(R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-tolylpropan-1-one | 1420161-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-tolylpropan-1-one
• 英文别名: (3R)-1-(4-methylphenyl)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-one
• CAS: 1420161-29-0
• 化学式: C₂₂H₂₇BO₃
• 分子量: 350.266
• InChiKey: VRZNYHJJTZBVLJ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-tolylpropan-1-one 在 sodium perborate 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-3-hydroxy-3-phenyl-1-(p-tolyl)-propan-1-one
  参考文献：
  名称：

  POLYNORBORNENE/CARBON BLACK-CROSS-LINKED THREE-DIMENSIONAL NETWORK-IMMOBILIZED COPPER/GOLD (PNBI/CB-Cu/Au) NANOCATALYST, AND PREPARATION METHOD AND USE THEREOF

  摘要：

  The present disclosure belongs to the technical field of catalyst preparation, and provides a polynorbornene/carbon black-cross-linked three-dimensional network-immobilized bimetallic copper/gold (PNBI/CB-Cu/Au) nanocatalyst, and a preparation method and use thereof. Metallic copper and gold both exist in a form of nanoparticles in the catalyst and are uniformly dispersed, and further enhancing a catalytic performance. Moreover, the carrier is a polynorbornene/carbon black-cross-linked three-dimensional network, and a relative content of free hydroxyl groups in the catalyst is controlled by changing a monomer ratio to adjust a hydrophilic-lipophilic balance value of the catalyst, adapting to a reaction of an organic phase with an aqueous phase. Furthermore, the catalyst is insoluble in conventional solvents, and has a desirable effect in immobilizing nanoscale metallic copper, prolonging a service life of the catalyst.

  公开号：

  US20240261768A1
• 作为产物：
  描述：

  苯甲醛 在 (S)-2-{[(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl}phenol 、 copper diacetate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 (R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-tolylpropan-1-one 、 (S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-tolylpropan-1-one
  参考文献：
  名称：

  化学和生物催化方法的级联反应，以获得手性羟基酮和抗1,3-二醇。

  摘要：

  化学和生物催化级联方法用于羟基酮和相应的1,3-二醇的立体选择性合成。一类新的三齿N，N，O配体与铜（II）配合物一起用于α，β-不饱和化合物的不对称β-硼化。含有配体L5的配合物表现出最好的表现，它使有机硼烷衍生物具有良好的ee值。相应的酮醇化合物随后被酵母生物还原。生物转化设置与深红酵母允许（[R ）酮醇和（小号，小号）-diols要与高达99％得到的 ee值和高达99％的 德赞成抗对映体。

  DOI：

  10.1002/open.201800056

文献信息

• Enantioselective β-Boration of Acyclic Enones by a [2.2]Paracyclophane-Based N-Heterocyclic Carbene Copper(I) Catalyst
  作者：Lei Zhao、Yudao Ma、Fuyan He、Wenzeng Duan、Jianqiang Chen、Chun Song

  DOI：10.1021/jo302694d

  日期：2013.2.15

  N-heterocyclic carbene (NHC) copper(I) complex generated in situ by the reaction of the triazolium salt and Cu2O was an efficient catalyst for the asymmetric β-boration of acyclic enones, producing β-boryl ketones in high yields and enantioselectivities.

  一种新的平面和中心手性双环1,2,4-三唑鎓盐是由[2.2]对环环烷和苯基甘醇合成的。三唑盐和Cu 2 O反应原位生成的N-杂环卡宾（NHC）铜（I）络合物是一种有效的催化剂，用于无环烯酮的不对称β-硼化，可高产率地生产β-硼酮和对映选择性。
• Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones
  作者：Lei Wang、Zhen Chen、Manyuan Ma、Wenzeng Duan、Chun Song、Yudao Ma

  DOI：10.1039/c5ob01609f

  日期：——

  An enantioselective conjugate addition of boron to α,β-unsaturated ketones catalysed by either a N-heterocyclic carbene or a copper–carbene complex generated in situ from a new chiral bicyclic triazolium based on [2.2]paracyclophane is presented. The dual chiral carbene–copper catalyst has significant advantages over its carbene counterpart as an organocatalyst in asymmetric β-boration of acyclic enones

  提出了一种硼的对映选择性共轭加成反应，该加氢反应由N杂环卡宾或由基于[2.2]对环phane的新手性双环三唑鎓盐就地生成的N杂环卡宾或铜-卡宾配合物催化。双手性卡宾-铜催化剂在作为非环烯酮的不对称β-硼酸酯化反应的有机催化剂时，具有比其卡宾对应物显着的优势，从而以良好的收率和对映选择性提供了多种手性β-硼基酮。这是在一个催化反应中使用相同的N-杂环卡宾作为有机催化剂和过渡金属催化的配体的成功例子。
• Synthesis of fluorine-substituted [2.2]paracyclophane-based carbene precursors for copper-catalyzed enantioselective boration of α,β-unsaturated ketones
  作者：Linyong Wang、Meng Ye、Lei Wang、Wenzeng Duan、Chun Song、Yudao Ma

  DOI：10.1016/j.tetasy.2016.12.005

  日期：2017.1

  Fluorine-substituted [2.2]paracyclophane-based carbene precursors have been successfully synthesized and applied to copper-catalyzed asymmetric beta-boration of alpha,beta-unsaturated ketones. Fluorination of the planar chiral carbenes has a beneficial impact on the catalytic performance of the relevant complexes. A variety of chiral beta-boryl ketones were obtained in excellent yields (up to 99%) and with high enantioselectivities (up to 99% ee). (C) 2016 Elsevier Ltd. All rights reserved.
• Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and <i>anti</i> 1,3-Diols
  作者：Raffaella Gandolfi、Giorgio Facchetti、Michael S. Christodoulou、Marco Fusè、Fiorella Meneghetti、Isabella Rimoldi

  DOI：10.1002/open.201800056

  日期：2018.5

  biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3‐diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β‐borylation of α,β‐unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol

  化学和生物催化级联方法用于羟基酮和相应的1,3-二醇的立体选择性合成。一类新的三齿N，N，O配体与铜（II）配合物一起用于α，β-不饱和化合物的不对称β-硼化。含有配体L5的配合物表现出最好的表现，它使有机硼烷衍生物具有良好的ee值。相应的酮醇化合物随后被酵母生物还原。生物转化设置与深红酵母允许（[R ）酮醇和（小号，小号）-diols要与高达99％得到的 ee值和高达99％的 德赞成抗对映体。
• POLYNORBORNENE/CARBON BLACK-CROSS-LINKED THREE-DIMENSIONAL NETWORK-IMMOBILIZED COPPER/GOLD (PNBI/CB-Cu/Au) NANOCATALYST, AND PREPARATION METHOD AND USE THEREOF
  申请人：HUBEI ENGINEERING UNIVERSITY

  公开号：US20240261768A1

  公开（公告）日：2024-08-08

  The present disclosure belongs to the technical field of catalyst preparation, and provides a polynorbornene/carbon black-cross-linked three-dimensional network-immobilized bimetallic copper/gold (PNBI/CB-Cu/Au) nanocatalyst, and a preparation method and use thereof. Metallic copper and gold both exist in a form of nanoparticles in the catalyst and are uniformly dispersed, and further enhancing a catalytic performance. Moreover, the carrier is a polynorbornene/carbon black-cross-linked three-dimensional network, and a relative content of free hydroxyl groups in the catalyst is controlled by changing a monomer ratio to adjust a hydrophilic-lipophilic balance value of the catalyst, adapting to a reaction of an organic phase with an aqueous phase. Furthermore, the catalyst is insoluble in conventional solvents, and has a desirable effect in immobilizing nanoscale metallic copper, prolonging a service life of the catalyst.