2-morpholino-N-(2-(phenylthio)ethyl)ethylamine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-morpholino-N-(2-(phenylthio)ethyl)ethylamine
• 英文别名: 2-(4-morpholinyl)-N-(2-phenylthioethyl)ethylamine；2-Morpholino-N-[2-(phenylthio)ethyl]ethan-1-amine；2-morpholin-4-yl-N-(2-phenylsulfanylethyl)ethanamine
• 化学式: C₁₄H₂₂N₂OS
• mdl: MFCD13206174
• 分子量: 266.407
• InChiKey: QZXXNGSHWPYOBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tris(triphenylphosphine)ruthenium(II) chloride 、 2-morpholino-N-(2-(phenylthio)ethyl)ethylamine 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到2-morpholin-4-yl-N-(2-phenylsulfanylethyl)ethanamine;ruthenium(2+);triphenylphosphane;dichloride
  参考文献：
  名称：

  [EN] POLYDENTATE LIGANDS AND THEIR COMPLEXES FOR MOLECULAR CATALYSIS
  [FR] LIGANDS POLYDENTATES ET LEURS COMPLEXES POUR LA CATALYSE MOLÉCULAIRE

  摘要：

  本发明涉及新型的无手性和手性硫、氮和磷含配体，被称为NNS型、P(0)NS型、PNS型、SNNS型、SNNP(0)型或SNNP型多齿配体以及这些配体的过渡金属配合物。从这些配体和过渡金属配合物衍生的催化剂可用于各种催化反应，包括不饱和有机化合物的加氢和转移加氢、醇和硼烷的脱氢、各种脱氢偶联反应以及其他催化转化。

  公开号：

  WO2015191505A1
• 作为产物：
  描述：

  2-苯硫基乙醇 在 三溴化磷 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.75h， 生成 2-morpholino-N-(2-(phenylthio)ethyl)ethylamine 、 2-morpholino-N,N-bis(2-(phenylthio)ethyl)ethylamine
  参考文献：
  名称：

  [EN] POLYDENTATE LIGANDS AND THEIR COMPLEXES FOR MOLECULAR CATALYSIS
  [FR] LIGANDS POLYDENTATES ET LEURS COMPLEXES POUR LA CATALYSE MOLÉCULAIRE

  摘要：

  本发明涉及新型的无手性和手性硫、氮和磷含配体，被称为NNS型、P(0)NS型、PNS型、SNNS型、SNNP(0)型或SNNP型多齿配体以及这些配体的过渡金属配合物。从这些配体和过渡金属配合物衍生的催化剂可用于各种催化反应，包括不饱和有机化合物的加氢和转移加氢、醇和硼烷的脱氢、各种脱氢偶联反应以及其他催化转化。

  公开号：

  WO2015191505A1

文献信息

• First-row transition metal complexes of ENENES ligands: the ability of the thioether donor to impact the coordination chemistry
  作者：Pavel A. Dub、Brian L. Scott、John C. Gordon

  DOI：10.1039/c5dt03855c

  日期：——

  metal atom. In the case of a less basic SPh moiety, a bidentate coordination mode was identified for harder metals (Mn, Fe), whereas a tridentate coordination mode was identified in the case of a more basic SBn moiety with softer metals (Ni, Cu). In the intermediate case of Co, ligands a and b coordinate via κ2[N,N′] and κ3[N,N′,S] coordination modes, which can be conveniently predicted by DFT calculations

  ENENES配体的两个变体E（CH 2）2 NH（CH）2 SR（其中E = 4-吗啉基，R = Ph（a），Bn（b）与MCl 2（M = Mn，Fe，配位溶剂（MeCN，EtOH）中的Co，Ni和Cu）提供可分离的络合物，其磁化率测量结果表明顺磁性和高自旋配方。可用的晶体的X射线衍射研究表明，该配体与金属配位在任何一个二齿κ 2 [ Ñ，Ñ ']或三齿κ 3 [ Ñ，Ñ '，小号取决于配体的性质和/或金属原子的身份。对于碱性较低的SPh部分，对于较硬的金属（Mn，Fe），鉴定为双齿配位模式，而对于碱性较高的SBn与较软的金属（Ni，Cu），则鉴定为三齿配位模式。在Co的中间的情况下，配体一和b坐标经由κ 2 [ Ñ，Ñ ']和κ 3 [ Ñ，Ñ '，小号]的配位模式，这可以通过DFT计算而方便地进行预测。为最柔软的金属（Cu）的，配位体一在κ坐标3[ N，N '，S ]时尚。
• Polydentate ligands and their complexes for molecular catalysis
  申请人：Triad National Security, LLC

  公开号：US10550139B2

  公开（公告）日：2020-02-04

  Embodiments of the present disclosure relate generally to novel achiral and chiral sulfur-, nitrogen- and phosphorus-containing ligands, designated as NNS-type, P(O)NS-type, PNS-type, SNNS-type, SNNP(O)-type, or SNNP-type polydentate ligands and transition metal complexes of these ligands, including iridium complexes having PNS-type and NNS-type ligands. The catalysts derived from these ligands and transition metal complexes may be used in a wide range of catalytic reactions, including hydrogenation and transfer hydrogenation of unsaturated organic compounds, dehydrogenation of alcohols and boranes, various dehydrogenative couplings, chemoselective hydrogenation of α,β-unsaturated alcohols, and other catalytic transformations.

