diisopropyl 5-chloropent-1-ynylboronate | 121198-68-3

• 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: diisopropyl 5-chloropent-1-ynylboronate
• 英文别名: 5-Chloropent-1-ynyl-di(propan-2-yloxy)borane
• CAS: 121198-68-3
• 化学式: C₁₁H₂₀BClO₂
• 分子量: 230.543
• InChiKey: SLCWJUFCRITJPV-UHFFFAOYSA-N

物化性质

• 沸点：
  60 °C(Press: 0.2 Torr)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diisopropyl 5-chloropent-1-ynylboronate 在 chloro(pentamethylcyclopentadienyl)ruthenium(II) tetramer 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 (Z)-2-(1-bromo-5-chloropent-1-en-1-yl)-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
  参考文献：
  名称：

  硼封端炔烃的区域选择性反式氢化锡化

  摘要：

  外围：负载钌催化剂外围的氢键阵列可能是在稳定的炔基-B(aam) 衍生物（aam=蒽酰胺）的氢化锡化过程中观察到优异区域选择性的原因。该反应遵循立体化学非正统的反式加成模式，并提供用于合成的高度通用的宝石二金属化烯烃结构单元。

  DOI：

  10.1002/chem.202101901
• 作为产物：
  描述：

  硼酸三异丙酯 、 5-氯戊炔 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 乙醚 为溶剂， 反应 3.5h， 生成 diisopropyl 5-chloropent-1-ynylboronate
  参考文献：
  名称：

  硼封端炔烃的区域选择性反式氢化锡化

  摘要：

  外围：负载钌催化剂外围的氢键阵列可能是在稳定的炔基-B(aam) 衍生物（aam=蒽酰胺）的氢化锡化过程中观察到优异区域选择性的原因。该反应遵循立体化学非正统的反式加成模式，并提供用于合成的高度通用的宝石二金属化烯烃结构单元。

  DOI：

  10.1002/chem.202101901

文献信息

• Synthesis of multisubstituted 1,3-butadienes using the ruthenium-catalysed double addition of trimethylsilyldiazomethane to alkynylboronates
  作者：Ryotaro Morita、Eiji Shirakawa、Teruhisa Tsuchimoto、Yusuke Kawakami

  DOI：10.1039/b501990g

  日期：——

  alkynylboronates instead of alkynes. Di- and tetrasubstituted 1,3-butadienes were prepared from a 2-boryl-1,4-disilyl-1,3-butadiene, using the Suzuki-Miyaura coupling reaction, iodolysis of the alkenylsilane moieties with N-iodosuccinimide and hydrolysis of the carbon-silicon bonds with trifluoroacetic acid. The same compound was converted also to a bicyclic compound, a trisubstituted 1,3-butadiene and

  Dixneuf和他的同事开发的钌催化的三甲基甲硅烷基重氮甲烷向炔烃的双加成反应被用于合成2-烷基或2-芳基-3-（4,4,5,5-四甲基-1,3,2 -二氧杂硼烷-2-基）-1,4-双（三甲基甲硅烷基）-1，3-丁二烯通过使用炔基硼酸酯而不是炔烃。使用Suzuki-Miyaura偶合反应，烯基硅烷部分与N-碘代琥珀酰亚胺的碘化反应以及二氢呋喃的水解反应，由2-硼基-1,4-二甲硅烷基-1,3-丁二烯制备二和四取代的1,3-丁二烯碳-硅键与三氟乙酸键合。通过Diels-Alder反应，烯基硼酸酯部分的氧化和Mukaiyama aldol反应，将相同的化合物也转化为双环化合物，三取代的1，3-丁二烯和二烯酮。
• Ru(II)-Catalyzed Chemo- and Regioselective Cyclotrimerization of Three Unsymmetrical Alkynes through Boron Temporary Tether. One-Pot Four-Component Coupling via Cyclotrimerization/Suzuki−Miyaura Coupling
  作者：Yoshihiko Yamamoto、Jun-ichi Ishii、Hisao Nishiyama、Kenji Itoh

  DOI：10.1021/ja049673y

  日期：2004.3.1

  The Ru(II)-catalyzed [2+2+2] cyclotrimerization of alkynylboronates, propargyl alcohol, and terminal alkynes proceeded chemo- and regioselectively to give rise to arylboronates, which were subjected to Suzuki-Miyaura cross-coupling with aryliodides to afford highly substituted biaryls in 53-76% yields.

  Ru(II) 催化的炔基硼​​酸酯、炔丙醇和末端炔烃的 [2+2+2] 环三聚反应通过化学和区域选择性进行以产生芳基硼酸酯，然后将芳基硼酸酯与芳基碘化物进行 Suzuki-Miyaura 交叉偶联以提供高度取代的联芳基的产率为 53-76%。
• General synthesis of 2-alkyn-1-ylboronates in excellent isomeric purity
  作者：Raman Soundararajan、Guisheng Li、Herbert C. Brown

  DOI：10.1016/0040-4039(94)88400-5

  日期：1994.11

  2-Alkyn-1-ylboronates have been synthesized successfully, in excellent isomeric purity, via the in situ homologation of alkyn-1-ylboronates with LiCH2I. The relative reactivities exhibited by various LiCH2X reagents (X=Cl; Br; I) are described.

  通过炔基-1-基硼酸酯与LiCH 2 I的原位同源性，已成功以优异的异构体纯度成功合成了2-炔基-1-基硼酸酯。各种LiCH 2 X试剂（X = Cl; Br;一）描述。
• Cp*RuCl-Catalyzed Formal Intermolecular Cyclotrimerization of Three Unsymmetrical Alkynes through a Boron Temporary Tether:  Regioselective Four-Component Coupling Synthesis of Phthalides
  作者：Yoshihiko Yamamoto、Jun-ichi Ishii、Hisao Nishiyama、Kenji Itoh

  DOI：10.1021/ja051377d

  日期：2005.7.1

  Highly substituted phthalides were efficiently synthesized by sequential Cp*RuCl-catalyzed cyclotrimerization of alkynylboronates, propargyl alcohols, and terminal alkynes and palladium(II)-catalyzed carbonylation of the resultant arylboronates. The intermediate arylboronate was isolated and unambiguously characterized by X-ray crystallography. The perfect regioselectivity of the ruthenium-catalyzed formal intermolecular cyclotrimerization was discussed on the basis of the density functional calculations of a boraruthenacycle intermediate.
• One-pot sequential four-component coupling via Cp*RuCl-catalyzed cyclotrimerization and Suzuki–Miyaura coupling
  作者：Yoshihiko Yamamoto、Jun-ichi Ishii、Hisao Nishiyama、Kenji Itoh

  DOI：10.1016/j.tet.2005.08.069

  日期：2005.11

  The catalytic intermolecular cyclotrimerization of alkynylboronates, propargyl alcohols, and terminal alkynes was accomplished by means of the ruthenium catalysis and the temporary tethering approach with the C-B-0 linkage to give rise to highly substituted arylboronates with excellent selectivity. The resultant arylboronates were further converted to highly substituted biaryls via the Suzuki-Miyaura coupling with various aryl iodides using Pd-2(dba)(3)/PCy3 as a catalyst precursor in aqueous toluene. As a consequence, the four-component coupling approach to highly substituted biaryls was successfully established by combining these two operations into a sequential one-pot process. (c) 2005 Elsevier Ltd. All rights reserved.