2,4:3,5-dimethylene-D-mannitol | 73209-88-8

• 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: 2,4:3,5-dimethylene-D-mannitol
• 英文别名: 2,4:3,5-di-O-methylene-D-mannitol；O²,O⁴;O³,O⁵-dimethanediyl-D-mannitol；O²,O⁴;O³,O⁵-Dimethandiyl-D-mannit；((4R,4aR,8R,8aR)-Tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4,8-diyl)dimethanol；[(4R,4aR,8R,8aR)-4-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-8-yl]methanol
• CAS: 73209-88-8
• 化学式: C₈H₁₄O₆
• 分子量: 206.196
• InChiKey: DLIMVTKZIGEWCB-WCTZXXKLSA-N

物化性质

• 熔点：
  260-262 °C (decomp)
• 沸点：
  368.6±37.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4:3,5-dimethylene-D-mannitol 在 吡啶 、 4-二甲氨基吡啶 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 4,8-dimethyl-1,3,5,7-cis-tetraoxadecalin
  参考文献：
  名称：

  Substituent effects on the conformational equilibrium of 1,3,5,7-cis-tetraoxadecalin systems: Force field calculations Versus experimental results

  摘要：

  Conformer populations of a number of 1,3,5,7-cis-tetraoxadecalins have been studied by H-1 NMR spectroscopy. While the unsubstituted 4 prefers the proximal conformation, all 4,8 disubstituted derivatives 5 preferred the distal conformation. This was most marked for the di-azidomethyl derivative 5g. Force field calculations were shown to reproduce only roughly the trends of the conformer equilibria. Changing the solvent from toluene-D-8 to more polar solvents increases the population of the proximal conformer.

  DOI：

  10.1016/0957-4166(95)00366-w
• 作为产物：
  描述：

  甘露醇 在 吡啶 、 硫酸 、 sodium 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 2,4:3,5-dimethylene-D-mannitol
  参考文献：
  名称：

  Bio-Based Aromatic Polyesters from a Novel Bicyclic Diol Derived from d-Mannitol

  摘要：

  2,4:3,5-Di-O-methylene-D-mannitol, abbreviated as Manx, is a D-mannitol-derived compound with the secondary hydroxyl groups acetalized with formaldehyde. The bicyclic structure of Manx consists of two fused 1,3-dioxane rings, with two primary hydroxyl groups standing free for reaction. A homopolyester made of Manx and dimethyl terephthalate as well as a set of copolyesters of poly(butylene terephthalate) (PBT) in which 1,4-butanediol was replaced by Manx up to 50% were synthesized and characterized. The polyesters had M-w in the 30 000-52 000 g mol(-1) range and a random microstructure and were thermally stable up to nearly 370 degrees C. They displayed outstanding high T-g with values from 55 to 137 degrees C which steadily increased with the content in Manx. Copolyesters containing up to 40% of Manx were semicrystalline and adopted the crystal structure of PBT. Their stress-strain parameters were sensitively affected by the presence of carbohydrate-based units with elongation at break decreasing but tensile strength and elastic moduli steadily increasing with the degree of replacement.

  DOI：

  10.1021/ma3013288

文献信息

• Polyesters comprising 2,5-furandicarboxylate and saturated diol units having a high glass transition temperature
  申请人：Furanix Technologies B.V.

  公开号：US10316140B2

  公开（公告）日：2019-06-11

  A polyester including at least one furandicarboxylate unit, at least one saturated, linear or branched, diol unit including from 2 to 10 carbon atoms, and at least one bicyclic diol unit, the said bicyclic diol being chosen from: isosorbide, isoidide, isomannide, 2,3:4,5-di-O-methylene-galactitol, and 2,4:3,5-di-O-methylene-D-mannitol. The glass transition temperature of the polyester is greater than or equal to 90° C. Processes for preparing this polyester are also described.

  一种聚酯，包括至少一个呋喃二甲酸酯单元、至少一个饱和、线性或支链二元醇单元（包括 2 至 10 个碳原子）和至少一个双环二元醇单元，所述双环二元醇选自：异山梨醇、异酰胺、异甘露醇、2,3:4,5-二-O-亚甲基-半乳糖醇和 2,4:3,5-二-O-亚甲基-D-甘露醇。聚酯的玻璃化温度大于或等于 90 摄氏度。
• Haskins; Hann; Hudson, Journal of the American Chemical Society, 1943, vol. 65, p. 73
  作者：Haskins、Hann、Hudson

  DOI：——

  日期：——
• Haworth et al., Journal of the Chemical Society, 1946, p. 488,491
  作者：Haworth et al.

  DOI：——

  日期：——
• 23. The dibenzoates of sorbitol and mannitol and their methylene derivatives
  作者：W. N. Haworth、L. F. Wiggins

  DOI：10.1039/jr9440000058

  日期：——
• Solid-state photooligomerization of an extended chiral bifunctional monomer, (+)-2,4:3,5-di-O-methylene-D-mannitol 1,6-di-trans-cinnamate
  作者：Joel Bernstein、Bernard S. Green、Miriam Rejto

  DOI：10.1021/ja00521a051

  日期：1980.1