4-hexyl-2,2,5-trimethyl-[1,3]dioxane | 540481-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hexyl-2,2,5-trimethyl-[1,3]dioxane
• 英文别名: (4R,5S)-4-Hexyl-2,2,5-trimethyl-1,3-dioxane
• CAS: 540481-97-8
• 化学式: C₁₃H₂₆O₂
• 分子量: 214.348
• InChiKey: XCPZNJSVOPOVSS-NWDGAFQWSA-N

物化性质

• 沸点：
  233.9±8.0 °C(Predicted)
• 密度：
  0.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (2S,3R)-3-Methoxymethoxy-2-methyl-nonan-1-ol 在 盐酸 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-hexyl-2,2,5-trimethyl-[1,3]dioxane
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036

文献信息

• Total synthesis and NMR conformational study of signal peptidase II inhibitors, globomycin and SF-1902 A5
  作者：Toshihiro Kiho、Mizuka Nakayama、Hiroshi Kogen

  DOI：10.1016/s0040-4020(03)00110-8

  日期：2003.3

  A stereoselective total synthesis of an antibiotic, globomycin (1a), and its congener, SF-1902 A5 (1b), was achieved. Two convergent macrocyclization routes via macrolactamization or macrolactonization to form 1a are described. A conformational study by means of NMR spectroscopy was performed in several solvents. The 1H NMR spectrum of 1a indicated that the amide proton of only the l-allo-Thr residue

  立体选择性地合成了抗生素球蛋白（1a）及其同类物SF-1902 A 5（1b）。描述了通过大内酰胺化或大内酰胺化形成1a的两种会合大环化途径。在几种溶剂中通过NMR光谱进行了构象研究。1a的1 H NMR光谱表明，只有l- allo -Thr残基的酰胺质子与氢键有关。溶液相的结构不同于X射线的结构。
• Surprising Role of Aryl Halides in Nickel-Catalyzed Reductive Aldol Reactions
  作者：Christa C. Chrovian、John Montgomery

  DOI：10.1021/ol063028+

  日期：2007.2.1

  [reaction: see text] A new nickel-catalyzed method for the reductive aldol addition of acrylates and aldehydes has been developed. An unexpected requirement for an aryl iodide additive was found in the process, and the effect was shown to be linked to an initiation step.

  [反应：见正文]已经开发了一种新的镍催化的丙烯酸酯和醛的醛醇缩合加成方法。在该方法中发现了对芳基碘化物添加剂的出乎意料的要求，并且显示出该效果与引发步骤有关。