tert-butyl N-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-5-[dimethyl(oxo)-lambda6-sulfanylidene]-4-oxopentyl]carbamate | 1179348-70-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl N-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-5-[dimethyl(oxo)-lambda6-sulfanylidene]-4-oxopentyl]carbamate
• 英文别名: tert-butyl N-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-5-[dimethyl(oxo)-λ6-sulfanylidene]-4-oxopentyl]carbamate
• CAS: 1179348-70-9
• 化学式: C₁₈H₃₇NO₅SSi
• 分子量: 407.647
• InChiKey: PIVXXHCZFPGOKG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-5-[dimethyl(oxo)-lambda6-sulfanylidene]-4-oxopentyl]carbamate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以90%的产率得到tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-5-oxopiperidine-1-carboxylate
  参考文献：
  名称：

  Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides

  摘要：

  The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

  DOI：

  10.1021/ol901298p
• 作为产物：
  描述：

  三甲基氯化亚砜 、 tert-butyl (R)-4-((tert-butyldimethylsilyl)oxy)-2-oxopyrrolidine-1-carboxylate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以54%的产率得到tert-butyl N-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-5-[dimethyl(oxo)-lambda6-sulfanylidene]-4-oxopentyl]carbamate
  参考文献：
  名称：

  Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides

  摘要：

  The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

  DOI：

  10.1021/ol901298p

文献信息

• Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides
  作者：Ian K. Mangion、Ikenna K. Nwamba、Michael Shevlin、Mark A. Huffman

  DOI：10.1021/ol901298p

  日期：2009.8.20

  The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.