2-bromo-1-[3,4-methylenedioxyphenyl]ethylene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-bromo-1-[3,4-methylenedioxyphenyl]ethylene
• 英文别名: 5-(2-bromovinyl)benzo[d][1,3]dioxole；3,4-Methylendioxy-bromstyrol；4-(2-Bromvinyl)-1,2-methylendioxy-benzol；5-(2-bromo-vinyl)-benzo[1,3]dioxole；β-bromo-3,4-methylenedioxy-styrene；β-Brom-3,4-methylendioxy-styrol；5-[(1E)-2-bromoethenyl]-2H-1,3-benzodioxole；5-(2-bromoethenyl)-1,3-benzodioxole
• 化学式: C₉H₇BrO₂
• 分子量: 227.057
• InChiKey: SVXOJPBBVAQCRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-1-[3,4-methylenedioxyphenyl]ethylene 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙腈 为溶剂， 以100%的产率得到α-(dibromomethyl)-3,4-methylenedioxybenzenemethanol
  参考文献：
  名称：

  Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation

  摘要：

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.023
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium acetate 、 溶剂黄146 作用下， 生成 2-bromo-1-[3,4-methylenedioxyphenyl]ethylene
  参考文献：
  名称：

  Hoering, Chemische Berichte, 1907, vol. 40, p. 2176

  摘要：

  DOI：

文献信息

• Palladium(0)-Catalyzed Cross-Coupling of 1,1-Diboronates with Vinyl Bromides and 1,1-Dibromoalkenes
  作者：Huan Li、Zhikun Zhang、Xianghang Shangguan、Shan Huang、Jun Chen、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201407000

  日期：2014.10.27

  Palladium‐catalyzed cross‐coupling reactions of 1,1‐diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4‐dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1‐diboronates and allylboron intermediates generated in the initial coupling.

  发现1,1-二硼酸酯与乙烯基溴化物和二溴代烯烃的钯催化交叉偶联反应分别得到1,4-二烯和丙二烯。这些反应利用了在初始偶联过程中产生的1,1-二硼酸酯和烯丙基硼中间体的高反应活性。
• Transition-Metal-Free Iodine Catalyzed Selenocayanation of Styrenyl Bromides and an Easy Access to Benzoselenophenes via Intermediacy of Styrenyl Selenocyanate
  作者：Pintu Maity、Bidisha Paroi、Brindaban C. Ranu

  DOI：10.1021/acs.orglett.7b02571

  日期：2017.11.3

  convenient procedure has been developed for the synthesis of styrenyl selenocyanates and benzoselenophenes from readily available styrenyl bromides by reaction with potassium selenocyanate in the presence of iodine under specified conditions. A series of both compounds have been obtained by this procedure. The synthesis of styrenyl selenocyanates has not been previously reported, and thus this method is of

  已经开发了一种方便的方法，用于在指定条件下，在碘的存在下，通过与硒化氰化钾反应，从易于获得的苯乙烯基溴化物中合成苯乙烯基硒化氰酸酯和苯并硒吩。通过该程序获得了一系列的两种化合物。以前没有报道苯乙烯基硒代氰酸酯的合成，因此该方法具有重要意义。
• Synthesis of 9-Fluorenylidenes via Pd-Catalyzed C–H Vinylation with Vinyl Bromides
  作者：Shuai Yang、Yanghui Zhang

  DOI：10.1021/acs.orglett.1c02722

  日期：2021.10.15

  A facile and efficient approach for the synthesis of 9-fluorenylidenes has been developed via the palladium-catalyzed cross-coupling of 2-iodobiphenyls and vinyl bromides. The reaction involves the C–H activation of 2-iodobiphenyls and dual C–C bond formations. A range of 9-fluorenylidene derivatives, including diphenyldibenzofulvenes, can be synthesized with the reaction.

  通过钯催化的 2-碘联苯和乙烯基溴的交叉偶联，开发了一种简便有效的合成 9-芴基的方法。该反应涉及 2-碘联苯的 C-H 活化和双 C-C 键的形成。通过该反应可以合成一系列 9-芴基衍生物，包括二苯基二苯并富烯。
• Regioselective copper(I)-catalyzed C–H hydroxylation/C–S coupling: expedient construction of 2-(styrylthio)phenols
  作者：Run-Sheng Xu、Lei Yue、Yuan-Jiang Pan

  DOI：10.1016/j.tet.2012.04.048

  日期：2012.6

  Regioselective copper(I)-catalyzed C–H hydroxylation/C–S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the bioactive organic intermediate was also exemplified.

  开发了区域选择性铜（I）催化的芳基硫醇与乙烯基卤化物的CH羟基羟基化/ CS偶联。从取代的芳基硫醇和卤代乙烯开始，可以有效地制备各种2-（苯乙烯基硫代）苯酚衍生物。还举例说明了合成方法用于产生生物活性有机中间体的应用。
• Cooperative <i>N</i>-Heterocyclic Carbene/Palladium-Catalyzed Umpolung 1,4-Addition of Vinyl Bromides to Enals
  作者：Bo Ling、Wenjun Yang、Yan-En Wang、Jianyou Mao

  DOI：10.1021/acs.orglett.0c03654

  日期：2020.12.18

  A highly stereoselective umpolung 1,4-addition of vinyl bromides to enals is enabled by NHC/palladium cooperative catalysis, generating various valuable γ,δ-unsaturated carbonyl derivatives in excellent yields (up to 90%). A detailed mechanism investigation indicates the NHC act as both organocatalyst and ligand for palladium during this system.

  通过NHC /钯协同催化，可以将高度溴化的1,4-乙烯基立体选择性的乙烯基溴加到烯醛上，从而以优异的收率（高达90％）生成各种有价值的γ，δ-不饱和羰基衍生物。详细的机理研究表明，NHC在该系统中既充当有机催化剂又充当钯的配体。