(3R,6R)-3,6-dimethyl-1,4-dioxan-2-one

• 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,6R)-3,6-dimethyl-1,4-dioxan-2-one
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: SGSYSCRIHDTQGZ-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乳酸乙酯 、 (R)-(+)-环氧丙烷 在 5,10,15,20-tetraphenylporphyrin chromium chloride 、 双(三苯基正膦基)氯化铵 作用下， 反应 6.0h， 以58%的产率得到(3R,6S)-3,6-dimethyl-1,4-dioxan-2-one
  参考文献：
  名称：

  Coupling of Propylene Oxide and Lactide at a Porphyrin Chromium(III) Center

  摘要：

  5,10,15,20-Tetraphenylporphyrin chromium chloride (TPPCrCl) with added [Ph3P-N-PPh3]Cl+ (PPN+Cl) selectively polymerizes lactide (l and rac) dissolved in neat propylene oxide (PO) to yield polylactide (PLA) terminated by the -OCHMeCH2Cl group. At 0 degrees C and below, rac-LA yields polymers highly enriched in isotactic tetrads (iii). At 25 degrees C, some stereoselectivity is lost as transesterification becomes significant, and at 60 degrees C and above, enchainment of PO leads to the formation of 3,6-dimethyl-1,4-dioxan-2-one by a backbiting mechanism. At 0 degrees C, after the enchainment of l-(S,S)-LA in neat (R)-(+)-PO, the formation of (3S,6R)-3,6-dimethyl-1,4-dioxan-2-one occurs, while at higher temperatures the ratio of (3S,6R)-3,6-dimethyl-1,4-dioxan-2-one to (3R,6R)-3,6-dimethyl-1,4-dioxan-2-one falls to 3:2.

  DOI：

  10.1021/ja512554t

文献信息

• Coupling of Propylene Oxide and Lactide at a Porphyrin Chromium(III) Center
  作者：Vagulejan Balasanthiran、Chandrani Chatterjee、Malcolm H. Chisholm、Nicole D. Harrold、T. V. RajanBabu、Grant A. Warren

  DOI：10.1021/ja512554t

  日期：2015.2.11

  5,10,15,20-Tetraphenylporphyrin chromium chloride (TPPCrCl) with added [Ph3P-N-PPh3]Cl+ (PPN+Cl) selectively polymerizes lactide (l and rac) dissolved in neat propylene oxide (PO) to yield polylactide (PLA) terminated by the -OCHMeCH2Cl group. At 0 degrees C and below, rac-LA yields polymers highly enriched in isotactic tetrads (iii). At 25 degrees C, some stereoselectivity is lost as transesterification becomes significant, and at 60 degrees C and above, enchainment of PO leads to the formation of 3,6-dimethyl-1,4-dioxan-2-one by a backbiting mechanism. At 0 degrees C, after the enchainment of l-(S,S)-LA in neat (R)-(+)-PO, the formation of (3S,6R)-3,6-dimethyl-1,4-dioxan-2-one occurs, while at higher temperatures the ratio of (3S,6R)-3,6-dimethyl-1,4-dioxan-2-one to (3R,6R)-3,6-dimethyl-1,4-dioxan-2-one falls to 3:2.