methyl 2,3-dideoxy-4-O-<3-(1-hydroxy-2-methoxy-3-phenyl-4-oxo-2-cyclobuten-1-yl)-2-propynyl>-6-O--α-D-erythro-hex-2-enopyranoside | 171973-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2,3-dideoxy-4-O-<3-(1-hydroxy-2-methoxy-3-phenyl-4-oxo-2-cyclobuten-1-yl)-2-propynyl>-6-O--α-D-erythro-hex-2-enopyranoside
• 英文别名: 4-hydroxy-3-methoxy-4-[3-[[(2R,3S,6S)-6-methoxy-2-[tri(propan-2-yl)silyloxymethyl]-3,6-dihydro-2H-pyran-3-yl]oxy]prop-1-ynyl]-2-phenylcyclobut-2-en-1-one
• CAS: 171973-10-7
• 化学式: C₃₀H₄₂O₇Si
• 分子量: 542.745
• InChiKey: XFHXWJJPMGZBEW-FUFUOGOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dideoxy-4-O-<3-(1-hydroxy-2-methoxy-3-phenyl-4-oxo-2-cyclobuten-1-yl)-2-propynyl>-6-O--α-D-erythro-hex-2-enopyranoside 以 甲苯 为溶剂， 反应 0.67h， 以63%的产率得到<2S-(2α,4β,4aβ,10bβ)>-1,2,4,4a,6,10b-hexahydro-2,9-dimethoxy-8-phenyl-4-<oxy>pyrano<3,4-c><2>benzopyran-7,10-dione
  参考文献：
  名称：

  Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Enantiomerically Pure Pyranoquinones from 4-(4-Oxo-1,6-enynyl)-4-hydroxycyclobutenones and 4-(4-Oxo-1,6-dialkynyl)-4-hydroxycyclobutenones

  摘要：

  Thermolysis of 4-(4-oxo-1,6-enynyl)-4-hydroxycyclobutenones 23 in refluxing toluene provides an enantiospecific synthesis of pyranoquinones 27. The 4-methoxy analog 32 was shown to give a quinone methide 35 and ultimately the trimer 36.

  DOI：

  10.1021/jo00125a037
• 作为产物：
  描述：

  methyl 2,3-dideoxy-4,6-dihydroxy-α-D-erythro-hex-2-enopyranoside 在 咪唑 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 3.5h， 生成 methyl 2,3-dideoxy-4-O-<3-(1-hydroxy-2-methoxy-3-phenyl-4-oxo-2-cyclobuten-1-yl)-2-propynyl>-6-O--α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Enantiomerically Pure Pyranoquinones from 4-(4-Oxo-1,6-enynyl)-4-hydroxycyclobutenones and 4-(4-Oxo-1,6-dialkynyl)-4-hydroxycyclobutenones

  摘要：

  Thermolysis of 4-(4-oxo-1,6-enynyl)-4-hydroxycyclobutenones 23 in refluxing toluene provides an enantiospecific synthesis of pyranoquinones 27. The 4-methoxy analog 32 was shown to give a quinone methide 35 and ultimately the trimer 36.

  DOI：

  10.1021/jo00125a037

文献信息

• Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Enantiomerically Pure Pyranoquinones from 4-(4-Oxo-1,6-enynyl)-4-hydroxycyclobutenones and 4-(4-Oxo-1,6-dialkynyl)-4-hydroxycyclobutenones
  作者：Yifeng Xiong、Haiji Xia、Harold W. Moore

  DOI：10.1021/jo00125a037

  日期：1995.10

  Thermolysis of 4-(4-oxo-1,6-enynyl)-4-hydroxycyclobutenones 23 in refluxing toluene provides an enantiospecific synthesis of pyranoquinones 27. The 4-methoxy analog 32 was shown to give a quinone methide 35 and ultimately the trimer 36.