(+)-(2S,2'S,2''S)-triisopropanolamine | 83023-82-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+)-(2S,2'S,2''S)-triisopropanolamine
• 英文别名: (+)-(S,S,S)-triisopropanolamine；(S,S,S)-(+)-triisopropanolamine；(S,S,S)-tri-2-propanolamine；(S,S,S)-triisopropanolamine；(S,S,S)-tris-2-propanolamine；(2S)-1-[bis[(2S)-2-hydroxypropyl]amino]propan-2-ol
• CAS: 83023-82-9
• 化学式: C₉H₂₁NO₃
• 分子量: 191.271
• InChiKey: SLINHMUFWFWBMU-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三正丁基甲氧基锡 、 (+)-(2S,2'S,2''S)-triisopropanolamine 以 苯 为溶剂， 生成 tris(2-tributylstannoxypropyl)amine
  参考文献：
  名称：

  Synthesis and Characterisation of 1-[9-(H, Me3Si, Me3Ge, Me3Sn)9-Fluorenyl]-3,7,10-trimethylgermatranes. The Crystal Structure Analysis of 1-(9-Fluorenyl)-3,7,10-trimethylgermatrane

  摘要：

  The title compounds, viz. C13H8(R)Ge . (OCHMeCH2)(3)N (1: R = H, 2: R = Me3Si; 3: R = Me3Ge) were prepared as mixtures of diastereomers by the reaction of N(CH(2)CHMeOSnAlk(3))(3) (7: Alk = Et; 8: Alk = Bu) with C13H8(R)GeBr3 (4: R=H, 5: R=Me3Si; 6: R=Me3Ge), respectively. The synthesis of C13H8(Me3Sn)Ge (OCHMeCH2)(3)N (13) by the reaction of germatrane (1) with Me3SnNMe2 is reported. Identity and structures were established by elemental analyses,H-1 and C-13 NMR spectroscopy and mass spectrometry. The crystal structure of 1 was determined by X-ray diffraction methods.

  DOI：

  10.1002/(sici)1521-3749(199904)625:4<655::aid-zaac655>3.0.co;2-n
• 作为产物：
  描述：

  S-环氧丙烷 在 氨 作用下， 以 水 为溶剂， 反应 24.0h， 以71.7%的产率得到(+)-(2S,2'S,2''S)-triisopropanolamine
  参考文献：
  名称：

  （+）-（3 S，7 S，10 S）-和（+）-（3 S，7 S，10 R）-3,7,10-三甲基硼烷的合成。反应中对映体纯度的扩增

  摘要：

  描述了两种对映体纯的异构体（+）-（3 S，7 S，10 S）-和（+）-（3 S，7 S，10 R）-3,7,10-三甲基硼酸酯的合成通过1 H和13 C-NMR光谱确定。提出了一种通过部分溶解的（S）环氧丙烷的三聚反应提高对映体纯度的方法。从动力学角度研究了该反应，并根据二项式概率方案对其进行了解释。实验结果表明（SSS）三聚体与起始材料相比，而（SSR）三聚体没有发现增加。

  DOI：

  10.1016/s0040-4020(01)83483-9
• 作为试剂：
  描述：

  叠氮基三甲基硅烷 、 氧化环己烯 在 三氟乙酸三甲基硅酯 、 zirconium(IV) tert-butoxide 、 (+)-(2S,2'S,2''S)-triisopropanolamine 作用下， 以 二氯甲烷 为溶剂， 生成 O-trimethylsilyl-2-azido-cyclohexanol 、 ((2-azidocyclohexyl)oxy)trimethylsilane
  参考文献：
  名称：

  Mechanistic Studies of the Zirconium−Triisopropanolamine-Catalyzed Enantioselective Addition of Azide to Cyclohexene Oxide

  摘要：

  The mechanism of the enantioselective ring-opening of cyclohexene oxide by Me3SiN3, catalyzed by zirconium complexes of the C-3-symmetric ligand (+)-(S,S,S)-triisopropanolamine, has been investigated. Measurements of molecular weights of precatalyst species show that complexes are formed with average trimeric aggregation. Kinetics measurements reveal the overall process to be approximately half order in total zirconium, epoxide, and Me3SiN3 components. The reaction also shows a strong nonlinear relationship between enantiomeric excess of product azido ether vs the incorporation of (R,S,S)-triisopropanolamine ligand in the catalyst mixture. On the basis of these and other results, a preequilibrium interconversion of dimeric and tetrameric zirconium-triisopropanolamine species is proposed to occur rapidly with respect to the rate of epoxide ring-opening, with the dimeric form being the active catalyst. The reaction is accelerated by silyl ethers or by small amounts of water or alcohol, whereas larger amounts of protic additives inhibit the reaction. Enantioselectivity is eroded at catalyst concentrations less than 1 mole-percent and at high concentrations of cyclohexene oxide. Both enantioselectivity and rate are influenced to a small extent by the nature of the silyl azide employed for the first catalytic turnover, suggesting that a silyl fragment becomes irreversibly incorporated in the catalyst structure. It is proposed that catalytic activity requires the cooperative action of two zirconium centers for the binding and delivery of azide to epoxide.

