3-(4-bromophenyl)-2-methylpropanal | 246529-83-9

• 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: 3-(4-bromophenyl)-2-methylpropanal
• CAS: 246529-83-9
• 化学式: C₁₀H₁₁BrO
• 分子量: 227.101
• InChiKey: YHTHGACLVZJJBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-2-methylpropanal 在 吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 81.17h， 生成 (R)-methyl 3-(4-bromophenyl)-2-methyl-2-(1-benzyloxycarbonyl-2-(2,2,2-trifluoroacetyl)hydrazinyl)propanoate
  参考文献：
  名称：

  Total Synthesis of LFA-1 Antagonist BIRT-377 via Organocatalytic Asymmetric Construction of a Quaternary Stereocenter

  摘要：

  A catalytic route for enantioselective total synthesis of cell adhesion inhibitor BIRT-377 is described. The quaternary stereocenter was constructed through L-proline-derived, tetrazole-catalyzed direct asymmetric alpha-amination of 3-(4-bromophenyl)-2-methylpropanaI with dibenzyl azodicarboxylate. In the course of these studies, a one-pot trifluoro acetylation/selective benzyloxycarbonyl deprotection method was developed.

  DOI：

  10.1021/ol047368b
• 作为产物：
  描述：

  (E)-3-(4-bromophenyl)-2-methylacrylaldehyde 在 lithium aluminium tetrahydride 、 三氯化铝 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 3-(4-bromophenyl)-2-methylpropanal
  参考文献：
  名称：

  Total Synthesis of LFA-1 Antagonist BIRT-377 via Organocatalytic Asymmetric Construction of a Quaternary Stereocenter

  摘要：

  A catalytic route for enantioselective total synthesis of cell adhesion inhibitor BIRT-377 is described. The quaternary stereocenter was constructed through L-proline-derived, tetrazole-catalyzed direct asymmetric alpha-amination of 3-(4-bromophenyl)-2-methylpropanaI with dibenzyl azodicarboxylate. In the course of these studies, a one-pot trifluoro acetylation/selective benzyloxycarbonyl deprotection method was developed.

  DOI：

  10.1021/ol047368b

文献信息

• Comparative Analysis of the Olfactory Properties of Silicon/Germanium/Tin Analogues of the Lily-of-the-Valley Odorants Lilial and Bourgeonal
  作者：Steffen Dörrich、Lian Gelis、Steffen Wolf、Astrid Sunderkötter、Christoph Mahler、Elena Guschina、Reinhold Tacke、Hanns Hatt、Philip Kraft

  DOI：10.1002/cplu.201402160

  日期：2014.9.18

  The silicon/germanium/tin analogues of the lily‐of‐the‐valley odorants lilial (rac‐1 a), compounds rac‐1 b, rac‐1 c, and rac‐1 d, and bourgeonal (2 a), compounds 2 b, 2 c, and 2 d, were synthesized and characterized for their olfactory properties, including GC–olfactometry studies. Compounds rac‐1 a–c and 2 a–c possess a typical lily‐of‐the‐valley odor, whereas the stanna‐analogues rac‐1 d and 2 d

  百合的最谷气味剂铃兰醛（的硅/锗/锡类似物外消旋- 1），化合物的外消旋- 1b中，外消旋-图1c，和外消旋- 1 d和bourgeonal（2），化合物合成了2 b，2 c和2 d，并对其嗅觉特性进行了表征，包括GC嗅觉研究。化合物外消旋- 1 - c ^和2 - ç具有一个典型的百合的最谷气味，而stanna -类似物外消旋‐ 1 d和2 d，尽管有些花香，但显然不再属于铃兰科。在所研究的两个系列的碳/硅/锗/锡类似物中，铃兰的气味以碳<硅<锗<锡的顺序降低。产生与hOR17-4的稳定四环素调节表达的HEK293细胞系中通过分析重组hOR17-4活化外消旋- 1 - d和2 - d通过使用钙2+成像。Bourgeonal（2）显示出最高的效力激活，而铃兰醛（外消旋- 1）和硅杂bourgeonal（2b的）展示出较低的激活潜能。硅杂铃兰醛（外消旋-图1b），GERMA-铃兰醛（外消旋-
• [EN] SUBSTITUTED AMINO TRIAZOLES, AND METHODS USING SAME<br/>[FR] TRIAZOLES AMINO-SUBSTITUÉS ET PROCÉDÉS D'UTILISATION
  申请人：INST DRUG DELIVERY

