(2S,4R)-6-heptene-1,2,4-triol | 114092-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,4R)-6-heptene-1,2,4-triol
• 英文别名: (2S,4R)-hept-6-ene-1,2,4-triol
• CAS: 114092-19-2
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: JDLWOLSYKQUULO-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R)-6-heptene-1,2,4-triol 在 咪唑 、 sodium hydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 ((4S,6R)-6-Allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-methanol
  参考文献：
  名称：

  Studies on the Stereochemistry of Theonezolides A-C: Elucidation of the Relative Configurations of 1,3-Diol Moieties of the C-4Å`C-17 Fragment

  摘要：

  Four model compounds having syn and anti 1,3-diol type moieties corresponding to C-8/C-10 and C-14/C-16 positions contained in the C-4 similar to C-17 fragment of theonezolides A-C were prepared. Comparison of their spectral data suggested that the 1,3-diol at C-8/C-10 and the OH/OMe groups at C-14/C-16 positions of theonezolides A-C were both syn.

  DOI：

  10.3987/com-97-s6-1
• 作为产物：
  描述：

  (4S)-2,2-二甲基-1,3-二氧戊环-4-乙醛 在 甲醇 、 氢氧化钾 、 Amberlite IR-120(H⁽¹⁺⁾) 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙醚 、 水 、 甲苯 为溶剂， 反应 19.75h， 生成 (2S,4R)-6-heptene-1,2,4-triol
  参考文献：
  名称：

  Kocienski, Philip J.; Yeates, Clive; Street, Stephen D. A., Journal of the Chemical Society. Perkin transactions I, 1987, p. 2183 - 2188

  摘要：

  DOI：

文献信息

• A difference CD method for determining absolute stereochemistry of acyclic 1,2,4-triols
  作者：Yuji Mori、Hiroshi Furukawa

  DOI：10.1016/0040-4020(95)00329-7

  日期：1995.6

  A general method based on difference circular dichroic (DIF CD) spectroscopy for assigning the absolute configuration of 1,2,4-triol is presented. Four possible stereoisomers of 6-heptene-1,2,4-triol were prepared and served as models to develop the procedure. The sign of the DIF CD Cotton effect is correlated to the absolute configuration of the C2 position.

  提出了一种基于差圆二向色（DIF CD）光谱法确定1,2,4-三醇绝对构型的通用方法。制备了四种可能的6-庚烯-1,2,4-三醇立体异构体，并将其用作开发该方法的模型。DIF CD棉花效应的迹象与C2位置的绝对构型相关。
• Synthesis of a spiroacetal moiety of antitumor antibiotic ossamycin by anodic oxidation
  作者：Eriko Honjo、Noriki Kutsumura、Yuichi Ishikawa、Shigeru Nishiyama

  DOI：10.1016/j.tet.2008.07.078

  日期：2008.9

  Synthesis of the spiroacetal moiety (C20–C33) of the antitumor antibiotic ossamycin, is reported. Anodic oxidation of the dithioacetal effected simultaneous removal of the protecting group and acetalization to afford the corresponding 6,6-spiroacetal structure in excellent yield.

  据报道合成了抗肿瘤抗生素奥沙霉素的螺缩醛部分（C20-C33）。二硫缩醛的阳极氧化实现了保护基团的同时去除和缩醛化，从而以优异的产率提供了相应的6，6-螺缩醛结构。
• A differential CD method for assigning absolute stereochemistry of 1, 2, 4-triols
  作者：Yuji Mori、Yasunori Kohchi、Makoto Suzuki、Hiroshi Furukawa

  DOI：10.1016/0040-4039(92)88132-o

  日期：1992.4

  A simple method for assigning the absolute configuration of benzoate derivatives of 1, 2, 4-triols have been established using a differential CD exiton chirality method.

  使用差速CD出口手性法已经建立了一种简单的方法来确定1,2,4-三醇的苯甲酸酯衍生物的绝对构型。
• Synthesis of A-ring fragments of 1α,25-dihydroxyvitamin D3 and taxane diterpenoids: Effective construction of conjugated formylcyclohexene frameworks from isoxazolines
  作者：Teruhiko Ishikawa、Shushiro Ikeda、Masataka Ibe、Seiki Saito

  DOI：10.1016/s0040-4020(98)00273-7

  日期：1998.5

  This paper have delineated the effectiveness of [3+2] cycloaddition process in the synthesis of multifunctional 6-membered rings. The novel synthesis of chiral A-ring fragment of 1 alpha,25-dihydroxyvitamin D-3 and also a novel route to A-ring fragment of taxane diterpenoids have been established. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols
  作者：Makhosazana P. Gamedze、Comfort M. Nkambule

  DOI：10.1016/j.tetlet.2015.02.083

  日期：2015.4

  Dibutyltin oxide (Bu2SnO) mediated cyclodehydration or sulfonylation of 1,2,4-triols is predictably diastereoselective depending on the steric bulk of the substituents at C4. A larger difference (Delta A-value >1 kcal/mol) leads to the syn-1,2,4-triols favouring cyclodehydration (78-85%) to form 3-hydroxytetrahydrofurans, with the anti-1,2,4-triols favouring monosulfonylation (66-87%). Triols from symmetrical ketones preferentially undergo cyclodehydration in high yield (>75%) due to a gem-disubstituent effect. Thus, the 1,2,4-triols derived from simple cyclic ketones also favour cyclodehydration to form spirocyclic 3-hydroxytetrahydrofurans in 72-79% yields. (C) 2015 Elsevier Ltd. All rights reserved.