7-(1-hydroxy-1-methylethyl)-4-methyl-6,7-dihydrooxepin-2(5H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(1-hydroxy-1-methylethyl)-4-methyl-6,7-dihydrooxepin-2(5H)-one
• 英文别名: 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide；3,7-dimethyl-7-hydroxy-2-octen-6-olide；2-(2-hydroxypropan-2-yl)-5-methyl-3,4-dihydro-2H-oxepin-7-one
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: ICSVRXLISHBJRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(1-hydroxy-1-methylethyl)-4-methyl-6,7-dihydrooxepin-2(5H)-one 在 吡啶 、 氯化亚砜 作用下， 反应 0.25h， 以78.4%的产率得到3,7-dimethyl-2,6-octadien-1,6-olide
  参考文献：
  名称：

  Total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and 3,7-dimethyl-2,6-octadien-1,6-olide

  摘要：

  3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide (1) and 3,7-dimethyl-2,6-octadien-1,6-olide (2), the natural bioactive compounds isolated from the fruit of Litsea cubeba and the liverwort Plagiochila rutilans, were totally synthesized using easily available cis-geraniol as raw material in short, convenient, and low-cost, five-step reactions including three steps of oxidation, cyclization, and dehydration, with an overall yield of 47.5% and 37.3%.

  DOI：

  10.1080/10286020.2013.803474
• 作为产物：
  描述：

  顺式-柠檬醛 在 过氧乙酸 、 sodium chlorite 、 sodium dihydrogenphosphate 、 camphor-10-sulfonic acid 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 12.5h， 生成 7-(1-hydroxy-1-methylethyl)-4-methyl-6,7-dihydrooxepin-2(5H)-one
  参考文献：
  名称：

  Total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and 3,7-dimethyl-2,6-octadien-1,6-olide

  摘要：

  3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide (1) and 3,7-dimethyl-2,6-octadien-1,6-olide (2), the natural bioactive compounds isolated from the fruit of Litsea cubeba and the liverwort Plagiochila rutilans, were totally synthesized using easily available cis-geraniol as raw material in short, convenient, and low-cost, five-step reactions including three steps of oxidation, cyclization, and dehydration, with an overall yield of 47.5% and 37.3%.

  DOI：

  10.1080/10286020.2013.803474

文献信息

• Synthesis of epoxy dinitriles from citral and their acid-catalyzed transformations
  作者：K. P. Volcho、O. I. Yarovaya、S. Yu. Kurbakova、D. V. Korchagina、V. A. Barkhash、N. F. Salakhutdinov

  DOI：10.1134/s1070428007040045

  日期：2007.4

  2,3-and 6,7-Epoxy derivatives of citral react with malononitrile in the presence of basic Cs beta-zeolite to give the corresponding epoxyalkenylidenemalononitriles as the major products. Epoxy dinitriles obtained from 6,7-epoxycitral undergo acid-catalyzed transformations into tetrahydrofuran derivatives or acyclic polyenes containing hydroxy and cyano groups, depending on the catalyst nature.
• Total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and 3,7-dimethyl-2,6-octadien-1,6-olide
  作者：Hong-Bo Dong、Ming-Yan Yang、Jia-Zheng Jiang、Ming-An Wang

  DOI：10.1080/10286020.2013.803474

  日期：2013.8

  3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide (1) and 3,7-dimethyl-2,6-octadien-1,6-olide (2), the natural bioactive compounds isolated from the fruit of Litsea cubeba and the liverwort Plagiochila rutilans, were totally synthesized using easily available cis-geraniol as raw material in short, convenient, and low-cost, five-step reactions including three steps of oxidation, cyclization, and dehydration, with an overall yield of 47.5% and 37.3%.