(2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile | 234111-49-0

• 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'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile
• 英文别名: 2-[(2R,3S)-3-prop-2-enoxyoxan-2-yl]acetonitrile
• CAS: 234111-49-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: CGOKFTFUAUHGLM-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,3S)-2-hydroxymethyltetrahydropyran-3-ol 在 4-二甲氨基吡啶 、 四丁基碘化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile
  参考文献：
  名称：

  Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles

  摘要：

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

  DOI：

  10.1021/jo9901438