(2S,3S)-2-(N,N-Dibenzylamino)-3-methylpentanal | 125655-07-4

• 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: (2S,3S)-2-(N,N-Dibenzylamino)-3-methylpentanal
• 英文别名: (2S,3S)-2-(dibenzylamino)-3-methylpentanal
• CAS: 125655-07-4
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: CVEDEXBVZHXRAU-FXAWDEMLSA-N

物化性质

• 沸点：
  386.3±30.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (2S,3S)-2-(N,N-Dibenzylamino)-3-methylpentanal 在 palladium on activated charcoal sodium hydroxide 、 双氧水 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 37.25h， 生成 (4S,5R)-5-[(2S)-butan-2-yl]-4-hydroxypyrrolidin-2-one
  参考文献：
  名称：

  手性硼烯醇盐与手性醛的醛醇加成反应中的试剂控制。（3 S，4 S）-Statine的全合成

  摘要：

  带有薄荷酮的手性配体的硼烯醇盐在与手性醛的反应中能够公平地控制非对映异构。硫醛衍生的（优于酮衍生的）烯醇化物能够控制醛醇的立体化学，而与醛的偏好无关。用硫代乙酸酯衍生的手性烯醇化物和对映体纯的N，N-二苄基α-氨基醛，仅通过改变手性硼配体构型就可以以非常高的非对映选择性获得3，4-抗-或3，4-顺式醇醛加合物。上述步骤用于（3S，4S）-他汀的立体选择性全合成。

  DOI：

  10.1016/s0040-4020(97)00215-9
• 作为产物：
  描述：

  N,N-dibenzyl-L-isoleucine benzyl ester 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 生成 (2S,3S)-2-(N,N-Dibenzylamino)-3-methylpentanal
  参考文献：
  名称：

  Synthesis and identification of unprecedented selective inhibitors of CK1ε

  摘要：

  A small and structure-biased library of enantiopure anti-beta-amino alcohols was prepared in a straightforward manner by a simplified version of the Reetz protocol. Antiproliferative activity testing against a panel of five human solid tumor cell lines gave GI(50) values in the range 1-20 mu M. The reverse screening by computational methods against 58 proteins involved in cancer pointed to kinases as possible therapeutic target candidates. The experimental determination of the interaction with 456 kinases indicated that the compounds behave as selective CK1 epsilon inhibitors. Our results demonstrate that the lead compound represents the first selective CK1 epsilon inhibitor with proven antiproliferative activity in cancer cell lines. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.046

文献信息

• Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates
  作者：Marcin Kaźmierczak、Henryk Koroniak

  DOI：10.3762/bjoc.16.69

  日期：——

  Herein, we present an efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates. Each step of the synthesis was optimized to provide excellent yields. Moreover, the absolute configuration of the obtained compounds was determined by X-ray analysis, which proved the stereochemistry that was proposed based on NMR studies.

  在本文中，我们提出了α-氟化β-氨基膦酸酯的二肽类似物的有效合成。优化了合成的每个步骤，以提供优异的收率。此外，通过X射线分析确定了所得化合物的绝对构型，这证明了基于NMR研究提出的立体化学。
• 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 Arylation of Amino Aldehydes: Overriding Natural Substrate Control through Chelation
  作者：Bruna S. Martins、Angélica V. Moro、Diogo S. Lüdtke

  DOI：10.1021/acs.joc.7b00215

  日期：2017.3.17

  reaction of chiral, enantiopure acyclic α-amino aldehydes enabled by a B/Zn exchange reaction between arylboronic acids and Et2Zn is reported. The presence of dibenzyl substituents at the nitrogen plays a key role in the stereochemical outcome of the reaction, and chelation is favored over the natural tendency of this type of substrate to undergo Felkin–Anh controlled additions with organomagnesium and organolithium

  报道了通过芳基硼酸和Et 2 Zn之间的B / Zn交换反应实现的手性，对映体纯的无环α-氨基醛的螯合控制的芳基化反应。氮上存在的二苄基取代基在反应的立体化学结果中起关键作用，螯合作用优于这种类型的底物通过有机镁和有机锂试剂进行费金-安赫控制的加成反应的自然趋势。
• Zinc-Mediated Allylation of <i>N</i>-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of <i>Anti</i>- and <i>Syn</i>-β-Amino Alcohols with Functionalized Allyl Groups
  作者：Stephen Hanessian、Haeil Park、Rui-Yang Yang

  DOI：10.1055/s-1997-804

  日期：1997.4

  Anti-β-amino alcohols with differently substituted allyl groups were obtained in high chemical yields and in good to excellent diastereoselectivities via Zn-mediated allylation of 2-(dibenzylamino)aldehydes in aqueous media. Swern oxidation, and reduction with NaBH4 gave enantiopure syn-β-amino alcohols in good yields.

  在水中通过锌介导的2-(二苄基氨基)醛的烯丙基化反应，以高化学产率和良好的至优异的非对映选择性获得了具有不同取代烯丙基的抗-β-氨基醇。通过Swern氧化和NaBH4还原，以良好产率得到了高对映纯度的顺-β-氨基醇。
• Synthesis and utilization of trifluoromethylated amino alcohol ligands for the enantioselective Reformatsky reaction and addition of diethylzinc to N-(diphenylphosphinoyl)imine
  作者：Xiu-Hua Xu、Xiao-Long Qiu、Feng-Ling Qing

  DOI：10.1016/j.tet.2008.05.043

  日期：2008.7

  successfully applied in the enantioselective Reformatsky reaction and addition of diethylzinc to N-(diphenylphosphinoyl)imine, respectively. The influence of the substituents on C-3 position and the amino moiety on the enantioselectivity has been carefully investigated. In the best cases, ligand 1b exhibited good selectivity for the enantioselective Reformatsky reaction in 86% ee and ligand 12d provided excellent

  设计并方便地制备了一系列三氟甲基化的氨基醇配体，分别成功地用于对映选择性的Reformatsky反应和将二乙基锌分别添加到N-（二苯基膦酰基）亚胺中。仔细研究了取代基对C-3位和氨基部分对映选择性的影响。在最佳情况下，配体1b对86％ee的对映选择性Reformatsky反应表现出良好的选择性，而配体12d通过向具有95％ee的N-（二苯基膦酰基）亚胺中添加二乙基锌，提供了出色的对映选择性。