(1S,3R,5S,6S,7R)-6-[tert-butyl(dimethyl)silyl]oxy-8-[(4-methoxyphenyl)methyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one | 627873-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,3R,5S,6S,7R)-6-[tert-butyl(dimethyl)silyl]oxy-8-[(4-methoxyphenyl)methyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one
• CAS: 627873-29-4
• 化学式: C₂₀H₂₉NO₄Si
• 分子量: 375.54
• InChiKey: QPCGPTVUBWLCIT-YKEMRQTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3R,5S,6S,7R)-6-[tert-butyl(dimethyl)silyl]oxy-8-[(4-methoxyphenyl)methyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one 在 氢氟酸 、 氢溴酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 (+/-)-bromoxone
  参考文献：
  名称：

  氮丙啶为保护和引导基团。（+）-溴酮的立体选择性合成。

  摘要：

  [反应：见正文]证实了氮丙啶基团对相邻双键环氧化的指导能力。氮丙啶基团还用于有效保护环烯酮系统中的双键，以短时间合成标题化合物。

  DOI：

  10.1021/ol035576i
• 作为产物：
  描述：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 在 4-二甲氨基吡啶 、 1,10-菲罗啉 、 双氧水 、 碘 、 苄基三甲基氢氧化铵 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 生成 (1S,3R,5S,6S,7R)-6-[tert-butyl(dimethyl)silyl]oxy-8-[(4-methoxyphenyl)methyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octan-2-one
  参考文献：
  名称：

  Use of Aziridines for the Stereocontrolled Synthesis of (−)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214

  摘要：

  Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.

  DOI：

  10.1021/jo402535j

文献信息

• Use of Aziridines for the Stereocontrolled Synthesis of (−)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214
  作者：Christopher D. Maycock、Paula Rodrigues、M. Rita Ventura

  DOI：10.1021/jo402535j

  日期：2014.3.7

  Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.
• Aziridines as a Protecting and Directing Group. Stereoselective Synthesis of (+)-Bromoxone
  作者：M. Teresa Barros、Pedro M. Matias、Christopher D. Maycock、M. Rita Ventura

  DOI：10.1021/ol035576i

  日期：2003.11.1

  [reaction: see text] The directing ability of an aziridine group for the epoxidation of adjacent double bonds is demonstrated. The aziridine group is also used to effectively protect a double bond in a cycloenone system for a short synthesis of the title compound.

  [反应：见正文]证实了氮丙啶基团对相邻双键环氧化的指导能力。氮丙啶基团还用于有效保护环烯酮系统中的双键，以短时间合成标题化合物。