4-(3-(4-(tris(4-tert-butyl-phenyl)methyl)phenoxy)propoxy)phenylboronic acid | 954372-88-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(3-(4-(tris(4-tert-butyl-phenyl)methyl)phenoxy)propoxy)phenylboronic acid
• 英文别名: [4-[3-[4-[Tris(4-tert-butylphenyl)methyl]phenoxy]propoxy]phenyl]boronic acid
• CAS: 954372-88-4
• 化学式: C₄₆H₅₅BO₄
• 分子量: 682.751
• InChiKey: QCOYWFHIRYIQOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.49
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-(4-(tris(4-tert-butyl-phenyl)methyl)phenoxy)propoxy)phenylboronic acid 、 3-(3,3,3-tris(4-chlorophenyl)propanoyloxy)propyl acrylate 在 (R)-4-benzyl-2-(2-((S)-4-phenyl-4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole 、 氧气 、 palladium diacetate 、 对苯醌 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis of a C1-symmetric Box macrocycle and studies towards active-template synthesis of mechanically planar chiral rotaxanes

  摘要：

  A C-1-symmetric Box macrocycle has been synthesized for the first time. The Box macrocycle along with other C-1 and C-2-symmetric Box ligands were evaluated and compared as ligands in the Cadiot-Chodkiewicz, oxidative Heck and CuAAC 'click' reactions as part of our studies towards achieving active-metal template synthesis of mechanically planar chiral rotaxanes. This study constitutes the first report of Cadiot-Chodkiewicz and CuAAC 'click' reactions using Box ligands, as well as the first dedicated study of oxidative Heck reactions using Box ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.069
• 作为产物：
  描述：

  4,4',4''-((4-(3-(4-iodophenoxy)propoxy)phenyl)methanetriyl)tris(tert-butylbenzene) 在 正丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 21.5h， 以71%的产率得到4-(3-(4-(tris(4-tert-butyl-phenyl)methyl)phenoxy)propoxy)phenylboronic acid
  参考文献：
  名称：

  [2] 轮烷通过钯活性模板氧化 Heck 交叉偶联

  摘要：

  Pd(II) 催化的交叉偶联已被用于通过活性金属模板策略有效合成 [2] 轮烷。该反应高效、温和且具有底物耐受性，并且仅使用催化量的 Pd(II) 模板。相比之下，尝试使用传统的 Pd(0) 催化交叉偶联仅导致非互锁螺纹和轮烷。

  DOI：

  10.1021/ja075219t

文献信息

• Synthesis of a C1-symmetric Box macrocycle and studies towards active-template synthesis of mechanically planar chiral rotaxanes
  作者：Pauline E. Glen、James A.T. O'Neill、Ai-Lan Lee

  DOI：10.1016/j.tet.2012.10.069

  日期：2013.1

  A C-1-symmetric Box macrocycle has been synthesized for the first time. The Box macrocycle along with other C-1 and C-2-symmetric Box ligands were evaluated and compared as ligands in the Cadiot-Chodkiewicz, oxidative Heck and CuAAC 'click' reactions as part of our studies towards achieving active-metal template synthesis of mechanically planar chiral rotaxanes. This study constitutes the first report of Cadiot-Chodkiewicz and CuAAC 'click' reactions using Box ligands, as well as the first dedicated study of oxidative Heck reactions using Box ligands. (C) 2012 Elsevier Ltd. All rights reserved.
• [2]Rotaxanes through Palladium Active-Template Oxidative Heck Cross-Couplings
  作者：James D. Crowley、Kevin D. Hänni、Ai-Lan Lee、David A. Leigh

  DOI：10.1021/ja075219t

  日期：2007.10.1

  Pd(II)-catalyzed cross-couplings have been utilized in the efficient synthesis of [2]rotaxanes via an active-metal template strategy. The reaction is efficient, mild, and substrate-tolerant and uses only catalytic amounts of the Pd(II) template. In contrast, attempts using traditional Pd(0)-catalyzed cross-couplings led only to non-interlocked thread and no rotaxane.

  Pd(II) 催化的交叉偶联已被用于通过活性金属模板策略有效合成 [2] 轮烷。该反应高效、温和且具有底物耐受性，并且仅使用催化量的 Pd(II) 模板。相比之下，尝试使用传统的 Pd(0) 催化交叉偶联仅导致非互锁螺纹和轮烷。