methyl 4-(2-bromopropanoyl)benzoate | 58764-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(2-bromopropanoyl)benzoate
• 英文别名: α-bromo-p-carbmethoxypropiophenone；4-(2-bromo-propionyl)-benzoic acid methyl ester；methyl 4-(2-bromopropionyl)benzoate
• CAS: 58764-22-0
• 化学式: C₁₁H₁₁BrO₃
• 分子量: 271.111
• InChiKey: LIXAPTRTCGQDGE-UHFFFAOYSA-N

物化性质

• 沸点：
  348.5±22.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  methyl 4-(2-bromopropanoyl)benzoate 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(5-Amino-4-cyano-3-methyl-furan-2-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Acid-mediated Cyclization of 3-Benzoyl-2-cyanobutyronitrile to 2-Amino-4-methyl-5-phenylfuran-3-carbonitrile

  摘要：

  Cyclization of 3-benzoyl-2-cyanobutyronitrile to 2-amino-4-methyl-5-phenylfuran-3-carbonitrile was effected under acidic conditions, rather than the basic conditions previously reported. Since treatment with trifluoroacetic acid (TFA) at room temperature is very mild, 2-amino-4-methyl-5-phenylfuran-3-carbonitriles containing various functional groups can be accessed via this route.

  DOI：

  10.3987/com-03-s(p)13
• 作为产物：
  描述：

  甲基4-丙基苯甲酸酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 methyl 4-(2-bromopropanoyl)benzoate
  参考文献：
  名称：

  NBS和硫脲通过炔烃的一锅法转化2-氨基-4-芳基噻唑

  摘要：

  通过NBS处理，各种烷基芳烃成功地转化为相应的2-氨基-4-芳基噻唑和2,4-二芳基噻唑，然后与硫脲或芳硫代酰胺反应。

  DOI：

  10.1002/ejoc.201900100

文献信息

• Synthesis of Carbamates from Alkyl Bromides and Secondary Amines Using Silver Carbonate
  作者：Vanitha Acharya、Sanjib Mal、Jagadeesh P. Kilaru、Mark G. Montgomery、Sudhindra H. Deshpande、Ravindra P. Sonawane、Bhanu N. Manjunath、Sitaram Pal

  DOI：10.1002/ejoc.201901649

  日期：2020.1.23

  Carbamates were synthesized using silver carbonate as carbonate source. Both symmetric and unsymmetric secondary amines, and a wide range of α‐halopropiophenones were converted into their carbamates.

  使用碳酸银作为碳酸盐源合成氨基甲酸酯。对称和不对称的仲胺，以及各种α-卤代苯乙酮均被转化为氨基甲酸酯。
• [EN] CYSTEINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE CYSTEINE PROTEASE
  申请人：MEDIVIR AB

  公开号：WO2005066180A1

  公开（公告）日：2005-07-21

  A compound of the formula (II) wherein one of R1 and R2 is halo and the other is H or halo; R3 is C1-C4 straight or branched chain, optionally fluorinated, alkyl; R4 is H; or R3 together with R4 and the adjoining backbone carbon defines: a spiro-C5-C7 cycloalkyl, optionally substituted with 1 to 3 substituents selected from halo, hydroxyl, C1-C4 alkyl or C1-C4 haloalkyl; or optionally bridged with a methylene group; or a C4-C6 saturated heterocycle having a hetero atom selected from O, NRa, S, S(=O)2 ; where Ra is H, C1-C4 alkyl or CH3C(=O); R5 is independently selected from H or methyl; E is -C(=O)-, -S(=O)m-, -NR5S(=O)m-, -NR5C(=O)-, -OC(=O)-, R6 is a stable, optionally substituted, monocyclic or bicyclic, carbocycle or hetorocycle; m is independently 0,1 or 2; are inhibitors of cathepsin K and useful in the treatment or prophylaxis of osteoporosis.

  一个公式为(II)的化合物，其中R1和R2中的一个是卤素，另一个是H或卤素；R3是C1-C4直链或支链，可选择氟代的烷基；R4是H；或者R3与R4和相邻的骨架碳一起定义：一个螺环C5-C7环烷基，可选地用1至3个卤素、羟基、C1-C4烷基或C1-C4卤代烷基中的取代基取代；或者可选地用亚甲基桥接；或者是一个具有O、NRa、S、S(=O)2等异原子的C4-C6饱和杂环；其中Ra是H、C1-C4烷基或CH3C(=O)；R5独立地选择自H或甲基；E是-C(=O)-、-S(=O)m-、-NR5S(=O)m-、-NR5C(=O)-、-OC(=O)-；R6是稳定的、可选择取代的、单环或双环的、碳环或杂环；m独立地为0、1或2；是猫hepsin K的抑制剂，并且在骨质疏松症的治疗或预防中有用。
• [EN] PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉASES
  申请人：MEDIVIR AB

