1,3-dihydro-α,β-diphenyl-2H-isoindole-2-ethanamine | 951322-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,3-dihydro-α,β-diphenyl-2H-isoindole-2-ethanamine
• 英文别名: (1R,2R)-1-amino-2-(2,3-dihydro-1H-isoindole-2-yl)-1,2-diphenylethane；(1R,2R)-2-(isoindolin-2-yl)-1,2-diphenylethan-1-amine；(1R,2R)-2-(isoindolin-2-yl)-1,2-diphenylethanamine；(1R,2R)-2-(1,3-dihydroisoindol-2-yl)-1,2-diphenylethanamine
• CAS: 951322-70-6
• 化学式: C₂₂H₂₂N₂
• 分子量: 314.43
• InChiKey: DQHHKQLDUGQQLC-FGZHOGPDSA-N

物化性质

• 沸点：
  433.5±40.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dihydro-α,β-diphenyl-2H-isoindole-2-ethanamine 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 {N-[trans-2-(isoindolin-2-yl)-1,2-diphenylethyl]-[3,5-bis(tertbutyl)salicylaldiminate]}NiIICl
  参考文献：
  名称：

  trans-1,2-Diphenylethylene Linked Isoindoline-Salicylaldiminato Nickel(II) 卤化物配合物：合成、结构、脱氢和对烯烃均聚的催化活性

  摘要：

  三齿配体 4-R1-6-R2-2-{[trans-2-(isoindolin-2-yl)-1,2-diphenylethylimino]methyl} 苯酚 [R1 = R2 = H, H(La); R1 = R2 = 叔丁基，H(Lb)；R1=Ph，R2=H，H(Lc)]，其中取代的水杨醛亚胺部分和异二氢吲哚通过反式-1,2-二苯基亚乙基部分连接。这些三齿配体 H(La)–H(Lc) 在室温下在四氢呋喃 (THF) 中被 NaH 去质子化，然后用 1 当量处理。[(PPh3)2NiX2] (X = Cl, Br, I) 在室温下得到所需的镍配合物 [(L)NiX] (X = Cl, L = La, 1; X = Cl, L = Lb, 2 ; X = Cl, L = Lc, 3; X = Br, L = Lb, 4; X = I, L = Lb, 5) 中等产量。2 和 4 的结构通过固态单晶

  DOI：

  10.1002/ejic.201201331
• 作为产物：
  描述：

  1R,2R-N-DAB-二苯基乙二胺 在 C.I.酸性橙108 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 1,3-dihydro-α,β-diphenyl-2H-isoindole-2-ethanamine
  参考文献：
  名称：

  实际的不对称亨利反应，由手性二胺-Cu（OAc）2配合物催化。

  摘要：

  由（R，R）-1，2-二苯基乙二胺，（S）-2，2′-二溴甲基-1，1′-联萘和邻二甲苯基二溴化物设计合成手性二胺配体3。所得的3-Cu（OAc）2络合物是亨利反应的高效催化剂，使各种硝基醛的ee均超过90％（最高> 99％）。该反应在室温下在正丙醇中进行，亨利加合物的产率高，对映体过量极好。这些特性在实际使用的催化剂中是理想的。

  DOI：

  10.1021/ol7014362

文献信息

• Catalytic Asymmetric Iodocyclization of<i>N-</i>Tosyl Alkenamides using Aminoiminophenoxy Copper Carboxylate: A Concise Synthesis of Chiral 8-Oxa-6-Azabicyclo[3.2.1]octanes
  作者：Takayoshi Arai、Ohji Watanabe、Shinnosuke Yabe、Masahiro Yamanaka

  DOI：10.1002/anie.201505748

  日期：2015.10.19

  A newly developed aminoiminophenoxy copper carboxylate (L7‐Cu‐OAc)‐catalyzed asymmetric iodocyclization of N‐Tosyl alkenamides gave O‐cyclized products in good yields with high enantioselectivity. From the O‐cyclized products, a skeletal transformation was succeeded in the synthesis of biologically important chiral 8‐oxa‐6‐azabicyclo[3.2.1]octanes. DFT calculations suggested that the acetoxy anion

  一种新开发的氨基亚氨基苯氧基羧酸铜（L7 -Cu-OAc）催化的N-甲苯磺酰基烯酰胺的不对称碘环化反应，以高收率和高对映选择性提供了O环化产物。从O环化产物中，成功地合成了生物学上重要的手性8-氧杂-6-氮杂双环[3.2.1]辛烷。DFT计算表明，[ L7 -Cu-OAc]的乙酰氧基阴离子可作为生成N- Tosyl alkenamide底物阴离子的碱。交换的乙酸在催化剂和底物之间重建了新的氢键网络，从而实现了高效的不对称O-iodocyclization的Ñ -tosyl alkenamides。
• A trinuclear Zn₃(OAc)₄-3,3′-bis(aminoimino)binaphthoxide complex for highly efficient catalytic asymmetric iodolactonization
  作者：Takayoshi Arai、Noriyuki Sugiyama、Hyuma Masu、Sayaka Kado、Shinnosuke Yabe、Masahiro Yamanaka