  DOI：

  10.1021/jo9809377

文献信息

• Metal-organic frameworks containing nitrogen-donor ligands for efficient catalytic organic transformations
  申请人：The University of Chicago

  公开号：US10647733B2

  公开（公告）日：2020-05-12

  Metal-organic framework (MOFs) compositions based on nitrogen donor-based organic bridging ligands, including ligands based on 1,3-diketimine (NacNac), bipyridines and salicylaldimine, were synthesized and then post-synthetically metalated with metal precursors, such as complexes of first row transition metals. Metal complexes of the organic bridging ligands could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

  基于以氮为供体的有机桥联配体，包括基于1,3-二酮亚胺（NacNac）、联吡啶和柳酸亚胺的金属-有机框架（MOFs）组成物被合成，然后用金属前驱体如第一行过渡金属的络合物进行后合成金属化。有机桥联配体的金属络合物也可以直接并入MOFs中。MOFs提供了一个多功能的、可回收和可重复使用的单点固体催化剂家族，用于催化各种不对称有机转化。这些固体催化剂也可以集成到流动反应器或超临界流体反应器中。
• Homogeneous asymmetric hydrogenation catalyst
  申请人：Shimizu Hideo

  公开号：US20090203927A1

  公开（公告）日：2009-08-13

  Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.

  提供一种用于均相氢化的有用催化剂，特别是用于均相不对称氢化的催化剂，特别是不对称氢化的催化剂，该催化剂易于获得，在经济性和可操作性方面表现出色，以及一种使用该催化剂产生不饱和化合物的氢化物的方法，特别是使用高产率和光学纯度的该催化剂产生手性活性化合物。
• Use of electrospray ionization mass spectrometry to characterize chiral reactive intermediates in a titanium alkoxide mediated sulfoxidation reaction
  作者：Marcella Bonchio、Giulia Licini、Giorgio Modena、Stefano Moro、Olga Bortolini、Piero Traldi、William A. Nugent

  DOI：10.1039/a701227f

  日期：——

  The ESIMS technique, combined with 1 H NMR evidence, provides a precise inventory of the catalytic Ti IV precursors and the characterization of the reactive peroxometal complex involved in enantioselective sulfoxidation employing the Ti IV –homochiral trialkanolamine–alkylhydroperoxide system.

  ESIMS 技术与 1 H NMR 证据相结合，提供了催化 Ti IV 前体的精确清单，并描述了采用 Ti IV - 同手性三烷醇胺 - 烷基过氧化氢体系进行对映选择性硫氧化作用时所涉及的活性过氧金属复合物的特征。
• New Titanatranes:  Characterization and Styrene Polymerization Behavior
  作者：Youngjo Kim、Yonggyu Han、Jeong-Wook Hwang、Myong Woon Kim、Youngkyu Do

  DOI：10.1021/om0109197

  日期：2002.3.1

  they exist in the monomeric form in the solid state and the Ti atom adopts essentially an η5 bonding posture with the Cp‘ ring and a tetradentate bonding mode with the trialkanolatoamine ligand via a transannular interaction from the bridgehead N atom to Ti. All compounds show very high catalytic activity for the syndiospecific polymerization of styrene in the presence of modified methylaluminoxane

  在三乙胺的存在下，通过各种三烷醇胺与（C 5 Me 4 R）TiCl 3（Cp'= C 5 Me 4 R）的反应，制备了含有环戊二烯基配体的新的钛烷烃。X射线分析表明，它们在单体形式存在于固态和钛原子基本上采用一个η 5与CP”环接合姿势并与来自含有桥头氮的trialkanolatoamine配体经由一个跨环相互作用四齿键合方式钛原子。在改性甲基铝氧烷（MMAO）助催化剂的存在下，所有化合物均表现出很高的催化苯乙烯间间聚合反应的催化活性。
• Dimolybdenum Bis((<i>S</i>,<i>S</i>,<i>S</i>)-triisopropanolaminate(3−)):  A Blue Compound with an Unusual Mo−Mo Triple Bond
  作者：Malcolm H. Chisholm、Ann M. Macintosh、John C. Huffman、Dedong Wu、Ernest R. Davidson、Robin J. H. Clark、Steven Firth

  DOI：10.1021/ic991352d

  日期：2000.8.1

  Mo2(OtBu)6 and Mo2(NMe2)6 each react with (S,S,S)-triisopropanolamine (2 equiv) in benzene to yield dimolybdenum bis((S,S,S)-isopropanolaminate(3-)), Mo2[(OC-(S)-HMeCH2)3N]2 (M identical to M), as a blue crystalline solid. Cell parameters at -160 degrees C: a = 17.389(6) A, b = 10.843(3) A, c = 10.463(3) A, beta = 125.28(1) degrees, Z = 2 in space group C2. The molecular structure involves an Mo2 unit

  Mo2（OtBu）6和Mo2（NMe2）6各自与（S，S，S）-三异丙醇胺（2当量）在苯中的反应生成二钼双（（S，S，S）-异丙醇胺化（3-）），Mo2 [（OC-（S）-HMeCH2）3N] 2（M与M相同），为蓝色结晶固体。在-160度C下的像元参数：空间组C2中a = 17.389（6）A，b = 10.843（3）A，c = 10.463（3）A，beta = 125.28（1）度，Z = 2。分子结构涉及O6N2扭曲立方箱内部的Mo2单元。Mo2轴在三个位置上的混乱度约为ca。45％，45％和10％。尽管存在这种紊乱，但显示出分子结构包含与距离为2.15（3）的Mo单元相同的中心Mo，与两个三羟甲基配体配位，每个配体具有两个螯合臂，一个跨越Mo且与Mo键相同。局部Mo2O6N2部分具有近似C2h对称性，且Mo-N距离很长，为2.4A。苯-d6中记录的1H和13C（1H）NMR光谱