(R)-4-oxo-2-phenyl-piperidine-1-carboxylic acid benzyl ester | 335266-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-4-oxo-2-phenyl-piperidine-1-carboxylic acid benzyl ester
• 英文别名: (R)-benzyl 4-oxo-2-phenylpiperidine-1-carboxylate；(+)-(R)-N-carbobenzyloxy-2-phenyl-4-piperidone；benzyl 4-oxo-2-phenylpiperidine-1-carboxylate；(R)-4-N-carbobenzyloxy-2-phenyl-4-piperidone；benzyl (2R)-4-oxo-2-phenylpiperidine-1-carboxylate
• CAS: 335266-05-2
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: DLEUYEPFFNLJCI-GOSISDBHSA-N

物化性质

• 沸点：
  481.6±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  4-甲氧基吡啶 在 三异丙氧基硼氢化钾 、 1,1-bis(3,5-dimethylphenyl)-N,N-bis((S)-1-(naphthalen-2-yl)ethyl)phosphinamine 、 三甲基铝 、 copper(II) β-naphthoate 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 正戊烷 为溶剂， 反应 15.0h， 生成 (R)-4-oxo-2-phenyl-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Copper-Catalyzed Asymmetric 1,4-Addition of Alkenyl Alanes to N-Substituted-2-3-dehydro-4-piperidones

  摘要：

  Readily available vinyl alanes are used in the Cu-catalyzed asymmetric conjugate addition reaction to N-substituted-2-3-dehydro-4-piperidones. The enhanced reactivity of recently developed and easily prepared phosphine amine ligands in combination with inexpensive Cu(II)naphtenate (CuNp) allows the introduction of a great variety of alkenyl, alkyl, and aryl aluminums in high enantioselectivity.

  DOI：

  10.1021/ol3004436

文献信息

• A New Entry of Nucleophiles in Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions:  Addition of Organozinc Reagents for the Synthesis of 2-Aryl-4-piperidones
  作者：Ryo Shintani、Norihito Tokunaga、Hidenori Doi、Tamio Hayashi

  DOI：10.1021/ja048825m

  日期：2004.5.1

  A rhodium-catalyzed asymmetric 1,4-addition reaction has been applied to the synthesis of 2-aryl-4-piperidones. While other conventional nucleophiles fail, organozinc reagents have been successfully utilized for the construction of these useful compounds in very good yield and enantiomeric excess.

  铑催化的不对称 1,4-加成反应已用于合成 2-芳基-4-哌啶酮。虽然其他常规亲核试剂失败，但有机锌试剂已成功用于构建这些有用的化合物，收率非常好，对映体过量。
• Enantioselective palladium-catalysed conjugate addition of arylsiloxanes
  作者：Francesca Gini、Bart Hessen、Ben L. Feringa、Adriaan J. Minnaard

  DOI：10.1039/b616969d

  日期：——

  The complex formed from Pd(CH3CN)4(BF4)2 and (R,R)-MeDUPHOS is a highly enantioselective catalyst for the asymmetric conjugate addition of aryltriethylsiloxanes to a variety of unsaturated ketones, lactones and lactams.

  由Pd(CH3CN)4(BF4)2和(R,R)-MeDUPHOS形成的络合物是一种高度对映选择性的催化剂，可用于不对称共轭加成反应，将芳基三乙硅氧烷加成到多种不饱和的酮、内酯和内酰胺中。
• Asymmetric 1,4-Addition of Arylboronic Acids to 2,3-Dihydro-4-pyridones Catalyzed by Axially Chiral NHC−Pd(II) Complexes
  作者：Qin Xu、Rui Zhang、Tao Zhang、Min Shi

  DOI：10.1021/jo1006224

  日期：2010.6.4

  Axially chiral cis-chelated bidentate bis(N-heterocyclic carbene)−palladium(II) complexes are effective catalysts for the asymmetric conjugate addition of arylboronic acids to 2,3-dihydro-4-pyridones, producing the synthetically and biologically important 2-aryl-4-piperidones in moderate-to-high yields (up to 96%) along with excellent enantioselectivities (up to >99.5% ee) in most cases under mild

  轴向手性顺式螯合双齿双（N-杂环卡宾）-钯（II）配合物是将芳基硼酸不对称共轭加成到2,3-二氢-4-吡啶酮中的有效催化剂，产生了合成上和生物学上重要的2-芳基在大多数情况下，在温和条件下，中至高产率（高达96％）的-4-哌啶酮以及出色的对映选择性（高达> 99.5％ee）。
• Palladium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids
  作者：Francesca Gini、Bart Hessen、Adriaan J. Minnaard

  DOI：10.1021/ol052222d

  日期：2005.11.1

  [reaction: see text] The first asymmetric palladium-catalyzed conjugate addition of arylboronic acids to alpha,beta-unsaturated aldehydes, ketones, and esters is described. For cyclic substrates, excellent chemo-, regio-, and enantioselectivities are achieved when a Pd(O2CCF3)2/DuPHOS catalyst is applied.

  [反应：见正文]描述了芳基硼酸向α，β-不饱和醛，酮和酯的第一次不对称钯催化的共轭加成。对于环状底物，当使用Pd（O2CCF3）2 / DuPHOS催化剂时，可获得出色的化学选择性，区域选择性和对映选择性。
• Rhodium-Catalyzed Enantioselective Conjugate Addition of Sodium Tetraarylborates to 2,3-Dihydro-4-pyridones and 4-Quinolones by Using (R,R)-1,2-Bis(tert-butylsulfinyl)benzene as a Ligand
  作者：Xiangyang Zhang、Jun Chen、Fuzhong Han、Linfeng Cun、Jian Liao

  DOI：10.1002/ejoc.201001613

  日期：2011.3

  (R,R)-1,2-Bis(tert-butylsulfinyl)benzene as an efficient and simple ligand can be applied in the rhodium-catalyzed asymmetric 1,4-addition of sodium tetraarylborate reagents to N-substituted 2,3-dihydro-4-pyridones and 4-quinolones. The reactions proceeded smoothly to provide the corresponding adducts in good yields (up to 92%) and excellent enantioselectivities (up to 99% ee) under mild conditions

  (R,R)-1,2-双(叔丁基亚磺酰基)苯作为一种高效且简单的配体可用于铑催化的四芳基硼酸钠试剂与N-取代的2,3-二氢的不对称1,4-加成反应-4-吡啶酮和4-喹诺酮。在温和的条件下，反应顺利进行，以良好的产率（高达 92%）和优异的对映选择性（高达 99% ee）提供相应的加合物。