2-bromo-3-methyl-1-butanol | 84984-06-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2-bromo-3-methyl-1-butanol
• 英文别名: 2-Bromo-3-methylbutan-1-ol
• CAS: 84984-06-5
• 化学式: C₅H₁₁BrO
• 分子量: 167.046
• InChiKey: CQNDDHGIVLKUKP-UHFFFAOYSA-N

物化性质

• 沸点：
  85 °C(Press: 12 Torr)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-3-methyl-1-butanol 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 18.0h， 生成 L-缬氨醇
  参考文献：
  名称：

  Asymmetric .ALPHA.-substituted phenethylamines. I. Synthesis of optically pure 1-aryl-N-(2'-hydroxy-1'-isopropylethyl)-2-phenylethylamines.

  摘要：

  通过N-(2-羟基-1-异丙基乙基)苯亚甲基胺(2a-c)与苄基氯化镁的反应，合成了光学纯的1-芳基-N-(2'-羟基-1'-异丙基乙基)-2-苯乙胺(3a-c)。通过N-(2-羟基-1-异丙基乙基)苯乙亚甲基胺(4)与芳基锂化合物的反应，制备了非对映异构体(5a-c)。通过另一条合成路线阐明了3a的光学纯度，并确定了其绝对构型。核磁共振(NMR)谱中特征的甲基信号表明了手性胺(3a-c和5a-c)的构型。

  DOI：

  10.1248/cpb.30.3160
• 作为产物：
  描述：

  2-溴代异戊酸 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 2-bromo-3-methyl-1-butanol
  参考文献：
  名称：

  Asymmetric .ALPHA.-substituted phenethylamines. I. Synthesis of optically pure 1-aryl-N-(2'-hydroxy-1'-isopropylethyl)-2-phenylethylamines.

  摘要：

  通过N-(2-羟基-1-异丙基乙基)苯亚甲基胺(2a-c)与苄基氯化镁的反应，合成了光学纯的1-芳基-N-(2'-羟基-1'-异丙基乙基)-2-苯乙胺(3a-c)。通过N-(2-羟基-1-异丙基乙基)苯乙亚甲基胺(4)与芳基锂化合物的反应，制备了非对映异构体(5a-c)。通过另一条合成路线阐明了3a的光学纯度，并确定了其绝对构型。核磁共振(NMR)谱中特征的甲基信号表明了手性胺(3a-c和5a-c)的构型。

  DOI：

  10.1248/cpb.30.3160

文献信息

• [EN] 5-ALKYLTHIO-7-[(4-ARYLBENZYL)AMINO]-1(2)H-PYRAZOLO[4,3-D]PYRIMIDINES FOR TREATMENT OF LYMPHOMA<br/>[FR] 5-ALKYLTHIO-7-[(4-ARYLBENZYL) AMINO] -1 (2) H-PYRAZOLO [4,3-D] PYRIMIDINES POUR LE TRAITEMENT DU LYMPHOME
  申请人：UNIV PALACKEHO

  公开号：WO2019149295A1

  公开（公告）日：2019-08-08

  The present invention relates to 5-alkylthio-7-[(4-arylbenzyl)amino]-1(2)H-pyrazolo[4,3-d]pyrimidine derivatives of formula I which are effective inhibitors of kinases and exhibit strong antiproliferative and proapoptotic properties on lymphoma cells. This invention further relates to use of said derivatives in the treatment of blood hyperproliferative diseases, such as Non-Hodgkin lymphomas.

  本发明涉及式I的5-烷基硫基-7-[(4-芳基苄基)氨基]-1(2)H-吡唑并[4,3-d]嘧啶衍生物，它们是激酶的有效抑制剂，并在淋巴瘤细胞上表现出强烈的抗增殖和促凋亡特性。本发明还涉及利用这些衍生物治疗血液过度增殖性疾病，如非霍奇金淋巴瘤。
• Organocatalytic Enantioselective α-Bromination of Aldehydes with <i>N</i>-Bromosuccinimide
  作者：George Hutchinson、Carla Alamillo-Ferrer、Martín Fernández-Pascual、Jordi Burés

  DOI：10.1021/acs.joc.2c00600

  日期：2022.6.17

  four examples reported to date require expensive, inconvenient brominating agents to achieve the desired products in excellent yields and enantioselectivities. The preferred brominating agent, N-bromosuccinimide (NBS), has been repeatedly discarded for these reactions because it results in low yields and relatively poor enantioselectivities. We describe a methodology that uses NBS and performs excellently

  尽管存在大量的有机催化、对映选择性转化，但醛的 α-溴化仍然是一个具有挑战性的反应。迄今为止报道的四个例子需要昂​​贵且不方便的溴化剂才能以优异的收率和对映选择性获得所需的产品。优选的溴化剂N-溴代琥珀酰亚胺 (NBS) 已在这些反应中反复丢弃，因为它导致低产率和相对较差的对映选择性。我们描述了一种使用 NBS 并在低催化剂负载、短反应时间和温和温度下表现出色的方法。
• Salmon-Legagneur; Neveu, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 2217
  作者：Salmon-Legagneur、Neveu

  DOI：——

  日期：——
• 3,5,7-Substituted Pyrazolo[4,3-<i>d</i>]pyrimidine Inhibitors of Cyclin-Dependent Kinases and Their Evaluation in Lymphoma Models
  作者：Radek Jorda、Libor Havlíček、Antonín Šturc、Diana Tušková、Lenka Daumová、Mahmudul Alam、Jana Škerlová、Michaela Nekardová、Miroslav Peřina、Tomáš Pospíšil、Jitka Široká、Lubor Urbánek、Petr Pachl、Pavlína Řezáčová、Miroslav Strnad、Pavel Klener、Vladimír Kryštof

  DOI：10.1021/acs.jmedchem.9b00189

  日期：2019.5.9

  Cyclin-dependent kinases are therapeutic targets frequently deregulated in various cancers. By convenient alkylation of the 5-sulfanyl group, we synthesized 3-isopropyl-7-[4-(2-pyridyl)benzyl]amino-1(2)H-pyrazolo[4,3-d]pyrimidines with various substitutions at position 5 with potent antiproliferative activity in non-Hodgkin lymphoma cell lines. The most potent derivative 4.35 also displayed activities across more than 60 cancer cell lines. The kinase profiling confirmed high selectivity of 4.35 toward cyclin-dependent kinases (CDKs) 2, 5, and 9, and the cocrystal with CDK2/cyclin A2 revealed its binding in the active site. Cultured lymphoma cell lines treated with 4.35 showed dephosphorylation of CDK substrates, cleavage of PARP-1, downregulation of XIAP and MCL-1, and activation of caspases, which collectively confirmed ongoing apoptosis. Moreover, 4.35 demonstrated significant activity in various cell line xenograft and patient-derived xenograft mouse models in vivo both as a monotherapy and as a combination therapy with the BCL2-targeting venetoclax. These findings support further studies of combinatorial treatment based on CDK inhibitors.
• Stereocontrol in radical cyclizations on sugar templates
  作者：Catherine Lesueur、Robert Nouguier、Michéle Paula Bertrand、Pascale Hoffmann、Alain De Mesmaeker

  DOI：10.1016/s0040-4020(01)80694-3

  日期：1994.5

  The radical cyclization of alkyl hex-2-enopyranosides provides a stereocontrolled route to fused furanopyranes. The intermediate radical is generated either via the reduction of the appropriate halide by tin hydride or via sulfonyl radical addition to allyl hex-2-enopyranosides. The two methodologies are compared with respect to diastereoselectivity. Stereocontrol is discussed on the basis of conformational preference in the transition state.