(i-PrO)Me2SiB(pin) | 929887-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 溴苄基硼酸频哪醇酯
• 英文名称: (i-PrO)Me2SiB(pin)
• 英文别名: 2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；Dimethyl-propan-2-yloxy-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane；dimethyl-propan-2-yloxy-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
• CAS: 929887-20-7
• 化学式: C₁₁H₂₅BO₃Si
• 分子量: 244.214
• InChiKey: ZZJBYTAQGMWUFL-UHFFFAOYSA-N

物化性质

• 沸点：
  213.7±23.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  (i-PrO)Me2SiB(pin) 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-双(二苯基膦)丙烷 、 2-(2-butynyl)-2-(2,4-pentadienyl)malonic acid diethyl ester 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以71%Spectr.的产率得到异丙醇频哪醇硼酸酯
  参考文献：
  名称：

  硅基铑催化[4 + 2 +1]环加成反应制备含硅七元环

  摘要：

  建立了铑催化的[4 + 2 + 1]环加成反应，该反应涉及1,3-二烯，炔烃和亚甲硅烷基，以提供含硅的七元环。在带有双（二苯基膦基）甲烷（DPPM）的铑催化剂的存在下，壬基1,3-三烯-8-炔衍生物在80–110°C下与硼基（异丙氧基）硅烷或硼基（二乙氨基）硅烷有效反应，其作为亚甲硅烷基的合成当量反应，得到1-silacyclohepta-2，5-二烯（2，5-二氢-1 H-西勒平）。七元非共轭二烯的区域发散性和化学和立体选择性官能化是通过Cs 2 CO 3或铱催化剂介导的硼氢化作用实现的。

  DOI：

  10.1021/acs.orglett.0c00690
• 作为产物：
  描述：

  (chlorodimethylsilyl)pinacolborane 、 异丙醇 在 吡啶 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 以90%的产率得到(i-PrO)Me2SiB(pin)
  参考文献：
  名称：

  Synthesis of Silylboronic Esters Functionalized on Silicon

  摘要：

  New silylpinacolboranes bearing chloro, fluoro, alkoxy, and dialkylamino groups on silicon were synthesized in high yields via derivatization of [(diethylamino)diphenylsilyl]pinacolborane, which was prepared by reaction of [(diethylamino)diphenylsilyl]lithium with (isopropoxy)pinacolborane, and (chlorodimethylsilyl)pinacolborane, prepared by reaction of (dimethylphenylsilyl)pinacolborane with hydrogen chloride in the presence of a catalytic amount of aluminum chloride.

  DOI：

  10.1021/om0609867
• 作为试剂：
  描述：

  2-(2-butynyl)-2-(2,4-pentadienyl)malonic acid diethyl ester 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (i-PrO)Me2SiB(pin) 、 1,5-双(二苯基膦)戊烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以46%的产率得到diethyl 7-methyl-1,3,3a,6-tetrahydro-2H-indene-2,2-dicarboxylate
  参考文献：
  名称：

  硅基铑催化[4 + 2 +1]环加成反应制备含硅七元环

  摘要：

  建立了铑催化的[4 + 2 + 1]环加成反应，该反应涉及1,3-二烯，炔烃和亚甲硅烷基，以提供含硅的七元环。在带有双（二苯基膦基）甲烷（DPPM）的铑催化剂的存在下，壬基1,3-三烯-8-炔衍生物在80–110°C下与硼基（异丙氧基）硅烷或硼基（二乙氨基）硅烷有效反应，其作为亚甲硅烷基的合成当量反应，得到1-silacyclohepta-2，5-二烯（2，5-二氢-1 H-西勒平）。七元非共轭二烯的区域发散性和化学和立体选择性官能化是通过Cs 2 CO 3或铱催化剂介导的硼氢化作用实现的。

  DOI：

  10.1021/acs.orglett.0c00690

文献信息

• Catalytic Generation of Rhodium Silylenoid for Alkene–Alkyne–Silylene [2 + 2 + 1] Cycloaddition
  作者：Toshimichi Ohmura、Ikuo Sasaki、Michinori Suginome

  DOI：10.1021/acs.orglett.9b00326

  日期：2019.3.15

  2 + 1] cycloaddition takes place in the rhodium-catalyzed reaction of 1,6-enynes with borylsilanes bearing an alkoxy group on the silicon atoms, which react as synthetic equivalents of silylene. The reaction proceeds efficiently in 1,2-dichloroethane at 80–110 °C in the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM) as a ligand to afford 1-silacyclopent-2-enes in good to

