(8-溴辛基)氨基甲酸叔丁酯 | 142356-35-2

• 物质功能分类: 有机原料 - 氨基化合物 - 无环单胺、多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (8-溴辛基)氨基甲酸叔丁酯
• 英文名称: tert-butyl (8-bromooctyl)carbamate
• 英文别名: tert-butyl N-(8-bromooctyl)carbamate
• CAS: 142356-35-2
• 化学式: C₁₃H₂₆BrNO₂
• 分子量: 308.259
• InChiKey: XBDSVMQPKSQVMH-UHFFFAOYSA-N

物化性质

• 沸点：
  370.2±25.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应存于2-8℃环境中，避免光照，并在惰性气体保护下保存。

制备方法与用途

(8-溴辛基)氨基甲酸叔丁酯可用作有机合成中间体和医药中间体，在实验室研发和化工生产中广泛应用于各种过程。

反应信息

• 作为反应物：
  描述：

  (8-溴辛基)氨基甲酸叔丁酯 在 盐酸 、 sodium hydride 作用下， 以 乙酸乙酯 为溶剂， 反应 25.0h， 生成 2-(S)-<<(benzyloxy)carbonyl>amino>-3-<4-<(8-N-aminooctyl)oxy>phenyl>propionic acid hydrochloride
  参考文献：
  名称：

  Non-Peptide Fibrinogen Receptor Antagonists. 2. Optimization of a Tyrosine Template as a Mimic for Arg-Gly-Asp

  摘要：

  Inhibitors of platelet-fibrinogen binding offer an opportunity to interrupt the final, common pathway for platelet aggregation. Small molecule inhibitors of the platelet fibrinogen receptor GPIIb/IIIa were prepared and evaluated for their ability to prevent platelet aggregation. Compound 23m (L-700,462/MK-383) inhibited in vitro platelet aggregation with an IC50 of 9 nM and demonstrated a selectivity of > 24 000-fold between platelet and human umbilical vein endothelial cell fibrinogen receptors. Dose-dependent inhibition of ex vivo platelet aggregation induced by ADP was achieved with iv infusions of 0.1-10 mu g/kg/min of 23m in anesthetized dogs, with 10 mu g/kg/min completely inhibiting platelet aggregation during the entire 6 h infusion protocol. Platelet aggregatability returned rapidly after the termination of the 23m infusions. These features suggest that 23m may be useful in the treatment of arterial occlusive disorders.

  DOI：

  10.1021/jm00042a007
• 作为产物：
  描述：

  8-叠氮辛烷-1-醇 在 四溴化碳 、 potassium carbonate 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (8-溴辛基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Fluorescent Benzothiazinone Analogues Efficiently and Selectively Label Dpre1 in Mycobacteria and Actinobacteria

  摘要：

  Benzothiazinones (BTZ) are highly potent bactericidal inhibitors of mycobacteria and the lead compound, BTZ043, and the optimized drug candidate, PBTZ169, have potential for the treatment of tuberculosis. Here, we exploited the tractability of the BTZ scaffold by attaching a range of fluorophores to the 2-substituent of the BTZ ring via short linkers. We show by means of fluorescence imaging that the most advanced derivative, JN108, is capable of efficiently labeling its target, the essential flavoenzyme DprE1, both in cell-free extracts and after purification as well as in growing cells of different actinobacterial species. DprE1 displays a polar localization in Mycobacterium tuberculosis, M. marinum, M. smegmatis, and Nocardia farcinica but not in Corynebacterium glutamicum. Finally, mutation of the cysteine residue in DprE1 in these species, to which BTZ covalently binds, abolishes completely the interaction with JN108, thereby highlighting the specificity of this fluorescent probe.

  DOI：

  10.1021/acschembio.8b00790

文献信息

• Chemoselective Synthesis of Lenalidomide-Based PROTAC Library Using Alkylation Reaction
  作者：Xing Qiu、Ning Sun、Ying Kong、Yan Li、Xiaobao Yang、Biao Jiang

  DOI：10.1021/acs.orglett.9b01326

  日期：2019.5.17

  An organic base-promoted chemoselective alkylation of lenalidomide with different halides was developed, which offers a novel approach to a highly functionalized lenalidomide-based PROTAC library under mild reaction conditions. DIPEA was found to act as an efficient base to trigger facile generation of arylamine alkylation products compared with inorganic bases. This library was successfully applied

