2-[(E)-1-methoxy-2-phenylethenyl]-5,5-dimethyl-1,3,2-dioxaborinane | 426840-83-7

• 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: 2-[(E)-1-methoxy-2-phenylethenyl]-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 426840-83-7
• 化学式: C₁₄H₁₉BO₃
• 分子量: 246.114
• InChiKey: QZTZQUGUDVWJGP-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(E)-1-methoxy-2-phenylethenyl]-5,5-dimethyl-1,3,2-dioxaborinane 在 bis-triphenylphosphine-palladium(II) chloride 、 Amberlyst 15 、 sodium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 11.0h， 生成 6-phenylacetyl-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of α-Acyl-Functionalized Azacycles by Pd-Catalyzed Cross-Coupling Reactions of α-Alkoxyboronates with Lactam-Derived Vinyl Triflates

  摘要：

  Alkoxydienyl- and alkoxystyrylboronates were used for Pd-catalyzed cross-coupling reactions with lactam-derived vinyl triflates. The hydrolysis of the coupling products with alkoxystyrylboronates provided the corresponding (x-acyl-substituted 3,4-dihydro-(2H)-pyridines and 2,3,4,5-tetrahydroazepines in good to high yields. The hydrolysis of the coupling products with alkoxydienylboronates, performed in the presence of Amberlyst 15, resulted in a Nazarov-type cyclization that afforded hexahydro[1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopenta[b]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds.

  DOI：

  10.1021/jo025930a
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 、 1,1-二甲氧基-2-苯基乙烷 以 甲苯 为溶剂， 生成 2-[(E)-1-methoxy-2-phenylethenyl]-5,5-dimethyl-1,3,2-dioxaborinane
  参考文献：
  名称：

  丁二烯基和苯乙烯基硼酸酯的新合成方法：用于铃木交叉偶联的高反应性中间体。

  摘要：

  烷氧基官能化的丁二烯基和苯乙烯基硼酸酯已从α，β-不饱和缩醛开始合成。这些衍生物易于与芳基底物交联，并且所获得的产物可以在温和的条件下转化为芳族酮，获得与酰化反应相同的结果。[反应：看文字]

  DOI：

  10.1021/ol0255817

文献信息

• N-Functionalization of Azoles through Coupling Reactions with Alkoxydienyl and Alkoxystyryl Boronic Esters
  作者：Annamaria Deagostino、Cristina Prandi、Chiara Zavattaro、Paolo Venturello

  DOI：10.1002/ejoc.200600872

  日期：2007.3

  Alkoxydienyl boronates 1a and 1b and alkoxystyryl boronate 2 have been used in various copper mediated cross-coupling reactions with azoles. A variety of N-alkoxydienyl- and N-styrylazoles have been synthesized under mild conditions. The process utilizes Cu(OAc)2 in the presence of CsF in CH2Cl2 at room temperature. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  烷氧基二烯基硼酸酯 1a 和 1b 和烷氧基苯乙烯基硼酸酯 2 已用于各种铜介导的与唑类的交叉偶联反应。在温和的条件下合成了多种 N-烷氧基二烯基和 N-苯乙烯基唑。该过程在室温下在 CH2Cl2 中 CsF 存在下使用 Cu(OAc)2。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• A New Synthesis of Butadienyl- and Styrylboronic Esters:  Highly Reactive Intermediates for Suzuki Cross-Coupling
  作者：Paolo Balma Tivola、Annamaria Deagostino、Cristina Prandi、Paolo Venturello

  DOI：10.1021/ol0255817

  日期：2002.4.1

  Alkoxy-functionalized butadienyl- and styrylboronic esters have been synthesized starting from alpha,beta-unsaturated acetals. These derivatives readily cross-couple with aryl substrates, and the obtained products can be transformed under mild conditions into aromatic ketones, achieving the same result as an acylation reaction. [reaction: see text]

  烷氧基官能化的丁二烯基和苯乙烯基硼酸酯已从α，β-不饱和缩醛开始合成。这些衍生物易于与芳基底物交联，并且所获得的产物可以在温和的条件下转化为芳族酮，获得与酰化反应相同的结果。[反应：看文字]
• Synthesis of α-Acyl-Functionalized Azacycles by Pd-Catalyzed Cross-Coupling Reactions of α-Alkoxyboronates with Lactam-Derived Vinyl Triflates
  作者：Ernesto G. Occhiato、Cristina Prandi、Alessandro Ferrali、Antonio Guarna、Annamaria Deagostino、Paolo Venturello

  DOI：10.1021/jo025930a

  日期：2002.10.1

  Alkoxydienyl- and alkoxystyrylboronates were used for Pd-catalyzed cross-coupling reactions with lactam-derived vinyl triflates. The hydrolysis of the coupling products with alkoxystyrylboronates provided the corresponding (x-acyl-substituted 3,4-dihydro-(2H)-pyridines and 2,3,4,5-tetrahydroazepines in good to high yields. The hydrolysis of the coupling products with alkoxydienylboronates, performed in the presence of Amberlyst 15, resulted in a Nazarov-type cyclization that afforded hexahydro[1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopenta[b]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds.