(2R)-N,N-dibenzyl-2-aminobutan-1-ol | 249922-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-N,N-dibenzyl-2-aminobutan-1-ol
• 英文别名: (2R)-2-[Bis(phenylmethyl)amino]-1-butanol；(2R)-2-(dibenzylamino)butan-1-ol
• CAS: 249922-61-0
• 化学式: C₁₈H₂₃NO
• 分子量: 269.387
• InChiKey: RWDGCGHIPSWDTF-GOSISDBHSA-N

物化性质

• 沸点：
  388.4±22.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-N,N-dibenzyl-2-aminobutan-1-ol 在 zinc(II) tetrahydroborate 、 仲丁基锂 、 sodium hydride 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 环己烷 为溶剂， 反应 22.0h， 生成 (1S,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol
  参考文献：
  名称：

  Stereoselective Deprotonation of Chiral and Achiral 2-Aminoalkyl Carbamates: Synthesis of Optically Active β-Amino Alcohols via 1-Oxy-Substituted Alkyllithium Intermediates

  摘要：

  DOI：

  10.1055/s-1999-3575
• 作为产物：
  描述：

  2-氨基丁醇 、 溴甲苯 在 sodium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以100%的产率得到(2R)-N,N-dibenzyl-2-aminobutan-1-ol
  参考文献：
  名称：

  对映异构纯 [1,2-二氨基-1-（4-氟苯基）丁烷] 铂 (II) 复合物：合成和抗 MCF-7 和 MDA-MB 231 乳腺癌和 LnCaP/FGC 前列腺癌细胞系的抗肿瘤活性

  摘要：

  对映异构纯 1, 2-diamino-1- (4-fluorophenyl) 丁烷是通过立体选择性程序合成的。在用（1R）-肉豆蔻醛衍生化后，通过 1H NMR 光谱测定对映体纯度。为了与铂配位，二胺与 K2PtI4 反应。与 Ag2SO4 反应产生相应的硫酸合铂 (II) 配合物，通过用 2N HCl 处理将其转化为二氯铂 (II) 配合物。在MCF-7和MDA-MB 231乳腺癌细胞系以及LnCaP/FGC前列腺癌细胞系上研究了构型和离去基团种类对抗肿瘤活性的影响。结果表明，二氯铂 (II) 复合物比各自的二碘铂 (II) 衍生物更具活性。转化为硫酸铂 (II) 复合物进一步增强了抗增殖作用。该配置决定了抗肿瘤作用，取决于所使用的细胞系：MCF-7：(R, R)> (S, S)> (R, S)> (S, R)；MDA-MB 231：（S，S）>（R，R）>（R，S）=（S，R）；LnC

  DOI：

  10.1002/ardp.200400621

文献信息

• Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl)butane]platinum(II) Complexes: Synthesis and Antitumor Activity against MCF-7 and MDA-MB 231 Breast Cancer and LnCaP/FGC Prostate Cancer Cell Lines
  作者：Anja Dullin、Francois Dufrasne、Michael Gelbcke、Ronald Gust

  DOI：10.1002/ardp.200400621

  日期：2004.12

  Enantiomerically pure 1, 2‐diamino‐1‐(4‐fluorophenyl)butanes were synthesized by stereoselective procedures. The enantiomeric purity was determined by 1H NMR spectroscopy after derivatization with (1R)‐myrtenal. For the coordination to platinum, the diamines were reacted with K2PtI4. Reaction with Ag2SO4 yielded the respective sulfatoplatinum(II) complexes, which were converted into the dichloroplatinum(II)

  对映异构纯 1, 2-diamino-1- (4-fluorophenyl) 丁烷是通过立体选择性程序合成的。在用（1R）-肉豆蔻醛衍生化后，通过 1H NMR 光谱测定对映体纯度。为了与铂配位，二胺与 K2PtI4 反应。与 Ag2SO4 反应产生相应的硫酸合铂 (II) 配合物，通过用 2N HCl 处理将其转化为二氯铂 (II) 配合物。在MCF-7和MDA-MB 231乳腺癌细胞系以及LnCaP/FGC前列腺癌细胞系上研究了构型和离去基团种类对抗肿瘤活性的影响。结果表明，二氯铂 (II) 复合物比各自的二碘铂 (II) 衍生物更具活性。转化为硫酸铂 (II) 复合物进一步增强了抗增殖作用。该配置决定了抗肿瘤作用，取决于所使用的细胞系：MCF-7：(R, R)> (S, S)> (R, S)> (S, R)；MDA-MB 231：（S，S）>（R，R）>（R，S）=（S，R）；LnC
• Design, synthesis and biological evaluation of 6-pyridylmethylaminopurines as CDK inhibitors
  作者：Stuart C. Wilson、Butrus Atrash、Clare Barlow、Susan Eccles、Peter M. Fischer、Angela Hayes、Lloyd Kelland、Wayne Jackson、Michael Jarman、Amin Mirza、Javier Moreno、Bernard P. Nutley、Florence I. Raynaud、Peter Sheldrake、Mike Walton、Robert Westwood、Steven Whittaker、Paul Workman、Edward McDonald

  DOI：10.1016/j.bmc.2011.08.051

  日期：2011.11

  The cyclin-dependent kinase (CDK) inhibitor seliciclib (1, CYC202) is in phase II clinical development for the treatment of cancer. Here we describe the synthesis of novel purines with greater solubility, lower metabolic clearance, and enhanced potency versus CDKs. These compounds exhibit novel selectivity profiles versus CDK isoforms. Compound alpha SbR-21 inhibits CDK2/cyclin E with IC(50) = 30 nM, CDK7-cyclin H with IC(50) = 1.3 mu M, and CDK9-cyclinT with IC(50) = 0.11 mu M; it (CCT68127) inhibits growth of HCT116 colon cancer cells in vitro with GI(50) = 0.7 mu M; and shows antitumour activity when dosed p.o. at 50 mg/kg to mice bearing HCT116 solid human tumour xenografts. (C) 2011 Elsevier Ltd. All rights reserved.
• 4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors
  作者：Shigeo Ueda、Hideo Terauchi、Akihiro Yano、Masashi Matsumoto、Taeko Kubo、Yoko Kyoya、Kenji Suzuki、Motoharu Ido、Motoji Kawasaki

  DOI：10.1016/j.bmc.2004.05.031

  日期：2004.8.1

  In the course of our search for selective iNOS inhibitors, we have previously reported that 2-imino-1,3-oxazolidine derivatives (1) and 2-aminothiazole derivatives (2) are selective iNOS inhibitors. In order to find more potent iNOS inhibitors, we focused our efforts on the synthesis and evaluation of the inhibitory activity against iNOS and selectivity for iNOS both in vitro and in vivo of a series of 2-imino-1,3-thiazolidine derivatives (3), which are analogues of I and 2. Our results show that among the compounds synthesized (4R,5R)-5-ethyl-2-imino-4-methyl-1,3-thiazolidine [(4R,5R)-14a: ES-1537] exhibited potent inhibitory activity and selectivity for iNOS. In addition, ES-1537 had good pharmacokinetic profile in rats with BA value of 80%. It is therefore expected that ES-1537 may be therapeutically useful for the treatment of diseases related to excess production of NO. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol – The crucial role of the configuration
  作者：Georgi M. Dobrikov、Violeta Valcheva、Margarita Stoilova-Disheva、Georgi Momekov、Pavleta Tzvetkova、Angel Chimov、Vladimir Dimitrov

  DOI：10.1016/j.ejmech.2011.11.035

  日期：2012.2

  The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 mu M-14.03 mu M. Five of the most active compounds 11, 22, 23, 31 and 42(5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H(37)Rv showing no activity even at 20-32 fold higher concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Stereoselective Deprotonation of Chiral and Achiral 2-Aminoalkyl Carbamates: Synthesis of Optically Active β-Amino Alcohols via 1-Oxy-Substituted Alkyllithium Intermediates
  作者：Jörg Schwerdtfeger

  DOI：10.1055/s-1999-3575

  日期：1999.9