  本公开的实施方案一般涉及新型非手性和手性含硫、氮和磷配体，即NNS型、P(O)NS型、PNS型、SNNS型、SNNP(O)型或SNNP型多齿配体以及这些配体的过渡金属配合物，包括具有PNS型和NNS型配体的铱配合物。由这些配体和过渡金属配合物衍生的催化剂可用于多种催化反应，包括不饱和有机化合物的氢化和转移氢化、醇和硼烷的脱氢、各种脱氢偶联反应、α,β-不饱和醇的化学选择性氢化以及其他催化转化反应。
• Air-Stable NNS (ENENES) Ligands and Their Well-Defined Ruthenium and Iridium Complexes for Molecular Catalysis
  作者：Pavel A. Dub、Brian L. Scott、John C. Gordon

  DOI：10.1021/acs.organomet.5b00432

  日期：2015.9.28

  We introduce ENENES, a new family of air-stable and low-cost NNS ligands bearing NH functionalities of the general formula E(CH2)(m)NH(CH2)(n)SR, where E is selected from -NC4H8O, -NC4H8, or -N(CH3)(2), m and n = 2 and/or 3, and R = Ph, Bn, Me, or SR (part of a thiophenyl fragment). The preparation and characterization of more than 15 examples of well-defined Ru and Ir complexes supported by these ligands that are relevant to bifunctional metalligand M/NH molecular catalysis are reported. Reactions of NNS ligands with suitable Ru or Ir precursors afford rich and diverse solid-state and solution chemistries, producing monometallic molecules as well as bimetallics in which the ligand coordinates to the metal via either bidentate (kappa(2)[N,N'] or kappa(2)[N',S]) or tridentate (kappa(3)[N,N',S]) binding modes, depending on the basicity of the sulfur atom, CH2 chain length (m or n parameter), or identity of the transition metal. In the case of Ir, ligands bearing benzyl substituents lead to unprecedented kappa(4)[N,N',S,C]-tetradentate core-structure complexes of the type [(IrHCl)-H-IIIkappa(4)(N,N',S,C)ligand}], resulting from ortho-metalation via CH oxidative addition. Fourteen of these Ru and Ir complexes have been crystallographically characterized. Air- and moisture-stable complexes of the type trans-[(RuCl2)-Cl-IIkappa(3)[N,N',S]ligand}(L)] (L = PPh3, PCy3, DMSO), and others, effect the selective hydrogenation of methyl trifluoroacetate into the important synthon trifluoroacetaldehyde methyl hemiacetal in basic methanol under relatively mild conditions (3540 degrees C, 25 bar H-2) with reasonable turnover numbers (i.e., > 1000), whereas the air-stable Ir monohydride complexes [(IrHCl)-H-IIIkappa(4)(N,N',S,C)ligand}] exhibit excellent catalytic activities and high chemoselectivity for the same reaction, reaching turnover numbers of >10 000.
• Well-Defined ENENES Re and Mn Complexes and Their Application in Catalysis: The Role of Potassium <i>tert</i>-Butoxide
  作者：Liana Ribeiro Gouveia、Elon A. Ison

  DOI：10.1021/acs.organomet.2c00261

  日期：2022.10.10
• POLYDENTATE LIGANDS AND THEIR COMPLEXES FOR MOLECULAR CATALYSIS
  申请人：Los Alamos National Security, LLC

  公开号：US20170088571A1

  公开（公告）日：2017-03-30

  Embodiments of the present disclosure relate generally to novel achiral and chiral sulfur-, nitrogen- and phosphorus-containing ligands, designated as NNS-type, P(O)NS-type, PNS-type, SNNS-type, SNNP(O)-type, or SNNP-type polydentate ligands and transition metal complexes of these ligands, including iridium complexes having PNS-type and NNS-type ligands. The catalysts derived from these ligands and transition metal complexes may be used in a wide range of catalytic reactions, including hydrogenation and transfer hydrogenation of unsaturated organic compounds, dehydrogenation of alcohols and boranes, various dehydrogenative couplings, chemoselective hydrogenation of α,β-unsaturated alcohols, and other catalytic transformations.