(S)-5-(methoxymethoxy)cyclohex-2-enone | 875926-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-(methoxymethoxy)cyclohex-2-enone
• 英文别名: (5S)-5-(methoxymethoxy)cyclohex-2-en-1-one
• CAS: 875926-26-4
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: MNXLHFGJLBLPPU-QMMMGPOBSA-N

物化性质

• 沸点：
  232.5±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (S)-5-(methoxymethoxy)cyclohex-2-enone 在 manganese(IV) oxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.17h， 生成 (5aS,6R,13aS,14R,17S,18R,19R,20S)-7,15-dihydroxy-3,11-dimethoxy-1,9,17,20-tetrakis(methoxymethoxy)-14-hydro-5H,6H-6,13a,5a,14-(epibutane[1,2,3,4]tetrayl)cycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16-tetraone
  参考文献：
  名称：

  通过级联反应完全合成（+）-果胶素和（+）-2,2'-表-细胞skyrinA。

  摘要：

  DOI：

  10.1002/anie.200503678
• 作为产物：
  描述：

  cis,cis-3-hydroxy-5-methyl-carbonyloxy-cyclohexyl acetate 在 porcine liver esterase 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 phosphate buffer 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 12.67h， 生成 (S)-5-(methoxymethoxy)cyclohex-2-enone
  参考文献：
  名称：

  Total Syntheses of 2,2‘-epi-Cytoskyrin A, Rugulosin, and the Alleged Structure of Rugulin

  摘要：

  The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.

  DOI：

  10.1021/ja0685708

文献信息

• Total Synthesis of (+)-Rugulosin and (+)-2,2′-epi-Cytoskyrin A through Cascade Reactions
  作者：K. C. Nicolaou、Yee Hwee Lim、Charles D. Papageorgiou、Jared L. Piper

  DOI：10.1002/anie.200503678

  日期：2005.12.9
• Total Syntheses of 2,2‘-<i>epi</i>-Cytoskyrin A, Rugulosin, and the Alleged Structure of Rugulin
  作者：K. C. Nicolaou、Yee Hwee Lim、Jared L. Piper、Charles D. Papageorgiou

  DOI：10.1021/ja0685708

  日期：2007.4.1

  The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.