(S)-2-(N,N-Dibenzylamino)-pentanal | 378752-99-9

• 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: (S)-2-(N,N-Dibenzylamino)-pentanal
• 英文别名: (S)-2-(dibenzylamino)pentanal；(2S)-2-(dibenzylamino)pentanal
• CAS: 378752-99-9
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: XQGBOVZZVRZAPI-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(N,N-Dibenzylamino)-pentanal 在 palladium dihydroxide 盐酸 、 ammonium hydroxide 、 氢气 、 三乙胺 、 calcium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 生成 (4S,5S)-5-Methyl-4-propyl-thiazolidin-2-ylideneamine
  参考文献：
  名称：

  4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.05.031
• 作为产物：
  描述：

  (S)-2-(dibenzylamino)-N-methoxy-N-methylpentanamide 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 (S)-2-(N,N-Dibenzylamino)-pentanal
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF (3S)-3-AMINO-N-CYCLOPROPYL-2-HYDROXYALKANAMIDE DERIVATIVES

  摘要：

  本发明涉及一种制备(2S,3S)-3-氨基-N-环丙基-2-羟基烷酰胺的过程，以及它们在制备HCV抑制剂和卡特普辛抑制剂中的应用。

  公开号：

  US20090234127A1

文献信息

• Antitumoral compounds
  申请人：——

  公开号：US20040048834A1

  公开（公告）日：2004-03-11

  New spisulosine derivatives of use in treating tumors are of the formula (I) wherein: each X is the same or different, and represents H, OH, OR′, SH, SR′, SOR′, SO 2 R′, NO 2 , NH 2 , NHR′, N(R′) 2 , CN, halogen, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups X may together form ═O; Y is NR 1 , OR 1 , PR 1 , SR 1 , or halogen, wherein the number of substituents R 1 is selected to suit the valency and each R 1 is independently selected of H, OH, C(═O)R′, P(═O)R′R″, substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, and wherein the dotted line indicates an optional double bond; each Z is the same different, and represents H, OH, OR′, SH, SR′, SOR′, SO 2 R′, NO 2 , NH 2 , NHR′, N(R′) 2 , NHC(O)R′, CN, halogen, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups Z may together form ═O; z is 0 to 25; y is to 0 to 20; R 2 is H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, S(═O) 2 R′, substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 Alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl; R 3 is H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, S(═O) 2 R′, substituted or unsubstituted C 1 -C 18 alklyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl; each of the R′, R″ groups is independently selected from the group consisting of H, OH, NO 2 , NH 2 , SH, CN, halogen, ═O, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 1 -C 18 alkoxy, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynl, substituted or unsubstituted aryl; there may be one or more unsaturations in the hydrocarbon backbone defined by the chain (II) and salts thereof; with the exception of a C 16 -C 24 2-amino-3-hydroxyalkane or a C 16 -C 24 2-amino-3-hydroxyalkene.

  新的用于治疗肿瘤的斯皮苏林衍生物的化学式为（I），其中：每个X相同或不同，表示H、OH、OR′、SH、SR′、SOR′、SO2R′、NO2、NH2、NHR′、N(R′)2、CN、卤素、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基、取代或未取代的杂芳基，或两个X基团可能共同形成═O；Y为NR1、OR1、PR1、SR1或卤素，其中取代基R1的数量选择以适应化合价，每个R1独立选择自H、OH、C(═O)R′、P(═O)R′R″、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基，虚线表示可选的双键；每个Z相同或不同，表示H、OH、OR′、SH、SR′、SOR′、SO2R′、NO2、NH2、NHR′、N(R′)2、NHC(O)R′、CN、卤素、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基、取代或未取代的杂芳基，或两个Z基团可能共同形成═O；z为0至25；y为0至20；R2为H、C(═O)R′、P(═O)R′R″、S(═O)R′R″、S(═O)2R′、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；R3为H、C(═O)R′、P(═O)R′R″、S(═O)R′R″、S(═O)2R′、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；每个R′、R″基团独立选择自H、OH、NO2、NH2、SH、CN、卤素、═O、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C1-C18烷氧基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；碳链（II）中的碳氢骨架中可能存在一个或多个不饱和度，及其盐；除了C16-C242-氨基-3-羟基烷或C16-C242-氨基-3-羟基烯。
• Stereoselective Synthesis of Trifluoromethylated Vicinal Ethylenediamines with α-Amino <i>N</i>-<i>tert</i>-Butanesulfinimines and TMSCF₃
  作者：G. K. Surya Prakash、Mihirbaran Mandal

  DOI：10.1021/ja020482+

  日期：2002.6.1

  from alpha-amino acids) with Ellman's (R)-N-tert-butanesufinamide without any racemization, and these were trifluoromethylated with TMSCF3 and TMAF (tetramethylammonium fluoride) to the corresponding vicinal ethylenediamines derivatives. Imines derived from l-amino acids gave exclusively one diastereomer with a very high yield.

  可分离的 α-氨基 N-叔丁烷亚胺是通过 Reetz 的 α-氨基醛（由 α-氨基酸制备）与 Ellman (R)-N-叔丁烷亚磺酰胺在没有任何外消旋化的情况下缩合制备的，并且这些用 TMSCF3 和TMAF（四甲基氟化铵）到相应的邻位乙二胺衍生物。源自l-氨基酸的亚胺仅以非常高的产率产生一种非对映异构体。
• [EN] PROCESS FOR THE PREPARATION OF (3S)-3-AMINO-N-CYCLOPROPYL-2-HYDROXYALKANAMIDE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE (3S)-3-AMINO-N-CYCLOPROPYL-2-HYDROXYALCANAMIDE
  申请人：VIROBAY INC

  公开号：WO2009114633A1

  公开（公告）日：2009-09-17

  The present invention relates to a process for the preparation of (2S,3S)-3-amino-N- cyclopropyl-2-hydroxyalkanamides, and their use in the preparation of HCV inhibitors and cathepsin inhibitors.

  本发明涉及一种制备（2S,3S）-3-氨基-N-环丙基-2-羟基脂肪酰胺的方法，以及它们在制备HCV抑制剂和卡特普星抑制剂中的应用。
• Process for the preparation of (3S)-3-amino-N-cyclopropyl-2-hydroxyalkanamide derivatives
  申请人：ViroBay, Inc.

  公开号：US08143448B2

  公开（公告）日：2012-03-27

  The present invention relates to a process for the preparation of (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyalkanamides as well as novel compounds prepared or used in the process.

  本发明涉及一种制备(2S,3S)-3-氨基-N-环丙基-2-羟基烷酰胺的方法，以及在该过程中制备或使用的新化合物。
• KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of <i>N</i>-Sulfinylimines Using HFC-125
  作者：Yuji Sumii、Hiroto Iwasaki、Yamato Fujihira、Elsayed M. Mahmoud、Hiroaki Adachi、Takumi Kagawa、Dominique Cahard、Norio Shibata

  DOI：10.1021/acs.joc.2c01821

  日期：2022.12.2