2-(Tetrahydrofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 331958-88-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 2-(Tetrahydrofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-Tetramethyl-2-tetrahydrofuran-2-yl-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-(oxolan-2-yl)-1,3,2-dioxaborolane
• CAS: 331958-88-4
• 化学式: C₁₀H₁₉BO₃
• 分子量: 198.07
• InChiKey: NRIHVWDOPTVSAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(5-bromo-3-(trifluoromethyl)-1H-pyrazol-1-yl)butan-2-yl (2,4-difluorophenyl)carbamate 、 2-(Tetrahydrofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 [(2R)-1-[5-(oxolan-2-yl)-3-(trifluoromethyl)pyrazol-1-yl]butan-2-yl] N-(2,4-difluorophenyl)carbamate
  参考文献：
  名称：

  Synthesis and activity of substituted carbamates as potentiators of the α4β2 nicotinic acetylcholine receptor

  摘要：

  The synthesis and structure-activity relationship of a series of carbamate potentiators of alpha 4 beta 2 nAChR is reported herein. These compounds were highly selective for alpha 4 beta 2 over other nAChR subtypes. In addition, compounds increased the response of alpha 4 beta 2 nAChRs to acetylcholine, as measured with patch-clamp electrophysiology. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.092
• 作为产物：
  描述：

  呋喃-2-硼酸频哪醇酯 在 Rh-CAAC 、 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、5.0 MPa 条件下， 反应 24.0h， 以98%的产率得到2-(Tetrahydrofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  硼化芳烃的加氢

  摘要：

  据报道，环状（烷基）（氨基）卡宾铑（Rh–CAAC）催化了丰富的芳基硼酸及其衍生物的顺式选择性氢化。该反应可耐受各种硼保护基，并可以直接进入具有各种官能团的各种饱和，硼化的碳环和杂环。该转变在战略上很重要，因为通用的饱和硼酸酯产品很难用其他方法制备。硼基的后官能化证明了饱和环状结构单元的效用。

  DOI：

  10.1002/anie.201810714

文献信息

• METHODS FOR FORMING SATURATED (HETERO)CYCLIC BORYLATED HYDROCARBONS AND RELATED COMPOUNDS
  申请人：BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY

  公开号：US20180051042A1

  公开（公告）日：2018-02-22

  The disclosure relates to methods for forming at least partially saturated cyclic and heterocyclic borylated hydrocarbons, as well as related compounds, which can be precursor compounds in the synthesis of any of a variety of pharmaceutical or medicinal compounds with a desired structure and/or stereochemistry for drug synthesis or drug candidate evaluation. The methods generally include reduction of an unsaturated cyclic or heterocyclic borylated hydrocarbon having a boron-containing substituent at an sp 2 -carbon, where such reduction converts the sp 2 -carbon to an sp 3 -carbon at the point of attachment of the boron-containing substituent. The methods can exhibit a selectivity for syn-addition during reduction, which can provide stereospecific products, such as when the unsaturated cyclic or heterocyclic reactant is multiply substituted with boron groups and/or other functional groups.

  本发明涉及用于形成至少部分饱和的环状和杂环硼化烃的方法，以及相关的化合物，这些化合物可以是合成多种具有所需结构和/或立体化学的药物或药用化合物的前体化合物。这些方法通常包括将具有sp2碳上含硼取代基的不饱和环状或杂环硼化烃还原，这样的还原将sp2碳转化为与含硼取代基连接点上的sp3碳。这些方法在还原过程中可表现出对顺式加成的选择性，从而可以提供立体特异性产物，例如当不饱和环状或杂环反应物上多元取代硼基团和/或其他功能基团时。
• Combining high pressure and catalysis: pinacol- or catecholborane hydroboration of functionalized olefins†
  作者：Sylvie Colin、Lucile Vaysse-Ludot、Jean-Pierre Lecouvé、Jacques Maddaluno

  DOI：10.1039/b004275g

  日期：——

  The hydroboration of three families of functionalized olefins (1-bromo- and 1,3-dibromopropenes, allylamines, 2,3-dihydrofuran) by pinacolborane and catecholborane has been studied under various experimental conditions. For 1-bromo- and 1,3-dibromopropenes, pinacolborane (PBH) is a poor reagent that requires the use of high pressure in ethereal solvents and provides only by-products, resulting from

  这 水硼化 的三个功能化家族 烯烃 （1-溴和1,3-二溴丙烯，烯丙胺， 2,3-二氢呋喃）by pinacolborane and 儿茶酚硼烷已经在各种实验条件下进行了研究。对于1-溴和1,3-二溴丙烯，频哪醇硼烷（PBH）是较差的试剂，需要在醚中使用高压溶剂并且仅提供由不希望的β-溴硼酸酯区域异构体产生的副产物。相比之下，儿茶酚硼烷（CBH）在大气压下主要提供预期的α-溴硼酸盐。和二苄基烯丙胺不论压力如何，PBH都会产生两种可能的区域异构体（β-和γ-氨基硼酸酯）的混合物，而CBH在大气热条件下能以良好的产率选择性地提供预期的γ-异构体。为了2,3-二氢呋喃，当结合0.5％威尔金森氏效应时，只有PBH在THF中可以有效地获得相应的α-和β-区域异构体的混合物 催化剂 和高压。
• Phosphorus Heterocycles: From Laboratory Curiosities to Ligands in Highly Efficient Catalysts
  作者：Lothar Weber

  DOI：10.1002/1521-3773(20020215)41:4<563::aid-anie563>3.0.co;2-q

  日期：2002.2.15

  however, it was reported that transition metal complexes with phosphabenzene and phosphaferrocene ligands exhibit remarkable potential as catalysts. Catalysts based on rhodium (i) and various phosphabenzenes appear to be superior to classical systems in the hydroformylation of terminal and internal alkenes. In addition planar-chiral phosphaferrocene species display an excellent performance as directing

  磷苯和磷二茂铁是最早具有 PC 多键的化合物之一。近 30 年来，这些分子的化学性质基本上是留给基础研究人员的领域。然而，最近据报道，过渡金属配合物与磷苯和磷铁茂配体表现出显着的催化剂潜力。基于铑 (i) 和各种磷苯的催化剂在末端和内部烯烃的加氢甲酰化方面似乎优于经典系统。此外，平面手性磷二茂铁物种在一系列对映选择性不对称合成中作为定向配体表现出优异的性能。
• Access to C(sp3) borylated and silylated cyclic molecules: hydrogenation of corresponding arenes and heteroarenes
  作者：Arzoo Chhabra、Sabrina Reich、Timothy M. Shannon、Robert E. Maleczka、Milton R. Smith

  DOI：10.1039/d4ra00491d

  日期：——

  Readily available and bench stable catalyst. Tolerates a variety of functional groups including orthogonal functionality. Circumvents the limitations of sp3 C–H borylation.