(2-丙-1-烯-2-基苯基)硼酸 | 372193-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-丙-1-烯-2-基苯基)硼酸
• 英文名称: (2-(prop-1-en-2-yl)phenyl)boronic acid
• 英文别名: (2-prop-1-en-2-ylphenyl)boronic Acid
• CAS: 372193-54-9
• 化学式: C₉H₁₁BO₂
• 分子量: 161.996
• InChiKey: FPGITLXCVXWCNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  317.8±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-丙-1-烯-2-基苯基)硼酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以92%的产率得到3-bromomethyl-3-methyl-3H-benzo[c][1,2]oxaborol-1-ol
  参考文献：
  名称：

  Bromo-Boronolactonization of Olefins¹

  摘要：

  Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/ H2O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.

  DOI：

  10.1021/jo015838z
• 作为产物：
  描述：

  1-溴-2-丙-1-烯-2-基苯 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(2-丙-1-烯-2-基苯基)硼酸
  参考文献：
  名称：

  Bromo-Boronolactonization of Olefins¹

  摘要：

  Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/ H2O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.

  DOI：

  10.1021/jo015838z

文献信息

• Asymmetric Alkenylation of Enones and Imines Enabled by A Highly Efficient Aryl to Vinyl 1,4-Rhodium Migration
  作者：Shu-Sheng Zhang、Tian-Jiao Hu、Meng-Yao Li、Yi-Kang Song、Xiao-Di Yang、Chen-Guo Feng、Guo-Qiang Lin

  DOI：10.1002/anie.201813585

  日期：2019.3.11

  The asymmetric rhodium‐catalyzed alkenylation of enones and imines with arylboronic acids has been developed. A highly controllable aryl to vinyl 1,4‐rhodium migration is the key step. Stereodefined vinyl moieties were installed in excellent enantioselectivies for most examined examples. DFT calculations reveal that the driving force of this rhodium migration is a kinetically favored process.

  已经开发了烯基和亚胺与芳基硼酸的不对称铑催化的烯基化反应。关键步骤是高度可控制的芳基向乙烯基1,4-铑的迁移。对于大多数检查的实例，将立体定义的乙烯基部分以优异的对映选择性进行安装。DFT计算表明，铑迁移的驱动力是动力学上受青睐的过程。
• Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation of alkenyl- and alkynyl-boronic acids
  作者：Laure Benhamou、Daniel W. Walker、Dejan-Krešimir Bučar、Abil E. Aliev、Tom D. Sheppard

  DOI：10.1039/c6ob01419d

  日期：——

  Two new palladium-catalysed reactions have been developed for the synthesis of stable 4-substituted benzooxaborinin-1-ols. A palladium-catalysed cyclisation of ortho-alkenylbenzene boronic acids can be used to access 4-chlorobenzooxaborinin-1-ols via a Wacker-type oxidation and chlorination. Alternatively, ortho-alkynylbenzene boronic acids undergo a palladium-catalysed oxyallylation reaction to provide

  已经开发出两个新的钯催化的反应，用于合成稳定的4-取代的苯并氧杂卟啉-1-醇。钯催化的邻链烯基苯硼酸的环化反应可用于通过Wacker型氧化和氯化反应获得4-氯苯并氧杂硼酸-1-醇。可替换地，邻位-alkynylbenzene硼酸经历钯催化的反应oxyallylation以提供4- allylbenzooxaborinin -1-醇。
• Selective Synthesis of Phenanthrenes and Dihydrophenanthrenes via Gold-Catalyzed Cycloisomerization of Biphenyl Embedded Trienynes
  作者：Ana Milián、Patricia García-García、Adrián Pérez-Redondo、Roberto Sanz、Juan J. Vaquero、Manuel A. Fernández-Rodríguez

  DOI：10.1021/acs.orglett.0c03067

  日期：2020.11.6

  Readily available o′-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the reaction outcome.

  容易得到O' -烯基- ø -alkynylbiaryls，的1,7-烯炔的特定类型，经历在金（I）催化剂的存在下选择性环异构反应，得到有趣菲和二氢菲衍生物以高产率。所用溶剂在金中间体的生成过程中引起转换，并在反应结果中起关键作用。
• Bromo-Boronolactonization of Olefins¹
  作者：J. R. Falck、Muralidhar Bondlela、Sylesh K. Venkataraman、Dale Srinivas

  DOI：10.1021/jo015838z

  日期：2001.10.1

  Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/ H2O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.