[5-[2-[(4-methoxyphenoxy)methyl]phenyl]-1'-methyl-2'-oxo-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-4'-yl] N,N-dimethylcarbamate | 916446-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [5-[2-[(4-methoxyphenoxy)methyl]phenyl]-1'-methyl-2'-oxo-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-4'-yl] N,N-dimethylcarbamate
• CAS: 916446-12-3
• 化学式: C₃₃H₃₄N₂O₇
• 分子量: 570.642
• InChiKey: DCHXIEHDNULKTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [5-[2-[(4-methoxyphenoxy)methyl]phenyl]-1'-methyl-2'-oxo-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-4'-yl] N,N-dimethylcarbamate 以 甲苯 为溶剂， 生成 [(3R,3'R)-3'-[2-[(4-methoxyphenoxy)methyl]phenyl]-1-methyl-2,2'-dioxo-3'-prop-2-enylspiro[indole-3,4'-oxane]-4-yl] N,N-dimethylcarbamate 、
  参考文献：
  名称：

  Synthetic Studies on Perophoramidine and the Communesins:  Construction of the Vicinal Quaternary Stereocenters

  摘要：

  An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.

  DOI：

  10.1021/jo061660a
• 作为产物：
  描述：

  1,3-二氢异苯并呋喃-1-醇 在 palladium diacetate 盐酸 、 三甲基铝 、 sodium acetate 、 sodium hydride 、 N,N-二异丙基乙胺 、 三苯基膦 、 三(邻甲基苯基)磷 、 sodium iodide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 [5-[2-[(4-methoxyphenoxy)methyl]phenyl]-1'-methyl-2'-oxo-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-4'-yl] N,N-dimethylcarbamate
  参考文献：
  名称：

  Synthetic Studies on Perophoramidine and the Communesins:  Construction of the Vicinal Quaternary Stereocenters

  摘要：

  An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.

  DOI：

  10.1021/jo061660a