2-[4-(dimethylamino)phenyl]-4,5-dimethyl-1,3,2-dioxaborolane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[4-(dimethylamino)phenyl]-4,5-dimethyl-1,3,2-dioxaborolane
• 英文别名: 4-(4,5-dimethyl-1,3,2-dioxaborolan-2-yl)-N,N-dimethylaniline
• 化学式: C₁₂H₁₈BNO₂
• 分子量: 219.091
• InChiKey: IMMHIRJWFXTYKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[4-(dimethylamino)phenyl]-4,5-dimethyl-1,3,2-dioxaborolane 、 8-acetoxy-Δ¹⁽⁹⁾-octalone-2 在 正丁基锂 、 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以22%的产率得到4,4a,5,6,7,8-六氢-3H-萘-2-酮
  参考文献：
  名称：

  Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates

  摘要：

  In order to find a suitable organometallic compound and a catalyst for the arylation of 8-acetoxyoctalenone 4 (a stereoisomeric mixture of 4 alpha and 4 beta), phenylation was first-investigated with PhZnX (7: X = Cl; 8: X = Br)/Pd or Ni cat., PhSnBu3 (9)/Pd cat. and LiCl, and [PhB(Bu)(OCHMeCHMeO)]Li (10a)/Ni cat. Berate 10a provided the desired product 11a with high stereoselectivity. The stereochemical outcome was irrespective of the stereochemistry of the acetoxy group in 4. Four more aryl groups, p-R-C6H4 (R = Me, MeO, Ph, and Me2N), were installed stereoselectively with this method.

  DOI：

  10.1002/1099-0690(200010)2000:20<3393::aid-ejoc3393>3.0.co;2-c
• 作为产物：
  描述：

  4-二甲基氨基苯硼酸 、 2,3-丁二醇 在 magnesium sulfate 作用下， 以 乙酸乙酯 为溶剂， 以50%的产率得到2-[4-(dimethylamino)phenyl]-4,5-dimethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates

  摘要：

  In order to find a suitable organometallic compound and a catalyst for the arylation of 8-acetoxyoctalenone 4 (a stereoisomeric mixture of 4 alpha and 4 beta), phenylation was first-investigated with PhZnX (7: X = Cl; 8: X = Br)/Pd or Ni cat., PhSnBu3 (9)/Pd cat. and LiCl, and [PhB(Bu)(OCHMeCHMeO)]Li (10a)/Ni cat. Berate 10a provided the desired product 11a with high stereoselectivity. The stereochemical outcome was irrespective of the stereochemistry of the acetoxy group in 4. Four more aryl groups, p-R-C6H4 (R = Me, MeO, Ph, and Me2N), were installed stereoselectively with this method.

  DOI：

  10.1002/1099-0690(200010)2000:20<3393::aid-ejoc3393>3.0.co;2-c

文献信息

• Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates
  作者：Yuichi Kobayashi、Michiko Ito

  DOI：10.1002/1099-0690(200010)2000:20<3393::aid-ejoc3393>3.0.co;2-c

  日期：2000.10

  In order to find a suitable organometallic compound and a catalyst for the arylation of 8-acetoxyoctalenone 4 (a stereoisomeric mixture of 4 alpha and 4 beta), phenylation was first-investigated with PhZnX (7: X = Cl; 8: X = Br)/Pd or Ni cat., PhSnBu3 (9)/Pd cat. and LiCl, and [PhB(Bu)(OCHMeCHMeO)]Li (10a)/Ni cat. Berate 10a provided the desired product 11a with high stereoselectivity. The stereochemical outcome was irrespective of the stereochemistry of the acetoxy group in 4. Four more aryl groups, p-R-C6H4 (R = Me, MeO, Ph, and Me2N), were installed stereoselectively with this method.