2-(Boc-氨基)-3-丁醇 | 169324-82-7

• 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: 2-(Boc-氨基)-3-丁醇
• 中文别名: N-[1-(羟甲基)-2-丙烯-1-基]-氨基甲酸叔丁基酯；2-(BOC-氨基)-3-丁醇；2-(BOC-氨基)-3-丁烯-1-醇
• 英文名称: 2-tert-butoxycarbonylamino-3-buten-1-ol
• 英文别名: 2-(N-tert-butoxycarbonylamino)-3-buten-1-ol；N-tert-butoxycarbonyl-N-(1-hydroxymethyl-2-propenyl)amine；(rac)-N-Boc-vinylglycinol；(1-hydroxymethylallyl)carbamic acid tert-butyl ester；2-(Boc-amino)-3-buten-1-ol；tert-butyl N-(1-hydroxybut-3-en-2-yl)carbamate
• CAS: 169324-82-7
• 化学式: C₉H₁₇NO₃
• mdl: MFCD06797560
• 分子量: 187.239
• InChiKey: HYVYNSIWYIWTCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  2-(Boc-氨基)-3-丁醇 在 [RuCl₂(=CHPh)PCy₃)2] potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 26.33h， 生成 [(2S)-1-(4-bromophenyl)sulfonyl-4-[(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-(2-nitrophenyl)sulfonyl-3,6-dihydro-2H-pyridin-5-yl]-2,5-dihydropyrrol-2-yl]methyl benzoate
  参考文献：
  名称：

  An Oligomer-Based Approach to Skeletal Diversity in Small-Molecule Synthesis

  摘要：

  Access to small molecules of widely varying molecular shapes has been identified as an enabling step in the discovery of biologically active materials. In this communication we introduce an approach to the systematic development of architecturally distinct chemical compounds based upon the assembly of reactive monomers into linear oligomers, each of which encodes a unique molecular framework under a common set of reaction conditions. Certain products of the initial chemical transformation (Ru-catalyzed metathesis reaction) encode additional skeletons upon treatment with a second common set of reagents (Diels-Alder dienophiles). Application of this oligomerization approach has led to the discovery of a previously unreported tandem ene-yne-yne metathesis-6pi-electrocyclization-1,5-hydride migration that converts a linear substrate into a complex tricyclic 1,3-diene in a single step. Thus, the reported strategy might serve not only as a generator of skeletally diverse small molecules but also as a discovery platform for the identification of novel chemical transformations.

  DOI：

  10.1021/ja065724a
• 作为产物：
  描述：

  N-重氮基氨基甲酸叔-丁基酯 在 偶氮二异丁腈 、 三正丁基氢锡 、 iron(II) chloride 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 2-(Boc-氨基)-3-丁醇
  参考文献：
  名称：

  Fe(II)-Catalyzed Imidation of Allyl Sulfides and Subsequent [2,3]-Sigmatropic Rearrangement. Preparation of α-Branched N-tert-Butyloxycarbonyl (Boc)-Protected N-Allylamines

  摘要：

  Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2,3]-sigmatropic rearrangement reaction upon treatment with N-tert-butyloxycarbonyl azide (BocN(3)) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75% (12 examples), Whereas the reaction is well suited for the transformation of alpha-unbranched sulfides to a-branched sulfenamides, the enantiomerically pure alpha-branched sulfides 10 and 13 reacted sluggishly. The corresponding sulfenamides 22 and 23 were obtained in only moderate enantiomeric excess (36-39% eel. A reaction mechanism is proposed that postulates the intermediacy of an N-Boc-substituted Fe(IV)-nitrene complex 14 acting as the imidation reagent in the catalytic cycle. Possible side reactions are discussed. The benzenesulfenamides 3 were further converted into N-Boc-N-allylamines 4 by removal of the phenylsulfanyl group. Bu3SnH in benzene was found to be the reagent of choice for the deprotection of alpha-branched amines that bear a secondary allyl substituent (five examples, 71-93% yield). This method failed for the alpha-branched amines 3i-k with a tertiary allyl substituent. The phenylsulfanyl group was finally removed with P(OEt)(3)/NEt3 in CH2Cl2 (three examples, 43-62% yield).

