isopropyl 4-bromoaceto acetate | 134969-44-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: isopropyl 4-bromoaceto acetate
• 英文别名: isopropyl 4-bromo-3-oxobutanoate；propan-2-yl 4-bromo-3-oxobutanoate
• CAS: 134969-44-1
• 化学式: C₇H₁₁BrO₃
• 分子量: 223.067
• InChiKey: BBSVZBRQVFPVPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl 4-bromoaceto acetate 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 2-(2-Amino-ethoxymethyl)-4-(2,3-dichloro-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-methyl ester
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 9. Structure activity relationships around amlodipine

  摘要：

  The preparation of a range of 1,4-dihydropyridine analogues of amlodipine has been undertaken and their calcium antagonist activities on rat aorta have been evaluated. Increasing the size of the C5 ester group dramatically reduces calcium antagonist activity, a trend which would be compatible with the carbonyl group of that ester binding to the DHP receptor. Amlodipine analogues with extended C3 ester substituents also have lower potency than amlodipine, possibly because of disruption of a favourable interaction between the protonated amino group on the 2-substituent and the DHP receptor. Replacement of the 6-methyl substituent in amlodipine by alkoxyalkyl groups or electron-withdrawing groups is also detrimental to calcium antagonist activity.

  DOI：

  10.1016/0223-5234(91)90132-7
• 作为产物：
  描述：

  溴乙酸异丙酯 在 异丙基溴化镁 作用下， 以 乙醚 为溶剂， 以68%的产率得到isopropyl 4-bromoaceto acetate
  参考文献：
  名称：

  Kel'in, A. V.; Kulinkovich, O. G., Russian Journal of Organic Chemistry, 1994, vol. 30, # 7.2, p. 1129 - 1130

  摘要：

  DOI：

文献信息

• Synthesis of Substituted Alkyl 2H-Pyran-5-carboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1055/s-1997-1400

  日期：1997.6

  The successful synthesis of substituted alkyl 2H-pyran-5-carboxylates 3 from substituted alkyl 3-oxobutanoates 1 and conjugated aldehydes 2 is described.

  成功合成了取代烷基2H-吡喃-5-羧酸酯3，这一过程是通过取代烷基3-氧代丁酸酯1和共轭醛2反应得到的。
• Calcium channel blocking and positive inotropic activities of ethyl 5-cyano-1,4-dihydro-6-methyl-2-[(phenylsulfonyl)methyl]-4-aryl-3-pyridinecarboxylate and analogs. Synthesis and structure-activity relationships
  作者：Ila Sircar、Eva K. Gregor、K. R. Anderson、Stehen J. Haleen、Yu Hsin Shih、Ronald E. Weishaar、Robert P. Steffen、Thomas A. Pugsley、M. D. Taylor

  DOI：10.1021/jm00111a047

  日期：1991.7

  The synthesis and pharmacological evaluation of a series of 2-[(arylsulfonyl)methyl]-4-aryl-5-cyano-1,4-dihydropyridine-3-carboxylic acid esters and analogues are described. These compounds possess a unique profile namely, calcium channel blocking and positive inotropic activities in vitro. Compound 54 was selected as the best compound in the series and was studied in detail. The synthesis and biological

  描述了一系列2-[（（芳基磺酰基）甲基] -4-芳基-5-氰基-1,4-二氢吡啶-3-羧酸酯和类似物的合成和药理学评价。这些化合物具有独特的特性，即钙通道阻滞和体外正性肌力活性。选择化合物54作为该系列中最好的化合物，并进行了详细研究。还报道了54种对映异构体的合成和生物学特征。数据表明，尽管54的钙通道阻滞特性是立体定向的，但正性肌力活性不是。描述和评价了3-和6-氰基和其他紧密相关的1,4-二氢吡啶衍生物的实例以进行比较，发现它们没有上述双重活性。
• Synthesis of Substituted 3(2<i>H</i>)-Furanones Using Alkylative Intramolecular Cyclization of Sulfonium Salts
  作者：Sho Inagaki、Mika Ukaku、Akira Chiba、Fumi Takahashi、Yasuharu Yoshimi、Toshio Morita、Tomikazu Kawano

  DOI：10.1021/acs.joc.6b01528

  日期：2016.9.16

  The facile alkylative intramolecular cyclization of 3-alkoxycarbonyl-2-oxopropyldiphenylsulfonium salts is described. This simple method can be readily applied to the synthesis of a novel family of 4-alkylated 3(2H)-furanones in moderate to high yields under mild conditions via a one-pot process.

  描述了3-烷氧基羰基-2-氧丙基二苯基phenyl盐的容易的烷基化分子内环化。这种简单的方法可以很容易地应用于通过一锅法在温和条件下以中等到高收率合成4-烷基化的3（2 H）-呋喃酮新家族。
• Process for producing optically active 4-halo-3-hydroxybutanoate
  申请人：——

  公开号：US20030134402A1

  公开（公告）日：2003-07-17

  There are provided a polynucleotide sequence coding for an amino acid sequence capable of preferentially producing (S)-4-bromo-3-hydroxy-butanoate by asymmetrically reducing 4-bromo-3-oxobutanoate, A DNA construct having a promoter in operative linkage with the polynucleotide sequence, a recombinant vector containing the polynucleotide sequences a transformant, a recombinant vector and the like.

  提供了一个编码氨基酸序列的多核苷酸序列，能够通过不对称还原4-溴-3-氧代丁酸而优先产生（S）-4-溴-3-羟基丁酸，具有启动子与多核苷酸序列在操作连接的DNA构建物，含有多核苷酸序列的重组载体，一种转化体，一种重组载体等。
• Asymmetric Synthesis of (R)-Nilvadipine and (S)-NB 818 via Regioselective Bromination of Chiral 1,4-Dihydropyridines as a Key Step and Enzymatic Resolution of Racemic 2-Hydroxymethyl-1,4-dihydropyridine Derivatives.
  作者：Hirosato EBIIKE、Kaori MARUYAMA、Yumi OZAWA、Yukiyoshi YAMAZAKI、Kazuo ACHIWA

  DOI：10.1248/cpb.45.869

  日期：——

  Optically active 2-hydroxymethyl-1, 4-dihydropyridines were obtained by lipase-catalyzed hydrolysis or transesterification of racemic materials. Chiral NB 818 and nilvadipine have been synthesized from chiral 2-hydroxymethyl-1, 4-dihydropyridine. On the other hand, chiral 1, 4-dihydropyridines obtained from prochiral substrates have been converted into (S)-NB 818 and (R)-nilvadipine via regioselective bromination of methyl groups under mild conditions.

  通过脂肪酶催化外消旋物质的水解或酯交换反应得到光学活性的2-羟甲基-1,4-二氢吡啶。手性 NB 818 和尼伐地平是由手性 2-羟甲基-1, 4-二氢吡啶合成的。另一方面，从前手性底物获得的手性 1, 4-二氢吡啶在温和条件下通过甲基的区域选择性溴化转化为 (S)-NB 818 和 (R)-尼伐地平。