2-(Bromomethyl)-1,3-bis[2,6-di(propan-2-yl)phenyl]benzene | 895146-09-5

• 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-(Bromomethyl)-1,3-bis[2,6-di(propan-2-yl)phenyl]benzene
• 英文别名: 2-(bromomethyl)-1,3-bis[2,6-di(propan-2-yl)phenyl]benzene
• CAS: 895146-09-5
• 化学式: C₃₁H₃₉Br
• 分子量: 491.555
• InChiKey: OLWFRJDTQULKJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(Bromomethyl)-1,3-bis[2,6-di(propan-2-yl)phenyl]benzene 、 甲酸 以 四氢呋喃 为溶剂， 以88%的产率得到[2,6-Bis[2,6-di(propan-2-yl)phenyl]phenyl]methyl formate
  参考文献：
  名称：

  ipso-and para-Functionalization of meta-terphenyl ligands with substituted methyl groups: Unusual head-to-tail coupling of terphenyl moieties

  摘要：

  The synthesis and characterization of several ipso-functionalized derivatives of the bulky terphenyl group C6H3-2,6(C6H3-2',6'-Pr-2(i))(2)(Ar') are described. These include the primary alcohol Ar'CH2OH (1), the bromo derivative Ar'CH2Br (2), and the terphenyl formate Ar'CH2OC(O)H (3). The alcohol 1 was obtained by treatment of LiAr' with formaldehyde, and 1 was readily converted to the bromo derivative 2 using HBr. The reaction of 1 with formic acid afforded 3 in good yield. Attempts to form the Grignard derivative of 1, i.e., Ar'CH2MgBr, resulted in a head-to-tail reaction of the terphenyl benzyl units to yield an unusual coupled product 4. An approach to the avoidance of this coupling involved the synthesis of the terphenyl derivatives 1-I-C6H2-2,6(C6H3-2',6'-Pr-2(i))(2)-4-Me (5) and 1-I-C6H2-2,6(C6H2-2',4',6'-Pr-3(i))(2)-4-Me (6), bearing methyl groups in the para positions of the central aryl ring, which could be prepared in good yield, and converted to their respective lithium salts 7 and 8 without complication. The compounds were characterized by H-1 and C-13 NMR spectroscopy, IR spectroscopy (1) and X-ray crystallography (2, 4, 5 and 6). (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.01.047
• 作为产物：
  描述：

  2,6-bis(2,6-diisopropylphenyl)benzyl alcohol 在 氢溴酸 作用下， 反应 3.0h， 以96%的产率得到2-(Bromomethyl)-1,3-bis[2,6-di(propan-2-yl)phenyl]benzene
  参考文献：
  名称：

  ipso-and para-Functionalization of meta-terphenyl ligands with substituted methyl groups: Unusual head-to-tail coupling of terphenyl moieties

  摘要：

  The synthesis and characterization of several ipso-functionalized derivatives of the bulky terphenyl group C6H3-2,6(C6H3-2',6'-Pr-2(i))(2)(Ar') are described. These include the primary alcohol Ar'CH2OH (1), the bromo derivative Ar'CH2Br (2), and the terphenyl formate Ar'CH2OC(O)H (3). The alcohol 1 was obtained by treatment of LiAr' with formaldehyde, and 1 was readily converted to the bromo derivative 2 using HBr. The reaction of 1 with formic acid afforded 3 in good yield. Attempts to form the Grignard derivative of 1, i.e., Ar'CH2MgBr, resulted in a head-to-tail reaction of the terphenyl benzyl units to yield an unusual coupled product 4. An approach to the avoidance of this coupling involved the synthesis of the terphenyl derivatives 1-I-C6H2-2,6(C6H3-2',6'-Pr-2(i))(2)-4-Me (5) and 1-I-C6H2-2,6(C6H2-2',4',6'-Pr-3(i))(2)-4-Me (6), bearing methyl groups in the para positions of the central aryl ring, which could be prepared in good yield, and converted to their respective lithium salts 7 and 8 without complication. The compounds were characterized by H-1 and C-13 NMR spectroscopy, IR spectroscopy (1) and X-ray crystallography (2, 4, 5 and 6). (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.01.047

文献信息

• ipso-and para-Functionalization of meta-terphenyl ligands with substituted methyl groups: Unusual head-to-tail coupling of terphenyl moieties
  作者：Corneliu Stanciu、Alexander R. Fox、Anne F. Richards、James C. Fettinger、Philip P. Power

  DOI：10.1016/j.jorganchem.2006.01.047

  日期：2006.5

  The synthesis and characterization of several ipso-functionalized derivatives of the bulky terphenyl group C6H3-2,6(C6H3-2',6'-Pr-2(i))(2)(Ar') are described. These include the primary alcohol Ar'CH2OH (1), the bromo derivative Ar'CH2Br (2), and the terphenyl formate Ar'CH2OC(O)H (3). The alcohol 1 was obtained by treatment of LiAr' with formaldehyde, and 1 was readily converted to the bromo derivative 2 using HBr. The reaction of 1 with formic acid afforded 3 in good yield. Attempts to form the Grignard derivative of 1, i.e., Ar'CH2MgBr, resulted in a head-to-tail reaction of the terphenyl benzyl units to yield an unusual coupled product 4. An approach to the avoidance of this coupling involved the synthesis of the terphenyl derivatives 1-I-C6H2-2,6(C6H3-2',6'-Pr-2(i))(2)-4-Me (5) and 1-I-C6H2-2,6(C6H2-2',4',6'-Pr-3(i))(2)-4-Me (6), bearing methyl groups in the para positions of the central aryl ring, which could be prepared in good yield, and converted to their respective lithium salts 7 and 8 without complication. The compounds were characterized by H-1 and C-13 NMR spectroscopy, IR spectroscopy (1) and X-ray crystallography (2, 4, 5 and 6). (c) 2006 Elsevier B.V. All rights reserved.