2,2-dimethyl-5-{3-[(tert-butyldimethylsilyloxy)methyl]but-3-en-1-ylidene}-1,3-dioxan | 1234793-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-{3-[(tert-butyldimethylsilyloxy)methyl]but-3-en-1-ylidene}-1,3-dioxan
• 英文别名: Tert-butyl-[4-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-methylidenebutoxy]-dimethylsilane
• CAS: 1234793-85-1
• 化学式: C₁₇H₃₂O₃Si
• 分子量: 312.525
• InChiKey: NXUPCDVNAIZAMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-{3-[(tert-butyldimethylsilyloxy)methyl]but-3-en-1-ylidene}-1,3-dioxan 在 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到2-(hydroxymethyl)-5-methylenehex-2-ene-1,6-diol
  参考文献：
  名称：

  Efficient construction of the core framework of lysidicin A via three Claisen rearrangements including a cascade reaction

  摘要：

  A model compound (6) with the core skeleton of lysidicin A was synthesized as a racemate. The key step (8,7) includes three Claisen rearrangements of the triether with phloroglucinols; two of which rearranged in a cascade manner and the other was a simple rearrangement. This one-pot reaction enabled the introduction of three phloroglucinol units at the correct positions and makes the synthetic approach significantly efficient. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.073
• 作为产物：
  描述：

  2-methylenebutane-1,4-diol 在 咪唑 、 正丁基锂 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 乙腈 、 mineral oil 为溶剂， 反应 2.75h， 生成 2,2-dimethyl-5-{3-[(tert-butyldimethylsilyloxy)methyl]but-3-en-1-ylidene}-1,3-dioxan
  参考文献：
  名称：

  Total synthesis of (±)-lysidicin A

  摘要：

  Lysidicin A, which has been isolated from Lisidicie rhodostegia possesses complicated structure. A total synthesis of lysidicin A has been achieved and is described herein. The key reaction is single and cascade Claisen rearrangements. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.062

文献信息

• Efficient construction of the core framework of lysidicin A via three Claisen rearrangements including a cascade reaction
  作者：Yusuke Ogura、Hidenori Watanabe

  DOI：10.1016/j.tetlet.2010.04.073

  日期：2010.6

  A model compound (6) with the core skeleton of lysidicin A was synthesized as a racemate. The key step (8,7) includes three Claisen rearrangements of the triether with phloroglucinols; two of which rearranged in a cascade manner and the other was a simple rearrangement. This one-pot reaction enabled the introduction of three phloroglucinol units at the correct positions and makes the synthetic approach significantly efficient. (C) 2010 Elsevier Ltd. All rights reserved.
• Total synthesis of (±)-lysidicin A
  作者：Yusuke Ogura、Ken Ishigami、Hidenori Watanabe

  DOI：10.1016/j.tet.2011.12.062

  日期：2012.2

  Lysidicin A, which has been isolated from Lisidicie rhodostegia possesses complicated structure. A total synthesis of lysidicin A has been achieved and is described herein. The key reaction is single and cascade Claisen rearrangements. (C) 2011 Elsevier Ltd. All rights reserved.