2-{1-[2-(tert-butyldiphenylsilyloxy)propyl]-5-hexenyl}-1H-isoindole-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{1-[2-(tert-butyldiphenylsilyloxy)propyl]-5-hexenyl}-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[(2R,4S)-2-[tert-butyl(diphenyl)silyl]oxynon-8-en-4-yl]isoindole-1,3-dione
• 化学式: C₃₃H₃₉NO₃Si
• 分子量: 525.763
• InChiKey: XJFLDABTAYDEPQ-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-{1-[2-(tert-butyldiphenylsilyloxy)propyl]-5-hexenyl}-1H-isoindole-1,3(2H)-dione 在 sodium tetrahydroborate 作用下， 以 水 、 异丙醇 为溶剂， 以100%的产率得到(2S,4S)-2-(tert-butyldiphenylsilyloxy)-8-nonen-4-amine
  参考文献：
  名称：

  A Diastereoselective Intramolecular Hydroamination Approach to the Syntheses of (+)-, (±)-, and (−)-Pinidinol

  摘要：

  A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)(2) converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100:1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.

  DOI：

  10.1021/jo015603n
• 作为产物：
  描述：

  5-碘-1-戊烯 在 咪唑 、 sodium tetrahydroborate 、 正丁基锂 、 无水碳酸镉 、 水 、 三苯基膦 、 mercury dichloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-{1-[2-(tert-butyldiphenylsilyloxy)propyl]-5-hexenyl}-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  A Diastereoselective Intramolecular Hydroamination Approach to the Syntheses of (+)-, (±)-, and (−)-Pinidinol

  摘要：

  A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)(2) converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100:1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.

  DOI：

  10.1021/jo015603n

文献信息

• A Diastereoselective Intramolecular Hydroamination Approach to the Syntheses of (+)-, (±)-, and (−)-Pinidinol
  作者：Gary A. Molander、Eric D. Dowdy、Shawn K. Pack

  DOI：10.1021/jo015603n

  日期：2001.6.1

  A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)(2) converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100:1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.