  公开号：WO2015095701A1

  公开（公告）日：2015-06-25

  Disclosed are novel substituted amino triazoles of Formula (I), and pharmaceutically acceptable salts thereof. The compounds of Formula (I) are inhibitors of Acidic mammalian chitinase (AMCase) and are useful, in a non-limiting example, for treating asthma. Also provided are pharmaceutical compositions containing at least one compound of the present invention, or a pharmaceutically acceptable salt, hydrate or solvate thereof, and at least one pharmaceutically acceptable carrier, solvent, adjuvant or diluent, and methods of using such compounds and/or compositions to treat asthma and/or to monitor asthma treatment.

  公开了化合物的新型替代氨基三唑的结构，其化学式为（I），以及其药学上可接受的盐。化合物的化学式（I）是酸性哺乳动物几丁质酶（AMCase）的抑制剂，并且在非限制性示例中用于治疗哮喘。还提供了含有本发明至少一种化合物或其药学上可接受的盐、水合物或溶剂化合物的药物组合物，以及至少一种药学上可接受的载体、溶剂、辅料或稀释剂，并使用这些化合物和/或组合物来治疗哮喘和/或监测哮喘治疗的方法。
• Organocatalyzed asymmetric α-hydroxyamination of α-branched aldehydes: asymmetric synthesis of optically active N-protected α,α-disubstituted amino aldehydes and amino alcohols
  作者：Sung-Gon Kim、Tae-Ho Park

  DOI：10.1016/j.tetlet.2006.10.081

  日期：2006.12

  Enantioselective direct α-hydroxyamination and α-aminoxylation of α-branched aldehydes using a proline-derived tetrazole catalyst is described herein. α-Hydroxyamination adducts with up to 90% ee were obtained by the reaction of nitrosobenzene with unactivated α-branched aldehydes under mild reaction conditions.

  本文描述了使用脯氨酸衍生的四唑催化剂对α-支化醛的对映选择性直接α-羟基氨基化和α-氨基羟化。通过亚硝基苯与未活化的α-支化醛在温和的反应条件下反应，可得到ee高达90％的α-羟基化加合物。
• Substituted Pyridopyrazines as Syk Inhibitors
  申请人：HUTCHISON MEDIPHARMA LIMITED

  公开号：US20160002221A1

  公开（公告）日：2016-01-07

  The present invention relates to pyridopyrazine compounds of formula (I), pharmaceutical compositions thereof and methods of use therefore, wherein R 1 , R 2 , R 3 , L, m, p and W are as defined in the specification.

  本发明涉及式(I)的吡啶吡嗪化合物、其制药组合物和使用方法，其中R1、R2、R3、L、m、p和W如规范中所定义。
• Process for the stereoselective synthesis of the E isomer of aryl alkyl oximes
  申请人：RHONE-POULENC INC.

  公开号：EP0009865A1

  公开（公告）日：1980-04-16

  Mixtures of the E and Z isomers of aryl alkyl oximes are converted to 98% or greater E isomer by a process comprising treating a solution of a mixture of E and Z isomers in an organic solvent with a protic or Lewis acid, under anhydrous conditions, to precipitate >98% pure E isomer of an immonium complex and neutralizing the precipitate with an excess of dilute organic/inorganic base, such as Na2CO3 or NaHCO3. The E isomer of the ketoxime is precursor for highly insecticidal ketoximinoethers.

  芳基烷基肟的 E 异构体和 Z 异构体混合物可通过以下工艺转化为 98% 或更高的 E 异构体：在无水条件下，用质酸或路易斯酸处理 E 异构体和 Z 异构体混合物在有机溶剂中的溶液，沉淀出大于 98% 的纯 E 异构体铵络合物，并用过量的稀有机/无机碱（如 Na2CO3 或 NaHCO3）中和沉淀物。酮肟的 E 异构体是高杀虫性酮肟醚的前体。