二酮 | 13076-17-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 中文名称: (3R,6R)-3,6-二甲基-1,4-二恶烷-2,5-二酮
• 中文别名: D(+)-丙交酯
• 英文名称: D-lactide
• 英文别名: L-lactide；(R,R)-lactide；R-lactide；D-LA；(3R,6R)-(+)-3,6-dimethyl-1,4-dioxane-2,5-dione；(3R,6R)-3,6-dimethyl-1,4-dioxane-2,5-dione
• CAS: 13076-17-0
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: JJTUDXZGHPGLLC-QWWZWVQMSA-N

物化性质

• 熔点：
  96.5-97.5 °C
• 沸点：
  285.5±15.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲苯（少许）
• LogP：
  0.4 at 25℃
• 表面张力：
  70.7mN/m at 1g/L and 20℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 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

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2～8℃

制备方法与用途

D-(+)-丙交酯是一种乳酸的环状二酯，它是身体在低氧水平下分解碳水化合物获取能量时肌肉细胞和红细胞产生的副产物。通过使用合适的催化剂将丙交酯聚合成聚乳酸，可以获得具有多种实用特性的材料。

反应信息

• 作为反应物：
  描述：

  (3R,6R)-3,6-二甲基-1,4-二恶烷-2,5-二酮 在 盐酸 、 对甲苯磺酸 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 Ethyl (2R)-2-((tetrahydro-2H-pyran-2-yl)oxy)propanoate
  参考文献：
  名称：

  Constitutionally Asymmetric and Chiral [2]Pseudorotaxanes¹

  摘要：

  The self-assembly and characterization of a range of chiral pseudorotaxanes has been explored using chiroptical methods. The syntheses of (i) constitutionally asymmetric acyclic hydroquinone-containing polyethers and (ii) optically active hydroquinone-containing acyclic polyethers, bearing pairs of methyl or isobutyl groups related to each other in a C-2-symmetric manner within the polyether backbone, are described. The combination of (i) the tetracationic cyclophane cyclobis(paraquat-p-phenylene) tetrakis(hexafluorophosphate), possessing a pi-electron deficient cavity, and (ii) the linear noncentrosymmetric acyclic polyethers produces [2]pseudorotaxanes that have been characterized by H-1 NMR, UV/vis and circular dichroism (CD) spectroscopies in solution and by X-ray crystallography in the solid state. The introduction of constitutional asymmetry or chirality gives rise to a number of different geometries for the [2]pseudorotaxanes in both the solution and solid states. in particular, CD-spectroscopic measurements on the optically active [2]pseudorotaxanes have shown that-depending on the positions of the C-2 symmetrically related chiral centers in the polyether chains with respect to the hydroquinone rings-the chirality present in the pi-electron rich threadrike guest can induce chirality that is associated with the supramolecular structure as a whole, resulting in a chiral charge-transfer transition involving not only the pi-donors in the chiral guests but also the pi-acceptors in the achiral host.

  DOI：

  10.1021/ja970018i
• 作为产物：
  描述：

  (3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione 在 potassium phosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 220.0h， 生成 (3R,6R)-3,6-二甲基-1,4-二恶烷-2,5-二酮
  参考文献：
  名称：

  Studies on the epimerization of diastereomeric lactides

  摘要：

  The epimerization of chiral lactides was studied in the presence of various homogeneous and heterogeneous bases. Some solvent/base systems were found to promote epimerization at room temperature efficiently. Side reactions such as polymerization were not observed or occurred only slowly. This new protocol offers the opportunity of the transformation of meso-lactide into rac-lactide. Therefore it can reduce the overall manufacturing costs of polylactides, a problem which currently hampers the broad application of those environmentally friendly polymers in a large scale. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.12.094
• 作为试剂：
  描述：

  α-phenyl-β-propiolactone 在 AdTPAZr-R-ML 、 (3R,6R)-3,6-二甲基-1,4-二恶烷-2,5-二酮 作用下， 以 甲苯 为溶剂， 以99.3%的产率得到
  参考文献：
  名称：

  单体促进不对称动力学拆分-交替共聚以提供 AAB 型共聚酯

  摘要：

  混合单体的活性共聚可以通过控制单体和立体序列来丰富具有明确性能的共聚物材料的多样性。然而，在合成高分子科学中，具有两种以上组分的同类型单体的周期性序列控制活性共聚仍然是一个挑战。在这项工作中，一种新的单体促进不对称动力学拆分-交替共聚的方法可以让l-丙交酯（S，S -LA 或l -LA）和外消旋托品酸环酯（托品内酯）的两种对映异构体的三组分混合物聚合成顺序控制的 −(A S A S B S ) n– 类型可生物降解共聚酯（下标 S 表示构型，A 和 B 分别表示乳酸单元和托品酸单元），以及 -(A S A S B S ) n - b - ( A R A R B R ) n – 可以通过添加R,R -LA ( d - LA) 进一步获得。与以前通过聚合或有机反应进行的外消旋化学品的不对称动力学拆分相比，该系统不需要对映体纯催化剂/引发剂。S,S -LA与外消旋拆分交替共聚后-托吡卡内酯，未反应的托吡卡内酯的ee值可达99

  DOI：

  10.1021/jacs.3c01599

文献信息

• CYCLIC CARBONYL COMPOUNDS WITH PENDANT CARBONATE GROUPS, PREPARATIONS THEREOF, AND POLYMERS THEREFROM
  申请人：Fujiwara Masaki

  公开号：US20110269917A1

  公开（公告）日：2011-11-03

  A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl carbonate group is disclosed. The cyclic carbonyl compounds can be polymerized by ring opening methods to form ROP polymers comprising repeat units comprising a side chain pentafluorophenyl carbonate group. Using a suitable nucleophile, the pendant pentafluorophenyl carbonate group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.

