benzyl N-(<8-(benzyloxycarbonyl)amino>-4-azaoctyl)carbamate | 89965-56-0

• 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: benzyl N-(<8-(benzyloxycarbonyl)amino>-4-azaoctyl)carbamate
• 英文别名: benzyl N-(8-{[(benzyloxy)carbonyl]amino}-4-azaoctyl)carbamate；benzyl{4-[(3-{[(benzyloxy)carbonyl]amino}propyl)amino]butyl}carbamate；N¹,N¹⁰-bis(benzyloxycarbonyl)spermidine；<3-<<4-(carboxyamino)butyl>amino>propyl>carbamic acid, dibenzyl ester；N¹,N⁸-bis-(phenylmethoxycarbonyl)spermidine；N¹,N¹⁰-di[(benzyloxy)carbonyl]spermidine；N¹,N⁸-bis(benzyloxycarbonyl)spermidine；N¹,N⁸-bis(carbobenzyloxy)spermidine；N¹,N¹⁰-Dicarbobenzoxyspermidine；benzyl N-[3-[4-(benzyloxycarbonylamino)butylamino]propyl]carbamate；benzyl N-[3-[4-(phenylmethoxycarbonylamino)butylamino]propyl]carbamate
• CAS: 89965-56-0
• 化学式: C₂₃H₃₁N₃O₄
• 分子量: 413.517
• InChiKey: AYTWVUUJRQPCGH-UHFFFAOYSA-N

物化性质

• 沸点：
  606.9±55.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-(<8-(benzyloxycarbonyl)amino>-4-azaoctyl)carbamate 在 4-二甲氨基吡啶 、 氢溴酸 、 碳酸氢钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 N4-Succinoyl-N1,N8-bis(N-methyl-N-(benzyloxy)succinamoyl)spermidine
  参考文献：
  名称：

  Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs

  摘要：

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.

  DOI：

  10.1021/jm00122a013
• 作为产物：
  描述：

  N-苄氧羰基-3-氨基丙醛 在 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 5.0h， 生成 benzyl N-(<8-(benzyloxycarbonyl)amino>-4-azaoctyl)carbamate
  参考文献：
  名称：

  Convenient routes to alkyl-substituted polyamines

  摘要：

  DOI：

  10.1016/s0040-4039(00)82421-1

文献信息

• Synthesis of Tenuilobine, a Bis-polyamine Alkaloid fromOncinotis tenuiloba, and Its Transamidation to Isotenuilobine
  作者：Martin K.-H. Doll、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/hlca.19960790221

  日期：1996.3.20

  From the leaves of Oncinotis tenuiloba STAPF, a novel polyamine alkaloid, tenuilobine (9), was isolated. This paper presents the synthesis of 9, as well as the base-catalyzed Zip reaction of 9, leading to the transamidation product isotenuilobine (10). The structure of 10 was further confirmed by 2D-NMR correlation spectroscopy. For analytical purposes, the bis-polyamines 9 and 10 were converted into

  从Oncinotis tenuiloba STAPF的叶子中，分离出一种新型的多胺生物碱tenuilobine（9）。本文介绍了合成的9，以及碱催化邮编的反应9，导致转酰氨产物isotenuilobine（10）。通过2D-NMR相关光谱进一步确认了10的结构。为了分析目的，将双聚胺9和10分别转化为其五乙酰基衍生物12和11，它们可以通过反相HPLC容易地分离。
• Konfiguration und enantioselektive Synthese des Pilzmetaboliten WF14861
  作者：Richard Detterbeck、Manfred Hesse

  DOI：10.1002/hlca.200390015

  日期：2003.1

  A short enantioselective synthesis of the cathepsine inhibitor WF14861 (1) from the funghi Colletotrichum sp. as well as of its diasteroisomer 21 is presented. Comparison of the NMR data of the final products and, in particular, of the [α]D values of the intermediates allowed the confirmation of the formerly proposed structure 1. In addition, the so far unknown absolute configuration of all three stereogenic

  从Funghi Colletotrichum sp。短时对映体合成组织蛋白酶抑制剂WF14861（1）。以及它的非对映异构体21。通过比较最终产物的NMR数据，尤其是中间体的[ α ] D值，可以确认先前提出的结构1。另外，通过该合成可以建立迄今未知的WF14861的所有三个立体异构中心的绝对构型。
• Synthesis of a structural analog of ptilomycalin A
  作者：Anne-Laure Grillot、David J. Hart

  DOI：10.1016/0040-4020(95)00697-7

  日期：1995.10

  Ptilomycalin A analog 2 was prepared by coupling amido alcohol 9 with guanidinium carboxylate 31. The synthesis of 2 requires 13 steps via a longest linear sequence from acrylate 22.

  通过将酰胺醇9与羧酸胍31偶联来制备Ptilomycalin A类似物2。2的合成通过最长的线性顺序由丙烯酸酯22需要13个步骤。
• Stereoselective Synthesisof Novel Ptilomycalin A Analogs via Successive 1,3-Dipolar CycloadditionReactions and their Ca²⁺-ATPase InhibitoryActivity
  作者：Kazuo Nagasawa、Angelina Georgieva、Manabu Hirai、Yuichi Hashimoto、Tadashi Nakata、Yasushi Ohizumi

  DOI：10.1055/s-2003-40195

  日期：——

  The pentacyclic guanidine compounds 4 and 5 were stereoselectively­ synthesized as novel ptilomycalin A and crambescidin analogs. The synthetic method involves successive 1,3-dipolar cycloaddition reactions which effectively access the key intermediates, trans- and cis-2,5-disubstituted pyrrolidine 8 having hydroxyl groups at the β-positions on their side chains. Among the analogs synthesized, 4b and 5b exhibited significant inhibitory activity against Ca2+-ATPase.

  五环胍类化合物4和5被立体选择性合成为新型ptilomycalin A和crambescidin类似物。合成方法涉及连续的1,3-偶极环加成反应，有效获取了关键中间体trans-和cis-2,5-二取代吡咯烷8，它们的侧链在β位具有羟基。在合成的类似物中，4b和5b表现出了显著的Ca2+-ATP酶抑制活性。
• Synthetic Analogues of Naturally Occurring Spider Toxins: Synthesis of 2-(Hydroxyphenyl)propanamides of Spermidine and Spermine
  作者：Kasim Popaj、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/1522-2675(20010418)84:4<797::aid-hlca797>3.0.co;2-2

  日期：2001.4.18

  structure-activity relationships of spider toxins, six model compounds, namely the spermidine derivatives 6, 8, and 16 as well as the spermine derivatives 24, 27, and 32 were synthesized. The synthesis proceeds through stepwise construction of the polyamine backbone, including protection and deprotection of the amino functions. The differentiation of the derivatives by analytical and spectroscopic methods is discussed

  在对蜘蛛毒素构效关系的研究中，合成了六种模型化合物，即亚精胺衍生物 6、8 和 16 以及精胺衍生物 24、27 和 32。合成通过逐步构建多胺骨架进行，包括氨基官能团的保护和去保护。讨论了通过分析和光谱方法对衍生物进行区分。