[4-[4,6-Bis[4-(hydroxymethyl)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl]methanol | 1404231-77-1

• 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: [4-[4,6-Bis[4-(hydroxymethyl)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl]methanol
• 英文别名: [4-[4,6-bis[4-(hydroxymethyl)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl]methanol
• CAS: 1404231-77-1
• 化学式: C₂₁H₂₁B₃O₆
• 分子量: 401.827
• InChiKey: OSEUCFQPSBXEGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-[4,6-Bis[4-(hydroxymethyl)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl]methanol 、 N-(N-Boc-4-piperidylidene)isopropanesulfinamide 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,2-diphenylphosphinobenzene 、 sodium ethanolate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 以82%的产率得到N-4-(N-Boc-4-(4-(hydroxymethyl)phenyl)piperidinyl)isopropanesulfinylamine
  参考文献：
  名称：

  Rh-Catalyzed Addition of Arylboroxines to Cyclic N-(Isopropanesulfinyl)ketimines

  摘要：

  Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.

  DOI：

  10.1021/jo301634y
• 作为产物：
  描述：

  4-羟甲基苯硼酸 生成 [4-[4,6-Bis[4-(hydroxymethyl)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl]methanol
  参考文献：
  名称：

  Oxidative Heck desymmetrisation of 2,2-disubstituted cyclopentene-1,3-diones

  摘要：

  氧化Heck偶联反应已成功用于2,2-二取代环戊烯-1,3-二酮。直接偶联到2,2-二取代环戊烯-1,3-二酮核心提供了一种新颖、迅速和有用的方法，用于非对称化全碳季铵中心。

  DOI：

  10.1039/c5cc00407a

文献信息

• Oxidative Heck desymmetrisation of 2,2-disubstituted cyclopentene-1,3-diones
  作者：S. E. Walker、C. J. C. Lamb、N. A. Beattie、P. Nikodemiak、A.-L. Lee

  DOI：10.1039/c5cc00407a

  日期：——

  Oxidative Heck couplings have been successfully developed for 2,2-disubstituted cyclopentene-1,3-diones. The direct coupling onto the 2,2-disubstituted cyclopentene-1,3-dione core provides a novel, expedient and useful way of desymmetrising all-carbon quaternary centres.

  氧化Heck偶联反应已成功用于2,2-二取代环戊烯-1,3-二酮。直接偶联到2,2-二取代环戊烯-1,3-二酮核心提供了一种新颖、迅速和有用的方法，用于非对称化全碳季铵中心。
• Rh-Catalyzed Addition of Arylboroxines to Cyclic <i>N</i>-(Isopropanesulfinyl)ketimines
  作者：Hyung Hoon Jung、Andrew W. Buesking、Jonathan A. Ellman

  DOI：10.1021/jo301634y

  日期：2012.11.2

  Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.