2-[(2R,3S)-3-prop-2-enoxyoxan-2-yl]acetaldehyde | 208454-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[(2R,3S)-3-prop-2-enoxyoxan-2-yl]acetaldehyde
• CAS: 208454-48-2
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: XKNGLXADJGPJBI-VHSXEESVSA-N

物化性质

• 沸点：
  280.0±25.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2R,3S)-3-prop-2-enoxyoxan-2-yl]acetaldehyde 在 2,6-二甲基吡啶 、 lead(IV) acetate 、 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 草酰氯 、 仲丁基锂 、 四氯化钛 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 2.41h， 生成
  参考文献：
  名称：

  A Convergent Synthesis of the Decacyclic Ciguatoxin Model Containing the F−M Ring Framework

  摘要：

  A highly convergent synthesis of the decacyclic ciguatoxin model 2, which contains the F-M ring framework of the natural product, has been achieved through the assembly of pentacyclic oxonane 4 and JKLM ring fragment 5. The two key steps in the synthesis of the former compound are (i) a Lewis acid-mediated intramolecular reaction of a gamma-alkoxyallylsilane with an acetal group to form an O-linked oxacycle and (ii) a SmI2-mediated intramolecular Reformatsky reaction leading to construction of the annelated oxonane ring system. Preliminary biological investigations revealed that model compound 2 did not inhibit the binding of tritium-labeled dihydrobrevetoxin B to voltage-sensitive sodium channels at micromolar concentrations.

  DOI：

  10.1021/jo990989b
• 作为产物：
  描述：

  (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到2-[(2R,3S)-3-prop-2-enoxyoxan-2-yl]acetaldehyde
  参考文献：
  名称：

  The tert-butyl dimethyl silyl group as an enhancer of drug cytotoxicity against human tumor cells

  摘要：

  In this study, we synthesized a series of enantiomerically pure (2R,3S)-disubstituted tetrahydropyranes with diverse functional groups using known methodologies. In addition to the tert-butyl dimethyl silyl group, other common protecting groups for hydroxyl groups such as allyl, acetate, and benzoate were used to obtain appropriate derivatives. Pure compounds were evaluated in vitro against HL60 human leukemia cells and MCF7 human breast cancer cells. From the growth inhibition data a structure-activity relationship was obtained. Overall the results point to the relevant role of the tert-butyl dimethyl silyl group in the modulation of cytotoxic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.126