3-(bromomethyl)isobenzofuran-1(3H)-one | 180404-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(bromomethyl)isobenzofuran-1(3H)-one
• 英文别名: Brommethylphthalid；3-(bromomethyl)-3H-2-benzofuran-1-one
• CAS: 180404-69-7
• 化学式: C₉H₇BrO₂
• 分子量: 227.057
• InChiKey: BODPQCJKIOOFMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙烯基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 三苯基瞵硫 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-(bromomethyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids

  摘要：

  A facile and enantioselective approach toward 3,4-dihydroisocoumarin was developed. The method involved an amino-thiocarbamate catalyzed enantioselective bromocyclization of styrene-type carboxylic acids, yielding 3-bromo-3,4-dihydroisocoumarins with good yields and ee's. 3-Bromo-3,4-dihydroisocoumarins are versatile building blocks for various dihydroisocoumarin derivatives in which the Br group can readily be modified to achieve biologically important 4-O-type and 4-N-type 3,4-dihydroisocoumarin systems. In addition, studies indicated that, by refining some parameters, the synthetically useful 5-exo phthalide products could be achieved with good yields and ee's.

  DOI：

  10.1021/jo202221c

文献信息

• [EN] DERIVATIVES OF UNCIALAMYCIN, METHODS OF SYNTHESIS AND THEIR USE AS ANTITUMOR AGENTS<br/>[FR] DÉRIVÉS DE L'UNCIALAMYCINE, PROCÉDÉS DE SYNTHÈSE ET LEUR UTILISATION COMME AGENTS ANTI-TUMORAUX
  申请人：UNIV RICE WILLIAM M

  公开号：WO2015023879A1

  公开（公告）日：2015-02-19

  In one aspect, the present disclosure provides new analogs of uncialamycin of formulae (I) and (II). The present disclosure also provides novel synthetic pathways to obtaining uncialamycin and analogs thereof. Additionally, the present disclosure also describes methods of use of uncialamycin and analogs thereof. In another aspect, the present disclosure provides antibody-drug conjugates comprising the compounds of formulae (I) and (ll).

  在一方面，本公开提供了一种新的草酸霉素类似物，其公式为(I)和(II)。本公开还提供了获得草酸霉素及其类似物的新合成途径。另外，本公开还描述了使用草酸霉素及其类似物的方法。在另一方面，本公开提供了包含公式(I)和(II)化合物的抗体-药物偶联物。
• Electrochemical bromofunctionalization of alkenes in a flow reactor
  作者：Jakob Seitz、Thomas Wirth

  DOI：10.1039/d1ob01302e

  日期：——

  of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, the in situ generation of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted

  迄今为止，有机分子的溴化已得到广泛研究，但仍然需要安全和可持续的方法。有害试剂、选择性、低原子经济性和废物产生是溴化试剂最持久的问题。溴化物电化学氧化成溴是通过避免化学氧化剂减少废物的可行策略。此外，活性中间体的原位生成将危险试剂的风险降至最低。在这项工作中，我们研究了在流动电化学反应器中从氢溴酸电化学生成溴。各种烯烃可以以良好到极好的收率转化为其相应的二溴化物、溴醇、溴醇醚和环化产物。
• Addition and in situ halo-cyclization of ω-alkenyl Grignard reagents with aldehydes, ketones, carbon dioxide, and azodicarboxylate
  作者：Yasutomo Yamamoto、Misa Shimizu、Ai Ohara、Akari Miyawaki、Kiyoshi Tomioka

  DOI：10.1039/c3nj00765k

  日期：——

  An addition reaction of ω-alkenylmagnesium bromide with aldehydes and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated tetrahydrofuran in one pot. The reaction was also applicable to a one-pot synthesis of 2,5,5-trisubstituted tetrahydrofuran, lactone, and pyrazolidine using a ketone, carbon dioxide, and azodicarboxylate, respectively, as electrophiles. One-pot iodo-

  ω-烯基溴化镁与醛的加成反应和与碘代苯二乙酸的连续氧化环化反应在一个锅中得到溴化四氢呋喃。该反应还适用于分别使用酮，二氧化碳和偶氮二羧酸酯作为亲电子试剂的一锅合成2,5,5-三取代四氢呋喃，内酯和吡唑烷。用烯基碘化镁和氯化物也可以一锅碘和氯环化。
• DERIVATIVES OF UNCIALAMYCIN, METHODS OF SYNTHESIS AND THEIR USE AS ANTITUMOR AGENTS
  申请人：WILLIAM MARSH RICE UNIVERSITY

  公开号：US20160185791A1

  公开（公告）日：2016-06-30

  In one aspect, the present disclosure provides new analogs of uncialamycin of formulae (I) and (II). The present disclosure also provides novel synthetic pathways to obtaining uncialamycin and analogs thereof. Additionally, the present disclosure also describes methods of use of uncialamycin and analogs thereof. In another aspect, the present disclosure provides antibody-drug conjugates comprising the compounds of formulae (I) and (II).

  在某个方面，本公开提供了式（I）和（II）的新的uncialamycin类似物。本公开还提供了获得uncialamycin及其类似物的新型合成途径。此外，本公开还描述了uncialamycin及其类似物的使用方法。在另一方面，本公开提供了包含式（I）和（II）化合物的抗体药物偶联物。
• Derivatives of uncialamycin, methods of synthesis and their use as antitumor agents
  申请人：WILLIAM MARSH RICE UNIVERSITY

  公开号：US10233192B2

  公开（公告）日：2019-03-19

  In one aspect, the present disclosure provides new analogs of uncialamycin. The present disclosure also provides novel synthetic pathways to obtaining uncialamycin and analogs thereof. Additionally, the present disclosure also describes methods of use of uncialamycin and analogs thereof. In another aspect, the present disclosure provides antibody-drug conjugates which may be used to treat cancer or another disease or disorder.

  一方面，本公开提供了新的安卡拉霉素类似物。本公开还提供了获得安卡拉霉素及其类似物的新合成途径。此外，本公开还描述了使用安卡拉霉素及其类似物的方法。在另一方面，本公开提供了可用于治疗癌症或其他疾病或紊乱的抗体-药物共轭物。