1-(3-bromophenyl)ethane-1,2-diyl diacetate | 1219705-99-3

• 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: 1-(3-bromophenyl)ethane-1,2-diyl diacetate
• 英文别名: [2-Acetyloxy-2-(3-bromophenyl)ethyl] acetate
• CAS: 1219705-99-3
• 化学式: C₁₂H₁₃BrO₄
• 分子量: 301.137
• InChiKey: SSFXLSUQWKIIHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  碘苯二乙酸 、 3-溴苯乙烯 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 16.0h， 以79%的产率得到1-(3-bromophenyl)ethane-1,2-diyl diacetate
  参考文献：
  名称：

  Copper-Catalyzed Diacetoxylation of Olefins using PhI(OAc)₂ as Oxidant

  摘要：

  Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions, The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds in 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.

  DOI：

  10.1021/ol902813m

文献信息

• 1-Fluoro-1-sulfonyloxylation of Alkenes by Sterically and Electronically Tuned Hypervalent Iodine: Regression Analysis toward 1,1-Heterodifunctionalization
  作者：Masaki Fujie、Kyohei Mizufune、Yoshihiro Nishimoto、Makoto Yasuda

  DOI：10.1021/acs.orglett.2c04235

  日期：2023.2.10

  the heterodifunctionalization of alkenes, 1,1-regioselectivity remains elusive in sharp contrast to 1,2-regioselectivity. Herein, the 1-fluoro-1-sulfonyloxylation of styrenes with Bu4NBF4 and sulfonic acids using a hypervalent iodine ArI(OAc)2 is reported. Regression analysis of substituents on ArI(OAc)2 suggested that their electron-withdrawing ability and steric factor influence the 1,1-heterodifunctionalization

  在烯烃的异双功能化中，1,1-区域选择性与 1,2-区域选择性形成鲜明对比，仍然难以捉摸。在此，报道了使用高价碘 ArI(OAc) 2对苯乙烯与 Bu 4 NBF 4和磺酸进行1-氟-1-磺酰氧基化反应。ArI(OAc) 2上取代基的回归分析表明它们的吸电子能力和空间因素影响1,1-异双功能化。我们设计了o -2,4-(CF 3 ) 2 C 6 H 3 }-和p -NO 2 -取代的ArI(OAc) 2通过回归分析实现高选择性。
• B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant
  作者：Jiuzhong Huang、Lu Ouyang、Jianxiao Li、Jia Zheng、Wuxin Yan、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.8b01806

  日期：2018.9.7

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.