3-(Benzylamino)-1-phenyl-1-propanol | 34597-73-4

• 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: 3-(Benzylamino)-1-phenyl-1-propanol
• 英文别名: N-benzyl-1-phenyl-3-aminopropan-1-ol；3-(benzylamino)-1-phenylpropan-1-ol；3-benzylamino-1-phenylpropan-1-ol
• CAS: 34597-73-4
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: LNUDPASEMGLGKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  56.3-57.6 °C
• 沸点：
  401.6±40.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Benzylamino)-1-phenyl-1-propanol 在 palladium on activated charcoal 、 镍 sodium hydroxide 、 sodium azide 、 氨 、 氢气 、 sodium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 、 正丁醇 为溶剂， 20.0~80.0 ℃ 、600.0 kPa 条件下， 反应 78.0h， 生成 2-[4-[Benzyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropyl]amino]butylcarbamoyloxy]acetic acid
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm991043x
• 作为产物：
  描述：

  1-苯丙醇 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 palladium 10% on activated carbon 、 氢气 、 氯苯 、 三甲基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 20.0~100.0 ℃ 、506.66 kPa 条件下， 反应 70.0h， 生成 3-(Benzylamino)-1-phenyl-1-propanol
  参考文献：
  名称：

  Transformation of α-Substituted Propanols into γ-Amino Alcohols through Nickel-Catalyzed Amination on the Terminal γ-Carbon of Propanols

  摘要：

  研究发现，镍膦络合物可作为催化剂，有效地将醇转化为δ-烯丙酮，再通过传统还原剂将δ-烯丙酮连续转化为δ-氨基醇。这种连续转化相当于在饱和醇的δ³位形成碳氮键。

  DOI：

  10.1055/s-0030-1260536

文献信息

• Catalytic Enantio- and Diastereoselective Alkylations with Cyclic Sulfamidates
  作者：Thomas A. Moss、Beatriz Alonso、David R. Fenwick、Darren J. Dixon

  DOI：10.1002/anie.200905329

  日期：2010.1.12

  Open for business: The enantio‐ and diastereoselective nucleophilic ring opening of five‐membered and six‐membered cyclic sulfamidates under asymmetric phase‐transfer catalysis is presented. A range of pro‐nucleophiles have been successfully alkylated in good yields and in good to excellent enantioselectivites.

  营业时间：介绍了在不对称相转移催化下五元和六元环状氨基磺酸盐的对映体和非对映体选择性亲核开环。一系列亲核亲核试剂已成功烷基化，收率高，对映体选择性优良。
• Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence
  作者：Adam D. J. Calow、Andrei S. Batsanov、Elena Fernández、Cristina Solé、Andrew Whiting

  DOI：10.1039/c2cc36129a

  日期：——

  An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β-unsaturated imine formation, β-boration, reduction (CN) and oxidation (C–B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added to directly access the corresponding 1,3-oxazine derivatives.

  开发了一种高效的四步一锅法高度立体选择性合成γ-氨基醇的路线，通过原位形成α，β-不饱和亚胺、β-硼化、还原（CN）和氧化（C-B）的顺序，特别是对于某些水溶性γ-氨基醇，还可以增加一步直接获得相应的1,3-噁嗪衍生物。
• Catalytic Asymmetric Alkylation Reactions for the Construction of Protected Ethylene-Amino and Propylene-Amino Motifs Attached to Quaternary Stereocentres
  作者：Thomas A. Moss、David M. Barber、Andrew F. Kyle、Darren J. Dixon

  DOI：10.1002/chem.201203825

  日期：2013.2.25

  An efficient catalytic and stereoselective method for the direct construction of protected ethylene‐amino and propylene‐amino scaffolds attached to quaternary stereocentres is reported. Preliminary investigations revealed a mild base catalysed nucleophilic ring opening of N‐sulfonyl aziridines using the commercially available phosphazene base 2‐tert‐butylimino‐2‐diethylamino‐1,3‐dimethyl‐perhydro‐1

  据报道，一种有效的催化和立体选择性方法可直接构建连接到季立体中心的受保护的乙烯-氨基和丙烯-氨基骨架。初步研究表明，使用市售的磷腈碱2-叔丁基亚氨基-2-二乙氨基-1,3-二甲基-过氢-1,3,2-二氮杂磷（BEMP）可以催化N-磺酰基氮丙啶的轻度碱催化亲核开环。可能并导致与多种次甲基碳酸进行高效烷基化反应。可以使该反应高度不对称（ee高达97％），通过采用相转移催化来控制立体感应。将烷基取代基并入氮丙啶亲电子试剂中，导致该方法具有极高的非对映选择性（高达30：1 dr）。使用N保护的环氨基磺酸盐作为亲电子试剂的进一步扩展成功实现了一系列亲核试剂（高达96％ee和45：1 dr）并允许一系列氮保护基团（氨基甲酸酯，磺酰基，膦酰基，苄基） ）并结合到烷基化加合物中。最后，在有用的杂环和带有天然产物结构成分的化合物的合成中证明了产物的实用性。
• Synthesis of some novel 2-phenylpyridazino[4,5-<i>b</i>][1,5]thiazepines
  作者：Péter Mátyus、Erzsébet Zára-Kaczián、SÁNdor Boros、Zsolt Böcskei

  DOI：10.1002/jhet.5570330309

  日期：1996.5

  Synthesis of some derivatives of the pyridazino[4,5-b][1,5]thiazepine ring system is reported. Thus, 5-benzyl-8-methyl-2-phenyl-2,3.4,5-tetrahydro-5H-pyridazino[4,5-b][1,5]thiazepin-9(8H)-one (5) was prepared by an intramolecular S-alkylation reaction, whereas the thiazepine ring of sulfone analogue 21, and that of the novel tricyclic pyrrolidino fused ring system 22 was elaborated by an intramolecular

  报道了哒嗪并[4，5- b ] [1，5]噻氮平环系统的一些衍生物的合成。因此，5-苄基-8-甲基-2-苯基-2,3.4,5-四氢-5 H-哒嗪[4,5- b ] [1,5]噻嗪酮-9（8 H）-一（5）通过分子内的S-烷基化反应制备了环戊二烯，而通过分子内的C-烷基化反应制备了砜类似物21的硫氮平环和新型三环吡咯烷基稠合环系统22的噻唑烷环。还讨论了双环吡啶并噻嗪稠合的哒嗪系统的意外形成。
• Solid-phase synthesis of arylalkanolamines
  作者：T Srinivasan、P Gupta、B Kundu

  DOI：10.1016/s0040-4039(01)01166-2

  日期：2001.8

  A versatile method for the solid-phase synthesis of differentially substituted arylalkanolamines has been developed using immobilized carbamates. The method has been successfully used for the synthesis of arylethanolamines and arylpropanolamines in high yields and purities.

  使用固定的氨基甲酸酯已开发出一种用于固相合成差异取代的芳基链烷醇胺的通用方法。该方法已成功用于高产率和高纯度的芳基乙醇胺和芳基丙醇胺的合成。