5-[2-[(4-Methoxyphenoxy)methyl]phenyl]-1'-methyl-4'-(phenylmethoxymethyl)-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-2'-one | 916445-70-0

• 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-4'-(phenylmethoxymethyl)-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-2'-one
• CAS: 916445-70-0
• 化学式: C₃₈H₃₇NO₆
• 分子量: 603.715
• InChiKey: NNVQPPTXJIAOTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[2-[(4-Methoxyphenoxy)methyl]phenyl]-1'-methyl-4'-(phenylmethoxymethyl)-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-2'-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (3R,3'R)-3'-[2-[(4-methoxyphenoxy)methyl]phenyl]-1-methyl-4-(phenylmethoxymethyl)-3'-prop-2-enylspiro[indole-3,4'-oxane]-2,2'-dione 、 (3R,3'S)-3'-[2-[(4-methoxyphenoxy)methyl]phenyl]-1-methyl-4-(phenylmethoxymethyl)-3'-prop-2-enylspiro[indole-3,4'-oxane]-2,2'-dione
  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 咪唑 、 biphenyldicyclohexylphosphine 、 四丁基氟化铵 、 三甲基铝 、 sodium acetate 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 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， 85.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 5-[2-[(4-Methoxyphenoxy)methyl]phenyl]-1'-methyl-4'-(phenylmethoxymethyl)-6-prop-2-enoxyspiro[2,3-dihydropyran-4,3'-indole]-2'-one
  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

文献信息

• Synthetic Studies on Perophoramidine and the Communesins:  Construction of the Vicinal Quaternary Stereocenters
  作者：Jae Hong Seo、Gerald D. Artman、Steven M. Weinreb

  DOI：10.1021/jo061660a

  日期：2006.11.1

  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.