1-(2-Oxa-3-aza-bicyclo[2.2.1]hept-5-en-3-yl)-2-phenyl-ethanone

• 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: 1-(2-Oxa-3-aza-bicyclo[2.2.1]hept-5-en-3-yl)-2-phenyl-ethanone
• 英文别名: 1-(2-Oxa-3-azabicyclo[2.2.1]hept-5-en-3-yl)-2-phenylethanone
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: PXAWMDJHLRWUEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-Oxa-3-aza-bicyclo[2.2.1]hept-5-en-3-yl)-2-phenyl-ethanone 在 甲醇 、 二氯二茂钛 、 锌 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 0.8h， 以79%的产率得到(+/-)-cis-N-(4-hydroxycyclopent-2-enyl)-2-phenylacetamide
  参考文献：
  名称：

  Titanocene(III) Chloride-Mediated Reductions of Oxazines, Hydroxamic Acids, and N-Hydroxy Carbamates

  摘要：

  Titanocene(III) chloride (Cp2TiCl), generated in situ, reduces N-O bonds of various substrates in good to excellent yields (72-95%). Reactions may be performed with stoichiometric Cp2TiCl or with catalytic Cp2TiCl.

  DOI：

  10.1021/jo802184y

文献信息

• Stereo- and Regioselectivity of Pd⁰/InI-Mediated Allylic Additions to Aldehydes and Ketones. <i>In Situ</i> Generation of Allylindium(III) Intermediates from <i>N</i>-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes
  作者：Wenlin Lee、Kyung-Hee Kim、Matthew D. Surman、Marvin J. Miller

  DOI：10.1021/jo026488z

  日期：2003.1.1

  and regiochemistry of their additions to aldehydes and ketones were investigated. Solvent, catalyst, and ionic effects were examined for the reaction of N-acetyl cycloadduct (11) and benzyloxyacetaldehyde (10). The solvent mixture of THF/H(2)O with Pd(OAc)(2).PPh(3) catalysis was found to be optimal. The addition of N-acetyl cycloadduct to aliphatic aldehydes afforded products in good yields and high

  酰基亚硝基Diels-Alder环加合物（11、37和45）和环戊烯基乙酸酯（8和9）衍生自钯（0）催化剂和碘化铟（I），以及立体异构体研究了它们向醛和酮中的添加的区域化学。检查了N-乙酰基环加合物（11）和苄氧基乙醛（10）反应的溶剂，催化剂和离子效应。发现THF / H（2）O与Pd（OAc）（2）.PPh（3）催化的混合溶剂是最佳的。将N-乙酰基环加合物添加到脂族醛中，以高收率和高区域和立体选择性提供产物，其中顺式1，4-异构体占产物的90-95％。与N-Boc（37a）和N-甲基氨基甲酸酯（37b）环加合物的反应也主要产生顺式1,4-产物。同样的区域选择性和立体选择性也适用于4-乙酰氧基-1-（N-羟基苯乙酰胺基）环戊烯的反应（8）。然而，4-乙酰氧基-1-苯基乙酰氨基环戊烯（9）仅提供反式-1,4-产物。描述了涉及螯合过渡态的机械推测。
• Regio- and Stereochemically Controlled Formation of Hydroxamic Acid Containing <i>a</i><i>nti</i>- or <i>s</i><i>yn</i>-1,4-Cycloalkenols from Acylnitroso-Derived Diels−Alder Adducts
  作者：Matthew D. Surman、Marvin J. Miller

  DOI：10.1021/jo010094a

  日期：2001.4.1

  Treatment of acylnitroso hetero Diels-Alder cycloadducts 2 with iron(III) or copper(II) in an alcohol solvent induces ring opening to afford predominantly monocyclic anti-1,4-hydroxamic acids 3. However, treatment of cycloadducts 2 with copper(II) in toluene reverses the stereoselectivity of the ring opening to afford syn-1,4-hydroxamic acids 4. These regio- and stereoselective processes separately

  在醇溶剂中用铁（III）或铜（II）处理酰基亚硝基杂Diels-Alder环加合物2会引起开环，从而主要提供单环抗1,4-异羟肟酸3。但是，用铜（II）处理环加合物2 ）在甲苯中逆转开环的立体选择性，得到syn-1,4-异羟肟酸4。这些区域和立体选择过程分别提供抗1,4-和syn-1,4-二取代的环戊烯，同时再生异羟肟酸从而提高了Diels-Alder环加合物的化学通用性。
• Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser’s salt: one-pot preparation of diverse carbocyclic scaffolds
  作者：Cara Cesario、Marvin J. Miller

  DOI：10.1016/j.tetlet.2010.04.007

  日期：2010.6

  A formyl equivalent was generated in situ from Eschenmoser's salt in aqueous THF and was reacted with an allylindium species. Acylnitroso-derived hetero-Diels-Alder adducts and related allyl acetates were shown to be substrates for Pd(0)/InI-mediated allylations of formaldehyde-related species to provide homoallylic alcohols. Hydroxymethyl groups were installed with regio- and diastereocontrol to provide relevant disubstituted carbocyclic scaffolds. Enantiopure anti-disubstituted cyclopentene products were prepared from a chiral allyl acetate. (C) 2010 Elsevier Ltd. All rights reserved.