decan-1,5-diol | 4203-48-9

• 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: decan-1,5-diol
• 英文别名: decane-1,5-diol；1,5-decanediol
• CAS: 4203-48-9
• 化学式: C₁₀H₂₂O₂
• 分子量: 174.283
• InChiKey: BMHXYCAVLBMDOD-UHFFFAOYSA-N

物化性质

• 熔点：
  23-24 °C
• 沸点：
  162 °C(Press: 10 Torr)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  decan-1,5-diol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以73%的产率得到1,5-Dibromodecane
  参考文献：
  名称：

  Polychlorinated Acetamides from the Cyanobacterium Microcoleus lyngbyaceus

  摘要：

  Several new compounds were isolated from the organic extract of the cyanobacterium Microcolcus lyngbyaceus, and their structures were determined by spectroscopic means. Polychlorinated acetamidoalkynes and alkanes were the major metabolites. 6-Acetamido-1,1,1-trichloroundccane, a positional isomer of the naturally occurring 5-acetamido-1,1,1-trichloroundecane, was synthesized in six steps from 6-decanolactone.

  DOI：

  10.1021/np000452p
• 作为产物：
  描述：

  1,5-Dibromodecane 在 silver nitrate 、 溶剂黄146 作用下， 生成 decan-1,5-diol
  参考文献：
  名称：

  Studien �ber 1,4- und 1,5-Oxidoverbindungen

  摘要：

  DOI：

  10.1007/bf01518111

文献信息

• Electron transfer reduction of unactivated esters using SmI2–H2O
  作者：Michal Szostak、Malcolm Spain、David J. Procter

  DOI：10.1039/c1cc14014k

  日期：——

  The reduction of unactivated esters using samarium diiodide is reported for the first time. The optimised protocol allows for the reduction of primary, secondary and tertiary alkyl esters in excellent yields and is competitive with reductions mediated by metal hydrides and alkali metals.

  首次报道了使用二碘化sa还原未活化的酯。优化的方案可以以优异的产率还原伯，仲和叔烷基酯，并且与金属氢化物和碱金属介导的还原反应具有竞争力。
• Hydrogenation of Esters to Alcohols with a Well-Defined Iron Complex
  作者：Svenja Werkmeister、Kathrin Junge、Bianca Wendt、Elisabetta Alberico、Haijun Jiao、Wolfgang Baumann、Henrik Junge、Fabrice Gallou、Matthias Beller

  DOI：10.1002/anie.201402542

  日期：2014.8.11

  We present the first base‐free Fe‐catalyzed ester reduction applying molecular hydrogen. Without any additives, a variety of carboxylic acid esters and lactones were hydrogenated with high efficiency. Computations reveal an outer‐sphere mechanism involving simultaneous hydrogen transfer from the iron center and the ligand. This assumption is supported by NMR experiments.

  我们展示了第一个使用分子氢的无碱铁催化的酯还原反应。在没有任何添加剂的情况下，各种羧酸酯和内酯被高效地氢化。计算揭示了一种外球机理，涉及同时从铁中心和配体转移氢。NMR实验支持这一假设。
• ATP3 and MTP3: Easily Prepared Stable Perruthenate Salts for Oxidation Applications in Synthesis
  作者：Peter W. Moore、Christopher D. G. Read、Paul V. Bernhardt、Craig M. Williams

  DOI：10.1002/chem.201800531

  日期：2018.3.26

  commercial catalyst supply. However, the mild instability of TPAP creates preparation, storage, and reaction reproducibility issues, due to unpreventable slow decomposition. In search of attributes conducive to catalyst longevity an extensive range of novel perruthenate salts were prepared. Subsequent evaluation unearthed a set of readily synthesized, bench stable, phosphonium perruthenates (ATP3 and

  该魔网格里菲斯四ñ丙基过钌酸铵（TPAP）催化剂已被合成界广泛采用，主要用于将醇氧化为醛和酮，还用于多种其他合成转化（例如二醇裂解，异构化，亚胺形成和杂环合成）。在广泛的反应范围，官能团耐受性，温和条件和商业催化剂供应上已经锻造了这种受欢迎度。但是，由于无法防止的缓慢分解，TPAP的轻度不稳定会导致制备，储存和反应重现性问题。为了寻找有利于催化剂寿命的属性，制备了多种新颖的过硼酸盐。随后的评估发现了一组易于合成，稳定的台式过氧化磷鎓（ATP3和MTP3），它们反映了TPAP的反应活性，
• Secondary Amides as Hydrogen Atom Transfer Promoters for Reactions of Samarium Diiodide
  作者：Tesia V. Chciuk、Anna M. Li、Andres Vazquez-Lopez、William R. Anderson、Robert A. Flowers

  DOI：10.1021/acs.orglett.6b03664

  日期：2017.1.6

  Two secondary amides (N-methylacetamide and 2-pyrrolidinone) were used as additives with SmI2 in THF to estimate the extent of N–H bond weakening upon coordination. Mechanistic and synthetic studies demonstrate significant bond-weakening, providing a reagent system capable of reducing a range of substrates through formal hydrogen atom transfer.

  两种仲酰胺（N-甲基乙酰胺和2-吡咯烷酮）与SmI 2在THF中的添加剂一起使用，以评估配位时N–H键减弱的程度。机械和合成研究表明，键的弱化作用显着，它提供了一种试剂系统，能够通过正式的氢原子转移来减少一系列底物。
• Mechanistic study of the samarium diiodide—N,N-dimethyl-2-aminoethanol reducing system
  作者：Tesia V. Chciuk、Brian P. Boland、Robert A. Flowers

  DOI：10.1016/j.tetlet.2014.12.095

  日期：2015.6

  N-dimethyl-2-aminoethanol (DMAE) on the reactivity of SmI2 is presented. The SmI2–DMAE reagent system is capable of reducing a range of substrates including alkyl halides, ketones, lactones, and arenes. Mechanistic studies on anthracene reduction are consistent with a system that proceeds through a highly ordered, early transition state requiring 2 equiv of DMAE and 1 equiv of anthracene and Sm(II).

  提出了N，N-二甲基-2-氨基乙醇（DMAE）对SmI 2反应性的影响。SmI 2 –DMAE试剂系统能够减少多种底物，包括卤代烷，酮，内酯和芳烃。减少蒽的机理研究与通过高度有序的，早期过渡状态进行的系统一致，该状态需要2当量的DMAE和1当量的蒽和Sm（II）。