  DOI：

  10.1021/jo991569p

文献信息

• 2-(3-Pyrrolin-1-yl)-1,4-naphthoquinones: Photoactivated Alkylating Agents
  作者：Aaron Aponick、Amber L. Dietz、William H. Pearson

  DOI：10.1002/ejoc.200800482

  日期：2008.9

  The preparation of 2-(3-pyrrolin-1-yl)-1,4-naphthoquinones and a study of their use as photoactivated alkylating agents is reported. The title compounds were easily synthesized by conjugate addition of the corresponding 3-pyrrolines to various naphthoquinones. Upon exposure to ambient room light, the compounds undergo an internal redox reaction to form 2-(pyrrol-1-yl)-1,4-hydroquinones, which are activated

  报道了 2-(3-pyrrolin-1-yl)-1,4-naphthoquinones 的制备及其作为光活化烷化剂的用途。通过将相应的 3-吡咯啉与各种萘醌进行共轭加成，很容易合成标题化合物。暴露于环境室内光线后，这些化合物会发生内部氧化还原反应，形成 2-(pyrrol-1-yl)-1,4-hydroquinone，其被活化为
• Imidazopyrazines as protein kinase inhibitors
  申请人：Zhao Lianyun

  公开号：US20070117804A1

  公开（公告）日：2007-05-24

  In its many embodiments, the present invention provides a novel class of imidazopyrazine compounds as inhibitors of protein and/or checkpoint kinases, methods of preparing such compounds, pharmaceutical compositions including one or more such compounds, methods of preparing pharmaceutical formulations including one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the protein or checkpoint kinases using such compounds or pharmaceutical compositions.

  本发明的多种实施例提供了一类新型的咪唑吡嗪化合物，作为蛋白质和/或检查点激酶的抑制剂，包括制备这类化合物的方法、包含一个或多个这类化合物的药物组合物、制备包含一个或多个这类化合物的药物制剂的方法，以及使用这类化合物或药物组合物治疗、预防、抑制或改善与蛋白质或检查点激酶相关的一个或多个疾病的方法。
• Synthesis of Unnatural Amino Acids via Suzuki Cross-Coupling of Enantiopure Vinyloxazolidine Derivatives
  作者：Mark Sabat、Carl R. Johnson

  DOI：10.1021/ol005645i

  日期：2000.4.1

  S)-alpha-Amino alcohols and alpha-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal

  通过钯催化的交叉偶联Suzuki反应合成了（R和S）-α-氨基醇和α-氨基酸，包括4-甲氧基高苯丙氨酸，并带有各种非天然的侧链。由常见的非手性前体2-丁烯-1,4-二醇合成的关键结构单元1和2，利用假单胞菌洋葱脂肪酶催化的动力学拆分，制成对映体纯净的。描述了铃木交叉偶联和随后氧化所得α-氨基醇的最佳条件。
• Discovery of 4,7-Diamino-5-(4-phenoxyphenyl)-6-methylene-pyrimido[5,4-<i>b</i>]pyrrolizines as Novel Bruton’s Tyrosine Kinase Inhibitors
  作者：Yu Xue、Peiran Song、Zilan Song、Aoli Wang、Linjiang Tong、Meiyu Geng、Jian Ding、Qingsong Liu、Liping Sun、Hua Xie、Ao Zhang

  DOI：10.1021/acs.jmedchem.8b00441

  日期：2018.5.24

  An alternative medicinal chemistry approach was conducted on Bruton’s tyrosine kinase (BTK) inhibitor 1 (ibrutinib) by merging the pyrazolo[3,4-d]pyrimidine component into a tricyclic skeleton. Two types of compounds were prepared, and their biochemical activities on BTK as well as stereochemistry effects were determined. Structural optimization focusing on the reactive binding group to BTK Cys481

  通过将吡唑并[3,4- d ]嘧啶组分合并成三环骨架，对布鲁顿酪氨酸激酶（BTK）抑制剂1（依鲁替尼）进行了另一种药物化学处理。制备了两种类型的化合物，并确定了它们对BTK的生化活性以及立体化学作用。进行了结构优化，重点是与BTK Cys481的反应性结合基团和以代谢研究为指导的代谢位点。7S被认为是最有效的，对BTK的IC 50值为0.4 nM，对BTK依赖的TMD8细胞的IC 50为16 nM。相比1，7S对B细胞受体信号通路的抑制作用强一些。在源自TMD8细胞的动物异种移植模型中，7S在15 mg / kg QD剂量下显示出5.3的相对肿瘤体积，在25 mg / kg QD较高剂量下比1（RTV 6.6）更有效。所有这些结果表明7S是一种值得进一步分析的新型BTK抑制剂。
• Methods for inhibiting protein kinases
  申请人：Guzi J. Timothy

  公开号：US20070105864A1

  公开（公告）日：2007-05-10

  The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim-1 kinase, and tyrosine kinase using imidazo[1,2-a]pyrazine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.

  本发明提供了利用咪唑并[1,2-a]吡嗪化合物抑制来自AKT、检查点激酶、枢纽激酶、Pim-1激酶和酪氨酸激酶的蛋白激酶的方法，以及利用这些化合物治疗、预防、抑制或改善与蛋白激酶相关的一种或多种疾病的方法。