(R)-N¹-methyl-1-phenylethane-1,2-diamine | 61337-91-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-N¹-methyl-1-phenylethane-1,2-diamine
• 英文别名: (R)-2-amino-1-(methylamino)-2-phenylethane；(4R)-phenyl-3-methyl-ethylenediamine；(1R)-N'-methyl-1-phenylethane-1,2-diamine
• CAS: 61337-91-5；79513-96-5；126179-86-0
• 化学式: C₉H₁₄N₂
• 分子量: 150.224
• InChiKey: KJYMPQAJEPMXKR-VIFPVBQESA-N

物化性质

• 沸点：
  257.8±20.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N¹-methyl-1-phenylethane-1,2-diamine 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.58h， 生成 (4R,12R)-6,10-dimethyl-2-oxo-4,12-diphenyl-1λ⁵,3,6,10-tetraazatricyclo[7.3.0.0^3,7]dodeca-1(9),7-dien-1-ylium chloride
  参考文献：
  名称：

  亚甲基桥联双（咪唑啉）衍生的 2-氧代嘧啶盐作为不对称迈克尔反应的催化剂

  摘要：

  一言以蔽之：具有平面氮中心的标题盐被成功地用作甘氨酸叔丁酯二苯甲酮席夫碱与乙烯基酮和查尔酮衍生物的不对称迈克尔反应的相转移催化剂，从而提供了极好的非对映和对映控制水平（见方案）。

  DOI：

  10.1002/anie.201300614
• 作为产物：
  描述：

  (S)-N-ethoxycarbonyl-2-phenylglycine 在 咪唑 、 亚磷酸三苯酯 、 氢溴酸 、 diborane(6) 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 12.0h， 生成 (R)-N¹-methyl-1-phenylethane-1,2-diamine
  参考文献：
  名称：

  Brienne; Jacques; Gayral, European Journal of Medicinal Chemistry, 1981, vol. 16, # 4, p. 363 - 366

  摘要：

  DOI：

文献信息

• The preparation of imidazolidinone and oxazolidinone chelated carbene complexes
  作者：Timothy S Powers、William D Wulff、John Quinn、Yan Shi、Weiqin Jiang、Richard Hsung、Mark Parisi、Annette Rahm、Xiao Wu Jiang、Glenn P.A Yap、Arnold L Rheingold

  DOI：10.1016/s0022-328x(00)00734-8

  日期：2001.1

  these complexes. The imidazolidinone complexes are best prepared by adding an imidazolidinone or lithiated imidazolidinone to a methoxy carbene complex or to an in-situ generated acetoxy carbene complex. α,β-Unsaturated imidazolidinone complexes are prepared by aldol condensations of alkyl imidazolidinone complexes or by alkylaltion of these complexes with bromomethyl methyl ether and then elimination

  （CO）4 M = CC（R 1）NCO（CHR 2 CHR 3 X）类型的几种内部螯合的咪唑啉酮和恶唑烷酮费希尔卡宾配合物的合成据报道，其中M =铬，钨；[R 1 =甲基，乙基，异丙基，苯基，反式-丙烯基，异丙烯基，异丁烯基，环己烯基和1-丙炔基; R 2＝ H，Ph，Bn，Me，Cy；R 3= H，我，Ph；X = O，NMe。四种不同的方法用于合成这些配合物。最好将咪唑烷酮或锂化的咪唑烷酮加入甲氧基卡宾配合物或原位生成的乙酰氧基卡宾配合物中来制备咪唑烷酮配合物。α，β-不饱和咪唑烷酮配合物是通过烷基咪唑烷酮配合物的羟醛缩合或通过将这些配合物与溴代甲基甲醚烷基化，然后除去甲醇而制备的。最佳的恶唑烷酮配合物是通过两步程序制备的，该过程包括向甲氧基或乙酰氧基配合物中添加β-氨基醇，然后用光气将所得的氨基卡宾配合物封闭到恶唑烷酮配合物中。
• Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines
  作者：Andrei V. Malkov、Angus J. P. Stewart-Liddon、Grant D. McGeoch、Pedro Ramírez-López、Pavel Kočovský

  DOI：10.1039/c2ob25472g

  日期：——

  A new family of Lewis basic 2-pyridyl oxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyl oxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high

  已经开发了一个新的Lewis碱性2-吡啶基恶唑啉家族，该家族可作为有效的有机催化剂，用于对映体选择性还原前手性芳族酮和酮亚胺与 三氯硅烷，一种容易获得且便宜的试剂。 1-异喹啉基恶唑啉，源于 扁桃酸被认为是该系列中最有效的催化剂，能够在降低酮类（最多94％ee）和酮酮（最多89％ee）方面提供高对映选择性。
• New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents
  作者：Andrey E. Sheshenev、Ekaterina V. Boltukhina、Anastasiya A. Grishina、Ivana Cisařova、Ilya M. Lyapkalo、King Kuok Mimi Hii

