t-butyl 2,7-dimethyl-6-octenoate | 325465-75-6

• 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: t-butyl 2,7-dimethyl-6-octenoate
• 英文别名: Tert-butyl 2,7-dimethyloct-6-enoate
• CAS: 325465-75-6
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: LKPYLJILEZGTLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  t-butyl 2,7-dimethyl-6-octenoate 在 9-borabicyclo[3.3.1]nonane dimer 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.25h， 生成 t-butyl 2,7-dimethyl-2-(3-hydroxypropyl)-6-octenoate
  参考文献：
  名称：

  Further Studies of the Daphniphyllum Alkaloid Polycyclization Cascade

  摘要：

  The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 8-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade.

  DOI：

  10.1021/jo001145r
• 作为产物：
  描述：

  5-甲基-4-己烯-1-醇 在 咪唑 、 碘 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.25h， 生成 t-butyl 2,7-dimethyl-6-octenoate
  参考文献：
  名称：

  Further Studies of the Daphniphyllum Alkaloid Polycyclization Cascade

  摘要：

  The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 8-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade.

  DOI：

  10.1021/jo001145r

文献信息

• Synthetic studies toward longeracemine: The intramolecular [4+2] cycloaddition of 3H-pyrroles
  作者：Joshua B. Cox、John L. Wood

  DOI：10.1016/j.tet.2018.07.024

  日期：2018.8

  Model studies to develop a tetracyclization approach mimicking the proposed biosynthesis of the secodaphnane-type alkaloid longeracemine are described. These studies have culminated in the successful implementation of a 3H-pyrrole [4+2] cycloaddition that delivers a longeracemine-like azabicycle containing three contiguous quaternary stereocenters.

  描述了开发四环化方法的模型研究，该方法模拟拟议中的苏打法烷型生物碱长乙胺的生物合成。这些研究最终成功地实现了3 H-吡咯[4 + 2]环加成反应，该环加成反应产生了一个包含三个连续的四级立体中心的类似长乙胺的氮杂双环。
• Further Studies of the <i>Daphniphyllum</i> Alkaloid Polycyclization Cascade
  作者：Grier A. Wallace、Clayton H. Heathcock

  DOI：10.1021/jo001145r

  日期：2001.1.1

  The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 8-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade.