2,2'-(3-(benzyloxy)propane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) | 1227056-28-1

• 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: 2,2'-(3-(benzyloxy)propane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 英文别名: 3-benzyloxy-1,1-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propane；4,4,5,5-Tetramethyl-2-[3-phenylmethoxy-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-1,3,2-dioxaborolane
• CAS: 1227056-28-1
• 化学式: C₂₂H₃₆B₂O₅
• 分子量: 402.147
• InChiKey: XHQDOROGJVNZSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2'-(3-(benzyloxy)propane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 在 四(三苯基膦)钯 、 (3aR,8aR)-N,N,2,2-tetramethyl-4,4,8,8-tetra-p-tolyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine 、 palladium diacetate 、 potassium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 28.0h， 生成 (R)-2-(3-(benzyloxy)-1-phenylpropyl)-1-methoxy-4-methylbenzene
  参考文献：
  名称：

  A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

  摘要：

  Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral B-10-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon.

  DOI：

  10.1021/ja500029w
• 作为产物：
  描述：

  苄基-2-丙炔胺 、 频那醇硼烷 在 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.17h， 以80%的产率得到2,2'-(3-(benzyloxy)propane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
  参考文献：
  名称：

  铜通过末端炔烃的区域选择性二氢硼化反应催化合成1,1-二硼烷基烷烃

  摘要：

  研究了用频哪醇硼烷在铜催化下的末端炔烃连续加氢硼化反应，从而直接从炔烃制备1,1-二硼烷基烷烃。受保护的炔丙基胺，炔丙醇衍生物和简单炔烃可在铜/黄磷催化剂下以高收率选择性地生成所需的1,1-二硼烷基烷烃。

  DOI：

  10.1002/asia.201402458

文献信息

• Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
  作者：Kai Hong、Xun Liu、James P. Morken

  DOI：10.1021/ja505455z

  日期：2014.7.30

  The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

  1,1-双(频哪醇硼酸酯)酯与烷基卤化物的反应可以通过金属醇盐进行，并为构建有机硼酸酯化合物提供了策略。发现该反应通过醇盐诱导的脱硼和硼稳定的碳负离子的生成而发生。
• Stereoselective Synthesis of Tetrasubstituted Alkenylboronates via 1,1-Organodiboronates
  作者：Kohei Endo、Munenao Hirokami、Takanori Shibata

  DOI：10.1021/jo1003407

  日期：2010.5.21

  The stereoselective synthesis of tetrasubstituted alkenylboronates was established via the lithiation/nucleophilic addition reaction of 1,1-orizanodiboronates to carbonyl compounds. The present approach enables the facile and practical synthesis of tetrasubstituted olefins, which are useful synthetic intermediates for further functionalizations.
• Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp³-Carbon in 1,1-Diborylalkanes at Room Temperature
  作者：Kohei Endo、Takahiro Ohkubo、Munenao Hirokami、Takanori Shibata

  DOI：10.1021/ja105176v

  日期：2010.8.18

  The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.