4'-methoxy-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-carbaldehyde | 1353009-85-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 4'-methoxy-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-carbaldehyde
• 英文别名: 2-(4-methoxyphenyl)cyclohex-1-enecarbaldehyde；2-(4-Methoxyphenyl)cyclohexene-1-carbaldehyde；2-(4-methoxyphenyl)cyclohexene-1-carbaldehyde
• CAS: 1353009-85-4
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: OFKWODPLZBYQKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-methoxy-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-carbaldehyde 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 4-氯苯磺酸 、 4-(aminooxycarbonyl)benzonitrile 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以45%的产率得到3-methoxy-7,8,9,10-tetrahydrophenanthridine
  参考文献：
  名称：

  Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and O-Acyl Hydroxylamine

  摘要：

  A one-pot synthesis of phenanthridines and quinolines from commercially available or easily prepared aldehydes has been reported. O-(4-Cyanobenzoyl)hydroxylamine was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes catalyzed by Bronsted acid. O-Acyl oximes were then subjected to visible light photoredox catalyzed cyclization via iminyl radicals to furnish aza-arenes. A variety of phenanthridines and quinolines have been prepared assisted by Bronsted acid and photocatalyst under visible light at room temperature with satisfactory yields.

  DOI：

  10.1021/acs.orglett.5b01096
• 作为产物：
  描述：

  4-甲氧基苯硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 4'-methoxy-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-carbaldehyde
  参考文献：
  名称：

  铃木-Miyaura交叉偶联和铱催化的不对称加氢对映异构合成顺式1,2-二取代的环戊烷和环己烷

  摘要：

  通过Suzuki-Miyaura将2-溴-1-环己烯甲醛或2-羰甲氧基-1-环己烯-1-基三氟甲磺酸酯与芳基硼酸酯的交叉偶联制备了一系列1,2-二取代的环己烯衍生物。这些四取代的环状烯烃经过Ir催化的不对称氢化反应。通过使用膦基甲基恶唑啉作为配体，以这种方式以高收率获得了具有高对映选择性和非对映选择性（高达> 99％ee，> 99％ 顺式）的顺-1-甲氧基甲基-2-芳基环己烷 。Suzuki-Miyaura交叉偶合制备的类似环戊烯衍生物的不对称氢化被证明更困难，并且对映体选择性较低，最高可达88％  ee。这种交叉偶联/不对称氢化策略的合成潜力通过手性六氢芴酮的对映选择性途径得到证明。

  DOI：

  10.1002/chem.201102650

文献信息

• Ligand-Free Suzuki Cross-Coupling Reactions: Application to β-Halo-α,β-Unsaturated Aldehydes
  作者：Pranjal Gogoi、Pranjal Bezboruah、Romesh C. Boruah

  DOI：10.1002/ejoc.201300491

  日期：2013.8

  ligand-free Suzuki–Miyaura reaction of β-halo α,β-unsaturated aldehydes with boronic acids in aqueous media at room temperature is described. Under the optimized conditions, both steroidal and nonsteroidal β-halo α,β-unsaturated aldehydes reacted rapidly with the boronic acids to provide a series of aryl-substituted derivatives in excellent yields. Moreover, the protocol was extended to the direct one-pot

  描述了 β-卤代 α,β-不饱和醛与硼酸在室温下在水性介质中的一种简便、高效、无配体的 Suzuki-Miyaura 反应。在优化的条件下，甾体和非甾体 β-卤代 α,β-不饱和醛均与硼酸快速反应，以优异的产率提供了一系列芳基取代的衍生物。此外，该协议还扩展到在微波辐射下通过 Suzuki-Miyaura 交叉偶联/醇醛缩合级联反应直接一锅法合成多环芳烃。
• Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and <i>O</i>-Acyl Hydroxylamine
  作者：Xiao-De An、Shouyun Yu

  DOI：10.1021/acs.orglett.5b01096

  日期：2015.6.5

  A one-pot synthesis of phenanthridines and quinolines from commercially available or easily prepared aldehydes has been reported. O-(4-Cyanobenzoyl)hydroxylamine was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes catalyzed by Bronsted acid. O-Acyl oximes were then subjected to visible light photoredox catalyzed cyclization via iminyl radicals to furnish aza-arenes. A variety of phenanthridines and quinolines have been prepared assisted by Bronsted acid and photocatalyst under visible light at room temperature with satisfactory yields.
• Enantioselective Synthesis of cis-1,2-Disubstituted Cyclopentanes and Cyclohexanes by Suzuki-Miyaura Cross-Coupling and Iridium-Catalyzed Asymmetric Hydrogenation
  作者：Andreas Schumacher、Marcus G. Schrems、Andreas Pfaltz

  DOI：10.1002/chem.201102650

  日期：2011.11.25

  using phosphinomethyloxazolines as ligands. Asymmetric hydrogenation of analogous cyclopentene derivatives, prepared by Suzuki–Miyaura cross‐coupling, proved to be more difficult and proceeded with lower enantioselectivities of up to 88 % ee. The synthetic potential of this cross‐coupling/asymmetric‐hydrogenation strategy was demonstrated by an enantioselective route to chiral hexahydrofluorenones.

  通过Suzuki-Miyaura将2-溴-1-环己烯甲醛或2-羰甲氧基-1-环己烯-1-基三氟甲磺酸酯与芳基硼酸酯的交叉偶联制备了一系列1,2-二取代的环己烯衍生物。这些四取代的环状烯烃经过Ir催化的不对称氢化反应。通过使用膦基甲基恶唑啉作为配体，以这种方式以高收率获得了具有高对映选择性和非对映选择性（高达> 99％ee，> 99％ 顺式）的顺-1-甲氧基甲基-2-芳基环己烷 。Suzuki-Miyaura交叉偶合制备的类似环戊烯衍生物的不对称氢化被证明更困难，并且对映体选择性较低，最高可达88％  ee。这种交叉偶联/不对称氢化策略的合成潜力通过手性六氢芴酮的对映选择性途径得到证明。