(3R)-3-phenyl-3,4-dihydroisoquinoline | 842137-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: (3R)-3-phenyl-3,4-dihydroisoquinoline
• 英文别名: (R)-3-phenyl-3,4-dihydroisoquinoline；(R)-3,4-dihydro-3-phenylisoquinoline
• CAS: 842137-95-5
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: DJNIVCWGPZMVSO-OAHLLOKOSA-N

物化性质

• 沸点：
  342.3±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-苯基萘-2-醇 、 (3R)-3-phenyl-3,4-dihydroisoquinoline 以 水 为溶剂， 以48%的产率得到3-phenyl-1-((1S,3R)-3-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)naphthalen-2-ol
  参考文献：
  名称：

  Synthesis of Chiral 1,3-Disubstituted Tetrahydroisoquinolines and Their Use in the Asymmetric Addition of Diethylzinc to Aldehydes

  摘要：

  The effects of modifications on three sites of 1-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-naphthalen-2-ol (THIQNOL) chiral ligands the asymmetric diethylzinc additions were examined. The studies showed that modifications at the nitrogen only reduce the efficiency of these types of ligands, whereas modifications at the 3-position of the 1,2,3,4-tetrahydroisoquinoline ring and the 3-position of the naphthol ring can lead to chiral ligands which provide better enantioselectivities. In general, the use of a simple phenyl group on the 1,2,3,4-tetrahydroisoquinoline ring and either a phenyl or methoxyphenyl on the naphthol ring generates more effective chiral ligands for the asymmetric addition of diethylzinc to aldehydes.

  DOI：

  10.3987/com-09-s(s)123
• 作为产物：
  描述：

  N,N-二乙基-2-甲基苯甲酰胺 在 氨 、 lithium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 生成 (3R)-3-phenyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  通过 1,2-加成/闭环不对称合成 3-取代的二氢-2H-异喹啉-1-酮、二氢和四氢异喹啉

  摘要：

  描述了 3-取代二氢-2H-异喹啉-1-酮、二氢和四氢异喹啉的不对称合成。关键操作是串联 1,2-加成/闭环序列，使用锂化邻甲苯酰胺和醛 SAMP-或 RAMP-腙作为底物，然后进行 NN 键断裂以去除辅助剂。达到中等至良好的产率和高对映体过量（ee = 85-99%）。

  DOI：

  10.1055/s-2004-834861

文献信息

• LIGANDS, THEIR PREPARATION AND USES THEREOF IN ASYMMETRIC REACTIONS
  申请人：Li Chao-Jun

  公开号：US20090247757A1

  公开（公告）日：2009-10-01

  Novel chemical agents are described herein. More a ligand of general Formula I: wherein R 1 , R 2 , R 3 and R 4 , are independently selected from the group consisting of hydrogen, halogen, hydroxy, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 alkoxy, C 1 -C 10 alkylthio, C(O)R 5 , C(O)OR 5 , C(O)NHR 5 , Si(R 5 ) 3 , benzyl and aryl; X is selected from the group consisting of Cl, Br, I, OR 6 , O-Prot, OPR 6 , P(R 6 ) 2 , NHR 6 , N(R 6 ) 2 , NHCSNHR 6 , NHCONHR 6 and SR 6 ; and R 5 and R 6 are independently selected from the group consisting of hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 1-10 alkoxy, phenyl, and aryl. These ligands are useful in asymmetric reactions as well as in asymmetric synthesis of molecules of biological interest.

  本文描述了一种新型化学试剂。更多地是一种一般化学式I的配体：其中R1、R2、R3和R4分别选自氢、卤素、羟基、C1-C10烷基、C2-C10烯基、C2-C10炔基、C1-C10烷氧基、C1-C10烷硫基、C(O)R5、C(O)OR5、C(O)NHR5、Si(R5)3、苄基和芳基；X选自Cl、Br、I、OR6、O-Prot、OPR6、P(R6)2、NHR6、N(R6)2、NHCSNHR6、NHCONHR6和SR6；R5和R6分别选自氢、C1-10烷基、C2-10烯基、C2-10炔基、C1-10烷氧基、苯基和芳基。这些配体在不对称反应以及生物感兴趣分子的不对称合成中是有用的。
• Ligands, their preparation and uses thereof in asymmetric reactions
  申请人：——

  公开号：US08183378B2

  公开（公告）日：2012-05-22

  Novel chemical agents are described herein. More a ligand of general Formula I: wherein R1, R2, R3 and R4, are independently selected from the group consisting of hydrogen, halogen, hydroxy, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy, C1-C10 alkylthio, C(O)R5, C(O)OR5, C(O)NHR5, Si(R5)3, benzyl and aryl; X is selected from the group consisting of Cl, Br, I, OR6, O-Prot, OPR6, P(R6)2, NHR6, N(R6)2, NHCSNHR6, NHCONHR6 and SR6; and R5 and R6 are independently selected from the group consisting of hydrogen, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C1-10 alkoxy, phenyl, and aryl. These ligands are useful in asymmetric reactions as well as in asymmetric synthesis of molecules of biological interest.

  本文介绍了一些新型的化学试剂。其中包括一种普遍式I的配体，其中R1、R2、R3和R4独立地选择自氢、卤素、羟基、C1-C10烷基、C2-C10烯基、C2-C10炔基、C1-C10烷氧基、C1-C10烷硫基、C（O）R5、C（O）OR5、C（O）NHR5、Si（R5）3、苄基和芳基；X选择自Cl、Br、I、OR6、O-Prot、OPR6、P（R6）2、NHR6、N（R6）2、NHCSNHR6、NHCONHR6和SR6；R5和R6独立地选择自氢、C1-10烷基、C2-10烯基、C2-10炔基、C1-10烷氧基、苯基和芳基。这些配体在不对称反应以及生物分子的不对称合成中是有用的。
• Synthesis of a new type of chiral N,P- and N,O-ligands
  作者：Jianqing Feng、Sarim Dastgir、Chao-Jun Li

  DOI：10.1016/j.tetlet.2007.11.126

  日期：2008.1

  Novel chiral ligands of dihydro-QUINAP (FLiNAP) and dihydro-QUINOL (FLiNOL) have been synthesized in optically pure forms. (c) 2007 Elsevier Ltd. All rights reserved.
• US8183378B2
  申请人：——

  公开号：US8183378B2

  公开（公告）日：2012-05-22
• Asymmetric Synthesis of 3-Substituted Dihydro-2<i>H</i>-isoquinolin-1-ones, Dihydro- and Tetrahydroisoquinolines via 1,2-Addition/Ring Closure
  作者：Dieter Enders、Volker Braig、Marine Boudou、Gerhard Raabe

  DOI：10.1055/s-2004-834861

  日期：——

  The asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines is described. The key operation is a tandem 1,2-addition/ring closure sequence employing lithiated ortho-toluamides and aldehyde SAMP-or RAMP-hydrazones as substrates, followed by N-N bond cleavage to remove the auxiliary. Moderate to good yields and high enantiomeric excesses (ee = 85-99%)

  描述了 3-取代二氢-2H-异喹啉-1-酮、二氢和四氢异喹啉的不对称合成。关键操作是串联 1,2-加成/闭环序列，使用锂化邻甲苯酰胺和醛 SAMP-或 RAMP-腙作为底物，然后进行 NN 键断裂以去除辅助剂。达到中等至良好的产率和高对映体过量（ee = 85-99%）。