  公开号：WO2010034788A1

  公开（公告）日：2010-04-01

  Compounds of the formula II: wherein R1 and R2 are independently H, F or CH3; or R1 forms an ethynyl bond and R2 is H or C3-C6 cycloalkyl which is optionally substituted with one or two substituents independently selected from methyl, CF3, OMe or halo; R3 is C1-C3 alkyl or C3-C6 cycloalkyl, either of which is optionally substituted with one or two methyl and/or a fluoro, trifluoromethyl or methoxy, when R3 is C3-C6 cycloalkyl it may alternatively be gem subsituted with fluoro; R4 is methyl or fluoro; m is 0, 1 or 2; E is a bond, or thiazolyl, optionally substituted with methyl or fluoro; A1 is CH or N, A2 is CR6R7 or NR6, provided at least one Of A1 and A2 comprises N; R6 is H, C1-C4 alkyl, C1-C4 haloalkyl, C1-C3 alkyl-O-C1-C3 alkyl, or when A2 is C, R6 can also be C1-C4 alkoxy or F; R7 is H, C1-C4 alkyl or F or a pharmaceutically acceptable salt, N-oxide or hydrate thereof, have utility in the treatment of disorders characterized by inappropriate expression or activation of cathepsin K, such as osteoporosis, osteoarthritis, rheumatoid arthritis or bone metastases.

  公式II的化合物：其中R1和R2分别为H、F或CH3；或者R1形成乙炔键，R2为H或C3-C6环烷基，可选地被一个或两个从甲基、CF3、OMe或卤素中独立选择的取代基取代；R3为C1-C3烷基或C3-C6环烷基，两者可选地被一个或两个甲基和/或氟、三氟甲基或甲氧基取代，当R3为C3-C6环烷基时，它也可以选择地被氟原子取代；R4为甲基或氟；m为0、1或2；E为键，或噻唑基，可选地被甲基或氟取代；A1为CH或N，A2为CR6R7或NR6，至少其中一个为N；R6为H、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基-C1-C3烷基，或当A2为C时，R6也可以是C1-C4烷氧基或F；R7为H、C1-C4烷基或F或其药学上可接受的盐、N-氧化物或水合物，在治疗由于cathepsin K的不恰当表达或活化而表征的疾病方面具有用途，例如骨质疏松症、骨关节炎、类风湿关节炎或骨转移。
• Cysteine Protease Inhibitors
  申请人：Nilsson Magnus

  公开号：US20090023748A1

  公开（公告）日：2009-01-22

  Compounds of the formula II: wherein R 2 is the side chain of leucine, isoleucine, cyclohexylglycine, O-methyl threonine, 4-fluoroleucine or 3-methoxyvaline; R 3 is H, methyl or F; Rq is trifluoromethyl and Rq′ is H or Rq and Rq′ define keto; Q is a p-(C 1 -C 6 alkylsulphonyl)phenyl- or an optionally substituted 4-(C 1 -C 6 alkyl)piperazin-1-yl-thiazol-4-yl- moiety have utility in the treatment of disorders characterized by inappropriate expression or activation of cathepsin K, such as osteoporosis, osteoarthritis, rheumatoid arthritis or bone metastases.

  II式化合物：其中R2为亮氨酸、异亮氨酸、环己基甘氨酸、O-甲基苏氨酸、4-氟亮氨酸或3-甲氧基缬氨酸的侧链；R3为H、甲基或F；Rq为三氟甲基，Rq′为H或Rq和Rq′定义酮基；Q为p-(C1-C6烷基磺酰基)苯基-或一个可选择取代的4-(C1-C6烷基)哌嗪-1-基噻唑-4-基-部分，用于治疗由于卡托普斯底蛋白K的不当表达或激活而表现出的疾病，例如骨质疏松症、骨关节炎、类风湿性关节炎或骨转移。
• Enantioselective Alkenylation via Nickel-Catalyzed Cross-Coupling with Organozirconium Reagents
  作者：Sha Lou、Gregory C. Fu

  DOI：10.1021/ja1017046

  日期：2010.4.14

  A new family of organometallic compounds, organozirconium reagents, are shown to serve as suitable partners in cross-coupling reactions of (activated) secondary alkyl electrophiles. Thus, the first catalytic method for coupling secondary alpha-bromoketones with alkenylmetal reagents has been developed, specifically, a mild, versatile, and stereoconvergent carbon-carbon bond-forming process that generates

  一个新的有机金属化合物家族，有机锆试剂，被证明可作为（活化的）仲烷基亲电试剂交叉偶联反应的合适伙伴。因此，开发了第一种将仲 α-溴酮与烯基金属试剂偶联的催化方法，特别是一种温和、通用和立体会聚的碳-碳键形成过程，可生成具有良好对映选择性的潜在不稳定 β, γ-不饱和酮。