3-(hydroxymethyl)pentitol | 65997-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(hydroxymethyl)pentitol
• 英文别名: 3-hydroxymethyl xylitol
• CAS: 65997-86-6
• 化学式: C₆H₁₄O₆
• 分子量: 182.174
• InChiKey: VIQLKPMMHCXYIW-FMCRUOTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.58
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  121.38
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以95%的产率得到3-(hydroxymethyl)pentitol
  参考文献：
  名称：

  Short Synthesis of 3-(Hydroxymethyl)xylitol and Structure Revision of the Anti-diabetic Natural Product from Casearia esculenta

  摘要：

  3-(Hydroxymethyl)xylitol, a compound reportedly isolated from the root of Casearia esculenta (Roxb.), along with its three possible stereoisomers, has been synthesized for the first time by way of a triple dihydroxylation reaction performed upon the simplest cross-conjugated hydrocarbon, [3]dendralene. The data for the natural product do not match any of the isomeric 3-(hydroxymethyl)pentitols. The structure of the natural product from the root of Casearia esculenta (Roxb.) has been corrected by reanalysis of the published data.

  DOI：

  10.1021/ol402740m

文献信息

• Formose Reactions. XIV. A Selective Formose Reaction in the Presence of a Slight Amount of Calcium Ions
  作者：Yoshihiro Shigemasa、Tsuyoshi Taji、Eiichi Waki、Ruka Nakashima

  DOI：10.1246/bcsj.54.1403

  日期：1981.5

  important factor in obtaining the selective formation of the three-branched sugar alcohols. Under these reaction conditions, the α,β-enediol structure is required in an effective co-catalyst for the formose reaction. 2-(Hydroxymethyl)glycerol, 3-(hydroxymethyl)pentitol, and 2,4-bis(hydroxymethyl)pentitol were formed with a high selectivity in the formose reactions catalyzed by KOH, Mg(OH)2, Fe(OH)3

  发现在少量钙和 D-果糖存在下的甲糖反应产生三种产物，2-（羟甲基）甘油、3-（羟甲基）戊醇和 2,4-双（羟甲基）戊醇，具有高选择性。还讨论了影响选择性的各种因素：[Ca]、pH、[D-果糖]、反应温度、助催化剂和金属氢氧化物。相对于 [Ca] 的甲醛量是获得三支链糖醇选择性形成的最重要因素。在这些反应条件下，甲糖反应的有效助催化剂需要α,β-烯二醇结构。2-(羟甲基)甘油、3-(羟甲基)戊醇和2,4-双(羟甲基)戊醇在KOH、Mg(OH)2、Fe(OH)3催化的甲糖反应中以高选择性形成，和氢氧化锂。
• Short Synthesis of 3-(Hydroxymethyl)xylitol and Structure Revision of the Anti-diabetic Natural Product from <i>Casearia esculenta</i>
  作者：Ruomeng Wang、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1021/ol402740m

  日期：2013.11

  3-(Hydroxymethyl)xylitol, a compound reportedly isolated from the root of Casearia esculenta (Roxb.), along with its three possible stereoisomers, has been synthesized for the first time by way of a triple dihydroxylation reaction performed upon the simplest cross-conjugated hydrocarbon, [3]dendralene. The data for the natural product do not match any of the isomeric 3-(hydroxymethyl)pentitols. The structure of the natural product from the root of Casearia esculenta (Roxb.) has been corrected by reanalysis of the published data.