(3S,4S)-4-(1-n-pentylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone | 1044260-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4S)-4-(1-n-pentylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
• CAS: 1044260-04-9
• 化学式: C₁₉H₃₅NO₂Si
• 分子量: 337.578
• InChiKey: GVPAWCHLAUGWHR-DJIMGWMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-(1-n-pentylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone 、 p-tolyl isoselenocyanate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.33h， 以96%的产率得到
  参考文献：
  名称：

  Synthesis of 3-Selena-1-dethiacephems and Selenazepines via Iodocyclization

  摘要：

  A convenient approach to synthesize novel selenium-beta-lactams, 3-selena-1-dethiacephems and selenazepines, was accomplished via the regioselective iodocyclization reaction. The substituent of allenyl moieties dramatically influenced the regiochemical outcome in the iodocyclization of allene-selenourea derivatives.

  DOI：

  10.1021/ol801010y
• 作为产物：
  描述：

  1-溴-2辛炔 、 4-乙酰氧基氮杂环丁酮 在 indium 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以94%的产率得到(3S,4S)-4-(1-n-pentylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
  参考文献：
  名称：

  Synthesis of 3-Selena-1-dethiacephems and Selenazepines via Iodocyclization

  摘要：

  A convenient approach to synthesize novel selenium-beta-lactams, 3-selena-1-dethiacephems and selenazepines, was accomplished via the regioselective iodocyclization reaction. The substituent of allenyl moieties dramatically influenced the regiochemical outcome in the iodocyclization of allene-selenourea derivatives.

  DOI：

  10.1021/ol801010y

文献信息

• First iodocyclization reaction of allene–thioureas: an efficient approach to bicyclic β-lactams
  作者：Dinesh R. Garud、Amol R. Jadhav、Santosh V. Lahore、Nilesh M. Kahar、Rohini R. Joshi、Ramesh A. Joshi、Mamoru Koketsu

  DOI：10.1016/j.tetlet.2014.09.004

  日期：2014.10

  The regioselective iodocyclization reaction of allene-thioureas is described, for the first time, for the synthesis of bicyclic beta-lactams. The substitution at the allenyl part heavily influenced the iodocyclization reaction. The iodocyclization reaction of the unsubstituted allene-thioureas afforded six-membered 3-thia-1-dethiacephems whereas, the substituted allene-thiourea afforded seven-membered thiazepines along with five-membered isopenams. (C) 2014 Elsevier Ltd. All rights reserved.