5-(di-tert-butyl-fluoro-silanyloxy)-4-hydroxymethyl-hexahydro-1,3-dioxacyclopropa[cd]inden-2-one | 361456-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-(di-tert-butyl-fluoro-silanyloxy)-4-hydroxymethyl-hexahydro-1,3-dioxacyclopropa[cd]inden-2-one
• CAS: 361456-17-9
• 化学式: C₁₆H₂₇FO₅Si
• 分子量: 346.471
• InChiKey: HCXCTGXBYGOFME-OJEZURLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(di-tert-butyl-fluoro-silanyloxy)-4-hydroxymethyl-hexahydro-1,3-dioxacyclopropa[cd]inden-2-one 在 吡啶 、 铜 、 氟化氢吡啶 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 50.33h， 生成 (2R,3S)-2-((R)-1-Hydroxy-allyl)-5-oxo-tetrahydro-furan-3-carbaldehyde
  参考文献：
  名称：

  Intramolecular Cyclopropanation of Glycals:  Studies toward the Synthesis of Canadensolide, Sporothriolide, and Xylobovide

  摘要：

  [GRAPHICS]The first examples of copper-catalyzed intramolecular cyclopropanations of glycal-derived diazoacetates are reported. The new cyclopropanes are converted Into advanced intermediates for the synthesis of bislactone natural products. Synthetic highlights include the selective monodeprotection of a di-tert-butylsilylene ether and a zinc-mediated ring opening cascade reaction.

  DOI：

  10.1021/ol016239h
• 作为产物：
  描述：

  6,6-di-tert-butyl-hexahydro-1,3,5,7-tetraoxa-6-sila-benzo[g]cyclopropa[cd]inden-2-one 在 三氟化硼乙醚 、 烯丙基三甲基硅烷 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以95%的产率得到5-(di-tert-butyl-fluoro-silanyloxy)-4-hydroxymethyl-hexahydro-1,3-dioxacyclopropa[cd]inden-2-one
  参考文献：
  名称：

  Intramolecular Cyclopropanation of Glycals:  Studies toward the Synthesis of Canadensolide, Sporothriolide, and Xylobovide

  摘要：

  [GRAPHICS]The first examples of copper-catalyzed intramolecular cyclopropanations of glycal-derived diazoacetates are reported. The new cyclopropanes are converted Into advanced intermediates for the synthesis of bislactone natural products. Synthetic highlights include the selective monodeprotection of a di-tert-butylsilylene ether and a zinc-mediated ring opening cascade reaction.

  DOI：

  10.1021/ol016239h

文献信息

• Formal [3 + 2] Cycloadditions of Donor−Acceptor Cyclopropanes and Nitriles
  作者：Ming Yu、Brian L. Pagenkopf

  DOI：10.1021/ja029716f

  日期：2003.7.1

  Donor-acceptor cyclopropanes activated with Me3SiOTf cleave to reactive intermediates that can be efficiently intercepted by nitriles in a formal [3 + 2] dipolar cycloaddition reaction. Aliphatic, aromatic, and alpha,beta-unsaturated nitriles are excellent reaction partners, giving synthetically useful 2H-3,4-dihydropyrrole cycloaddition products in high yield.