  DOI：10.1002/chem.201300062

  日期：2013.6.17

  A family of new chiral zwitterionic phosphorus‐containing heterocycles (zPHC) have been derived from methylene‐bridged bis(imidazolines). These structures were unambiguously determined, including single‐crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed

  一个新的手性两性离子含磷杂环（zPHC）家族衍生自亚甲基桥双（咪唑啉）。明确确定了这些结构，包括对两种化合物的单晶XRD分析。随后研究了这些偶极磷杂环的稳定性，酸/碱和电子性质。zPHCs可以成功地用作一类新的手性溶剂化剂，用于通过NMR光谱对手性羧酸和磺酸进行对映异构化。通过NMR滴定法确定了形成的供体-受体复合物的化学计量和结合常数。
• Organocatalytic Asymmetric Michael Reaction of Cyclic 1,3-Dicarbonyl Compounds andα,β-Unsaturated Ketones—A Highly Atom-Economic Catalytic One-Step Formation of Optically Active Warfarin Anticoagulant
  作者：Nis Halland、Tore Hansen、Karl Anker Jørgensen

  DOI：10.1002/anie.200352136

  日期：2003.10.20
• CATALYSTS
  申请人：Goldenkeys High-Tech Materials Co., Ltd.

  公开号：US20220235082A1

  公开（公告）日：2022-07-28

  A compound, e g a diamine ligand, represented by the following general formula (1): (Formula (1)) wherein each * represents an asymmetric carbon atom; X represents a group selected from one of an ester (e.g. a t-butyl ester); a thioester; an amide; a heterocyclic moiety (e.g. a five-membered heterocyclic ring) comprising one or more of O, S, Se, and/or P (e.g. a furan, a tetrahydrofuran, a thiophene, an isoxazole, a bromo-furan, or a thiazole); a moiety (e.g. a five-membered heterocyclic ring) comprising a nitrogen atom, wherein the nitrogen atom is protected with a protecting group containing an electron-withdrawing group, preferably the protecting group is selected from one of a carbamate protecting group, an amide protecting group, an aryl sulphonamide protecting group, or an alkyl sulphonamide protecting group; and optionally X may additionally comprise a solid support, e.g. a polymeric or a silica particle; Y represents or is CtT′T″ where ‘t’ is 0 or 1 and when ‘t’ is 1 T′ and T″ may individually represent a substituent, e.g. if t is 1, T′ and/or T″ may each be hydrogen or deuterium atom, or a halogen atom; for example, Y may represent a carbon atom comprising two further substituents; Z represents a hydrogen atom or a deuterium atom; R 1 represents an alkyl group (e.g. a functionalised alkyl group) preferably having between 1 to 100 carbon atoms, for example, between 1 to 30 carbon atoms (e.g. 1 to 20 carbon atoms, or 1 to 10 carbon atoms), a halogenated alkyl group preferably having between 1 to 100 carbon atoms (e.g. CF 3 ), for example, between 1 to 30 carbon atoms (e.g. 1 to 20 carbon atoms, or 1 to 10 carbon atoms), an aryl group preferably having between 5 to 100 carbon atoms, e.g. 6 to 30 carbon atoms and optionally having one or more substituents selected from alkyl groups preferably having 1 to 100 carbon atoms, e.g. 1 to 10 carbon atoms, halogenated alkyl groups preferably having 1 to 100 carbon atoms, e.g. 1 to 10 carbon atoms, and/or halogen atoms; or R 1 represents a solid support, e.g. a silica particle or a polymeric particle; R 2 and R 3 each independently represent a group selected from alkyl groups preferably having between 1 to 100 carbon atoms, for example 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), aryl groups (e.g. phenyl groups), and cycloalkyl groups preferably having 3 to 8 carbon atoms, the aryl group or phenyl group optionally having one or more substituents selected from alkyl groups preferably having between 1 to 100 carbon atoms, e.g. between 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), alkoxy groups preferably having between 1 to 100 carbon atoms, for example, between 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), and halogen atoms, and each hydrogen atom of the cycloalkyl groups being optionally replaced by an alkyl group preferably having between 1 to 100 carbon atoms, e.g. 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), or R 1 represents a polyethylene glycol (PEG) moiety having the formula C 2n H 4n+2 O n+1 wherein n is an integer between 1 and 100; or R 2 and R 3 form a ring together with carbon atoms to which R 2 and R 3 are bonded; R 4 represents a hydrogen atom or a deuterium atom.