  开发了一种用不同的卤化物对来那度胺进行有机碱促进的化学选择性烷基化反应，这为在温和的反应条件下以高度功能化来那度胺为基础的PROTAC库提供了一种新颖的方法。与无机碱相比，发现DIPEA是触发芳基胺烷基化产物容易生成的有效碱。该文库已成功应用于BET PROTAC，不仅可以降解BET蛋白，而且还可以有效抑制癌细胞的增殖。
• [EN] HETEROBIFUNCTIONAL COMPOUNDS WITH IMPROVED SPECIFICITYFOR THE BROMODOMAIN OF BRD4<br/>[FR] COMPOSÉS HÉTÉROBIFONCTIONNELS PRÉSENTANT UNE SPÉCIFICITÉ AMÉLIORÉE POUR LE BROMODOMAINE DE BRD4
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2019079701A1

  公开（公告）日：2019-04-25

  Disclosed are heterobifunctional compounds that effectuate selective degradation of a target protein, and which include a targeting ligand that binds a target protein and at least one other protein, a ligand that binds an E3 ubiquitin ligase or a component of E3 ubiquitin ligase, and a specificity modulating linker that links the first ligand and the second ligand. Pharmaceutical compositions containing the compounds, and methods of using and making the compounds are also disclosed.

  本文披露了一种异源双功能化合物，可以实现对目标蛋白的选择性降解。该化合物包括一个结合目标蛋白和至少另一种蛋白的靶向配体，一个结合E3泛素连接酶或E3泛素连接酶组分的配体，以及一个调节特异性的连接子，连接第一配体和第二配体。此外，还披露了含有这些化合物的药物组合物，以及使用和制备这些化合物的方法。
• [EN] BIFUNCTIONAL COMPOUNDS AS CDK MODULATORS<br/>[FR] COMPOSÉS BIFONCTIONNELS AGISSANT PAR AGONISME SUR DES CDK
  申请人：BIOTHERYX INC

  公开号：WO2020023782A1

  公开（公告）日：2020-01-30

  The present application provides compounds of formulae I and II that modulate CDK protein function. Methods of making the compounds, compositions containing the compounds, and the compounds for use in a method of treating or ameliorating of diseases, disorders, or conditions associated with CDK proteins, are also disclosed.

  本申请提供了化合物I和II的公式，这些化合物调节CDK蛋白的功能。还公开了制备这些化合物的方法、含有这些化合物的组合物，以及用于治疗或改善与CDK蛋白相关的疾病、疾病或状况的方法中使用的这些化合物。
• [EN] DEGRADATION OF FAK OR FAK AND ALK BY CONJUGATION OF FAK AND ALK INHIBITORS WITH E3 LIGASE LIGANDS AND METHODS OF USE<br/>[FR] DÉGRADATION DE FAK OU FAK ET ALK PAR CONJUGAISON D'INHIBITEURS DE FAK ET D'ALK AVEC DES LIGANDS DE LIGASE E3 ET PROCÉDÉS D'UTILISATION
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2020069117A1

  公开（公告）日：2020-04-02

  Disclosed are bifunctional compounds (degraders) that target FAK or FAK and ALK for degradation. Also disclosed are pharmaceutical compositions containing the degraders and methods of using the compounds to treat disease.

  揭示了针对FAK或FAK和ALK进行降解的双功能化合物（降解剂）。还揭示了含有这些降解剂的药物组合物以及使用这些化合物治疗疾病的方法。
• Cavitands as Reaction Vessels and Blocking Groups for Selective Reactions in Water
  作者：Daniele Masseroni、Simone Mosca、Matthew P. Mower、Donna G. Blackmond、Julius Rebek

  DOI：10.1002/anie.201602355

  日期：2016.7.11

  The majority of reactions currently performed in the chemical industry take place in organic solvents, compounds that are generally derived from petrochemicals. To promote chemical processes in water, we examined the use of synthetic, deep water‐soluble cavitands in the Staudinger reduction of long‐chain aliphatic diazides (C8, C10, and C12). The diazide substrates are taken up by the cavitand in D2O

  目前在化学工业中进行的大多数反应都是在有机溶剂中进行的，有机溶剂通常是从石油化学产品中衍生出来的。为了促进水中的化学过程，我们研究了在深长链脂肪族二叠氮化物（C 8，C 10和C 12）的斯托丁格还原中使用合成的深水溶性空泡石。叠氮化物底物在D 2中被空泡剂吸收O为折叠的动态构象。一个叠氮化物基团还原为一个胺，得到一种复合物，其中底物以不对称的构象固定，胺端暴露，而叠氮化物端则在空洞内较深且难以接近。因此，即使使用过量的膦，也抑制了第二叠氮化物基团的还原，并且获得了单官能化产物的良好产率。相反，本体溶液中游离重氮化物的还原产生二胺产物。