  公开了一种制备含有活性吊挂五氟苯基碳酸酯基团的环状羰基化合物的一锅法。这些环状羰基化合物可以通过环开启方法聚合，形成包含侧链五氟苯基碳酸酯基团的ROP聚合物重复单元。使用适当的亲核试剂，可以在环开启聚合之前或之后，选择性地将吊挂的五氟苯基碳酸酯基团转化为各种其他功能基团。
• Manganese‐Catalyzed Hydroborations with Broad Scope
  作者：Pradip Ghosh、Axel Jacobi von Wangelin

  DOI：10.1002/anie.202103550

  日期：2021.7.12

  synthetic manipulation and chemical valorization. The applications of catalytic hydrofunctionalization benefit from the use of liquid reducing agents and operationally facile setups. Metal-catalyzed hydroborations provide a highly prolific platform for reductive valorizations of stable C=X electrophiles. Here, we report an especially facile, broad-scope reduction of various functions including carbonyls

  容易获得的氧化物质的还原转化是合成操作和化学价值化的核心。催化加氢官能化的应用受益于液体还原剂的使用和操作简便的设置。金属催化的硼氢化反应为稳定的 C=X 亲电试剂的还原增值提供了一个高产的平台。在这里，我们报告了在非常温和的条件下，使用廉价的预催化剂 Mn(hmds) 2可以特别轻松、广泛地还原各种功能，包括羰基化合物、羧酸盐、吡啶、碳二亚胺和碳酸盐。该反应可以成功地应用于解聚。
• POLYMERS BEARING PENDANT PENTAFLUOROPHENYL ESTER GROUPS, AND METHODS OF SYNTHESIS AND FUNCTIONALIZATION THEREOF
  申请人：Fujiwara Masaki

  公开号：US20100305281A1

  公开（公告）日：2010-12-02

  A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl ester group is disclosed. The cyclic carbonyl compounds can be polymerized by ring opening methods to form ROP polymers comprising repeat units comprising a side chain pentafluorophenyl ester group. Using a suitable nucleophile, the pendant pentafluorophenyl ester group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.

  揭示了一种制备含有活性吊挂五氟苯基酯基团的环状羰基化合物的一锅法。这些环状羰基化合物可以通过环开启方法聚合，形成包含侧链五氟苯基酯基团的ROP聚合物重复单元。使用适当的亲核试剂，吊挂的五氟苯基酯基团可以在环开启聚合之前或之后选择性地转化为各种其他功能基团。
• [EN] CYCLIC CARBONYL COMPOUNDS WITH PENDANT PENTAFLUOROPHENYL CARBONATE GROUPS, PREPARATIONS THEREOF, AND POLYMERS THEREFROM<br/>[FR] COMPOSÉS CARBONYLÉS CYCLIQUES AVEC GROUPEMENTS PENTAFLUOROPHÉNYLCARBONATE PENDANTS, LEURS SYNTHÈSES ET LEURS POLYMÈRES
  申请人：IBM

  公开号：WO2011135046A1

  公开（公告）日：2011-11-03

  A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl carbonate group is disclosed. The cyclic carbonyl compounds can be polymerized by ring opening methods to form ROP polymers comprising repeat units comprising a side chain pentafluorophenyl carbonate group. Using a suitable nucleophile, the pendant pentafluorophenyl carbonate group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.

  揭示了一种制备含有活性吊挂五氟苯基碳酸酯基团的环状羰基化合物的一锅法。这些环状羰基化合物可以通过环开启方法聚合，形成包含侧链五氟苯基碳酸酯基团的ROP聚合物重复单元。利用适当的亲核试剂，吊挂的五氟苯基碳酸酯基团可以在环开启聚合之前或之后被选择性地转化为各种其他功能基团。
• ANTIMICROBIAL COMPOSITIONS, METHODS OF PREPARATION THEREOF, AND USES THEREOF
  申请人：Coady Daniel J.

  公开号：US20120251607A1

  公开（公告）日：2012-10-04

  A composition of matter comprises a cationic polymer comprising a polycarbonate chain fragment, the polycarbonate chain fragment comprising a repeat unit comprising a side chain moiety containing a quaternary amine group; and a non-charged polymer comprising a polyester chain segment and a poly(alkylene oxide) chain segment; wherein i) the cationic polymer and the non-charged polymer are amphiphilic and biocompatible, ii) the cationic polymer and the non-charged polymer form a mixed complex by non-covalent interactions in water, and iii) the mixed complex is a more effective antimicrobial agent against at least a Gram-negative microbe compared to the cationic polymer and the non-charged polymer alone when tested using otherwise identical conditions.

  一种物质的组成包括阳离子聚合物，该阳离子聚合物包括聚碳酸酯链片段，所述聚碳酸酯链片段包括一个重复单元，所述重复单元包括一个含季铵胺基团的侧链部分；以及一种非带电聚合物，包括聚酯链段和聚（烷基氧化物）链段；其中i）所述阳离子聚合物和非带电聚合物是两性且生物相容的，ii）所述阳离子聚合物和非带电聚合物在水中通过非共价相互作用形成混合复合物，iii）与单独使用时，所述混合复合物在至少一种革兰氏阴性微生物的抗菌剂测试中比阳离子聚合物和非带电聚合物更有效。