(R)-3-(pent-4-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one | 1009605-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 英文名称: (R)-3-(pent-4-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (3R)-5-pent-4-enyl-3-phenyl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 1009605-77-9
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: LBUMYCVDVABLRV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(pent-4-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 在 三(二甲氨基)锍二氟三甲基硅酸 、 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 二甲基亚砜 为溶剂， 反应 96.0h， 生成 (-)-(4R,6S,9aS)-6-(acetoxymethyl)-4-phenyl-9a-(trifluoromethyl)-3,4,6,7-tetrahydropyrido[2,1-c][1,4]oxazin-1(9aH)-one
  参考文献：
  名称：

  立体选择获得氟化和非氟化季戊啶：哌酸和亚氨基糖衍生物的合成

  摘要：

  通过衍生自（R）-苯基甘氨醇的手性亚氨基内酯可以制备出氟化的和非氟化的光学纯的季哌啶。在含氟衍生物的情况下，加入（三氟甲基）三甲基硅烷（TMSCF 3），然后进行碘化和CF 3基团的迁移，可以得到α-（三氟甲基）哌酸的四个衍生物。CF 3的理论研究进行了基团重排，以帮助建立这种罕见转化的反应机理。此外，还通过合适的合成中间体的非对映选择性二羟基化开发了一条通往三氟甲基取代的亚氨基糖的途径。相反，起始底物的烷基化以及随后的交叉复分解和氮杂-Michael反应导致目标化合物的α-烷基衍生物。

  DOI：

  10.1002/chem.201102351
• 作为产物：
  描述：

  D-苯甘氨醇 、 2-氧代庚-6-烯酸乙酯 在 3 A molecular sieve 作用下， 以 various solvent(s) 为溶剂， 反应 0.75h， 以50%的产率得到(R)-3-(pent-4-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n

文献信息

• Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids
  作者：Santos Fustero、Natalia Mateu、Antonio Simón-Fuentes、José Luis Aceña

  DOI：10.1021/ol1010246

  日期：2010.7.2

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.
• An Efficient Entry to Optically Active <i>anti</i>- and <i>syn</i>-β-Amino-α-trifluoromethyl Alcohols
  作者：Santos Fustero、Laia Albert、José Luis Aceña、Juan F. Sanz-Cervera、Amparo Asensio

  DOI：10.1021/ol702947n

  日期：2008.2.1

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.
• Stereoselective Access to Fluorinated and Non-fluorinated Quaternary Piperidines: Synthesis of Pipecolic Acid and Iminosugar Derivatives
  作者：Santos Fustero、Laia Albert、Natalia Mateu、Gema Chiva、Javier Miró、Javier González、José Luis Aceña

  DOI：10.1002/chem.201102351

  日期：2012.3.19

  quaternary piperidines, both fluorinated and non‐fluorinated, has been achieved from a chiral imino lactone derived from (R)‐phenylglycinol. In the case of the fluorinated derivatives, the addition of (trifluoromethyl)trimethylsilane (TMSCF3) followed by iodoamination and migration of the CF3 group allowed access to four derivatives of α‐(trifluoromethyl)pipecolic acid. A theoretical study of the CF3‐group

  通过衍生自（R）-苯基甘氨醇的手性亚氨基内酯可以制备出氟化的和非氟化的光学纯的季哌啶。在含氟衍生物的情况下，加入（三氟甲基）三甲基硅烷（TMSCF 3），然后进行碘化和CF 3基团的迁移，可以得到α-（三氟甲基）哌酸的四个衍生物。CF 3的理论研究进行了基团重排，以帮助建立这种罕见转化的反应机理。此外，还通过合适的合成中间体的非对映选择性二羟基化开发了一条通往三氟甲基取代的亚氨基糖的途径。相反，起始底物的烷基化以及随后的交叉复分解和氮杂-Michael反应导致目标化合物的α-烷基衍生物。