  DOI：10.1039/c4cc02415j

  日期：——

  A 3,3'-bis(aminoimino)BINOL ligand was newly designed and synthesized for the formation of a trinuclear Zn complex upon reaction with Zn(OAc)2. Using the harmony of the tri-zinc atoms, 1 mol% Zn3(OAc)4-3,3'-bis(aminoimino)binaphthoxide catalyzed asymmetric iodolactonization in up to 99.9% ee.

  新设计并合成了3,3'-双（氨基亚氨基）BINOL配体，用于与Zn（OAc）2反应形成三核Zn络合物。使用三锌原子的和谐，1摩尔％Zn3（OAc）4-3,3'-双（氨基亚氨基）二萘嵌苯氧化物在不超过99.9％ee的条件下催化不对称碘代内酯化。
• JP2015/38052
  申请人：——

  公开号：——

  公开（公告）日：——
• Trans-1,2-diphenylethylene bridged salicylaldiminato–isoindoline titanium(IV) chloride complexes: Synthesis, characterization and catalytic polymerization
  作者：Li Wan、Dao Zhang、Quanrui Wang、Zhenxia Chen、Linhong Weng

  DOI：10.1016/j.jorganchem.2012.11.013

  日期：2013.1

  The tridentate ligands, 4-R1-6-R2-2-(trans-2-(isoindolin-2-yl)-1,2-diphenylethylimino) methyl} phenol (R-1 = R-2 = tert-butyl, 3a; R-1 = Ph, R-2 = H, 3b; R-1 = R-2 = H, 3c; R-1 = R-2 = Cl, 3d; R-1 = R-2 = Br, 3e; R-1 = R-2 = I, 3f) in which a substituted salicylaldiminato moiety and an isoindoline are linked by trans-1,2-diphenylethylene moiety have been prepared. Ligand 4-R1-6-R2-2-(trans-2-(isoindolin-2-yl)-1,2-diphenylethylamino) methyl} phenol (R-1 = R-2 = tert-butyl, 4a; R-1 = R-2 = I, 4f) was obtained from the reduction of 3a and 3f with NaBH4 in methanol/THF solution at low temperature. Deprotonation of these tridentate ligands 3a-f, 4a and 4f by NaH at -78 degrees C in THF, followed by treating with 1.2 equiv of TiCl4 in toluene at room temperature, afforded the desired dark red titanium complexes[Ti(L)Cl-3] (5a-f, 6a and 6f) in moderate to good yields. The structures of 5a and 6a were confirmed by single-crystal X-ray diffraction in the solid state. The metal atom has a distorted octahedral coordination geometry through the two nitrogen and one oxygen atoms from the tridentate ligand and three chlorides. These titanium complexes with such trans-1,2-diphenylethylene bridged tridentate ligands proved to be active to catalyze ethylene (co)polymerization with activity of 12.4-232.0 kg-polymer/mol(Ti).h. The C-13 NMR analysis of the polymer produced revealed that the polymer is highly linear polyethylene with no detectable branches and only very low amount of 1-hexene was incorporated into the main chain of the polyethylene. (C) 2012 Elsevier B. V. All rights reserved.
• NOVEL COMPOUND AND ANTIVIRAL AGENT CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：NATIONAL UNIVERSITY CORPORATION CHIBA UNIVERSITY

  公开号：US20170368015A1

  公开（公告）日：2017-12-28

  An object of the invention is to provide a compound that can be utilized as an antiviral agent, in particular as an anti-RNA viral agent, and especially as an anti-RS viral agent. The invention provides a compound indicated by Formula (1), wherein R1 each independently represent hydrogen, halogen, hydroxyl, amino, carboxyl, C1-C6 alkyl, C1-C6 alkoxyl, C1-C6 halogenoalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylamino, C2-C5 alkenyl, C3-C6 cycloalkyl, or optionally substituted aryl; R2 each independently represent hydrogen, C1-C6 alkyl, C1-C6 halogenoalkyl, C2-C5 alkenyl, C3-C6 cycloalkyl, optionally substituted aryl or heterocyclic group; and one or more R1 may be present in the same ring, an isomer thereof, a pharmaceutically acceptable salt thereof, or a mixture of these. The compounds provided by the invention are useful as drugs for the prevention or treatment of infectious diseases by virus, especially RS virus, and in particular infectious diseases in the lower airways (e.g., bronchiolitis, pneumonia, etc.).