  烯烃-炔烃-亚甲基[2 + 2 +1]的环加成反应是在铑催化的1,6-炔烃与在硅原子上带有烷氧基的硼烷基硅烷的反应中进行的，这些硅烷作为合成的甲硅烷基等效物进行反应。在载有双（二苯基膦基）甲烷（DPPM）作为配体的铑催化剂存在下，反应在80-110°C的1,2-二氯乙烷中有效进行，从而以高收率或高收率得到1-silacyclopent-2-enes。
• Copper-catalyzed regioselective <i>trans</i>-silaboration of internal arylalkynes with stereochemical switch to <i>cis</i>-addition mode
  作者：Toshimichi Ohmura、Yuta Takaoka、Michinori Suginome

  DOI：10.1039/d1cc01579f

  日期：——

  Copper-catalyzed silafunctionalization of alkynes using a silylboronic ester as a silicon source has recently progressed rapidly. Generally, the reaction affords a product with cis-stereoselectivity. We herein describe trans-selective 1,2-addition of silylboronic esters to internal arylalkynes, which was promoted efficiently by the CuOt-Bu/RCy2P/NaOt-Bu catalysts. Moreover, we report a stereochemical

  使用甲硅烷基硼酸酯作为硅源的炔烃的铜催化的硅烷基化最近进展迅速。通常，该反应提供具有顺式-立体选择性的产物。我们在本文中描述了甲硅烷基硼酸酯向内部芳基炔烃的反式选择性1，2-加成，其通过CuO t -Bu / RCy 2 P / NaO t -Bu催化剂有效地促进。此外，我们报道了在包括环己烷在内的烃类溶剂中，Me 2（i -PrO）Si–B（pin）的反应中立体化学转换为顺式加成。
• <i>Anti</i>-Selective Vicinal Silaboration and Diboration of Alkynoates through Phosphine Organocatalysis
  作者：Kazunori Nagao、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/acs.orglett.5b00305

  日期：2015.3.6

  Trialkylphosphine organocatalysts have enabled anti-selective vicinal silaboration and diboration of the C-C triple bond in alkynoates to produce beta-boryl-alpha-silyl acrylates and alpha,beta-diboryl acrylates, respectively. The anti stereoselectivity was complete and robust. A variety of functional groups were tolerated in the alkynoates. The two vicinally installed heteroatom substituents of the beta-boryl-alpha-silyl acrylates and alpha,beta-diboryl acrylates could be differentiated and transformed in a stepwise manner, allowing the synthesis of a diverse array of unsymmetrical tetrasubstituted alkenes.
• Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid
  作者：Ikuo Sasaki、Toshimichi Ohmura、Michinori Suginome

  DOI：10.1021/acs.orglett.0c00690

  日期：2020.4.17

  involving 1,3-diene, alkyne, and silylene to afford silicon-containing seven-membered rings was established. In the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM), nona-1,3-dien-8-yne derivatives reacted efficiently at 80–110 °C with boryl(isopropoxy)silane or boryl(diethyamino)silane, which reacts as the synthetic equivalent of silylene, to afford 1-silacyclohepta-2,5-dienes (2

  建立了铑催化的[4 + 2 + 1]环加成反应，该反应涉及1,3-二烯，炔烃和亚甲硅烷基，以提供含硅的七元环。在带有双（二苯基膦基）甲烷（DPPM）的铑催化剂的存在下，壬基1,3-三烯-8-炔衍生物在80–110°C下与硼基（异丙氧基）硅烷或硼基（二乙氨基）硅烷有效反应，其作为亚甲硅烷基的合成当量反应，得到1-silacyclohepta-2，5-二烯（2，5-二氢-1 H-西勒平）。七元非共轭二烯的区域发散性和化学和立体选择性官能化是通过Cs 2 CO 3或铱催化剂介导的硼氢化作用实现的。
• Synthesis of Silylboronic Esters Functionalized on Silicon
  作者：Toshimichi Ohmura、Kohei Masuda、Hideki Furukawa、Michinori Suginome

  DOI：10.1021/om0609867

  日期：2007.2.1

  New silylpinacolboranes bearing chloro, fluoro, alkoxy, and dialkylamino groups on silicon were synthesized in high yields via derivatization of [(diethylamino)diphenylsilyl]pinacolborane, which was prepared by reaction of [(diethylamino)diphenylsilyl]lithium with (isopropoxy)pinacolborane, and (chlorodimethylsilyl)pinacolborane, prepared by reaction of (dimethylphenylsilyl)pinacolborane with hydrogen chloride in the presence of a catalytic amount of aluminum chloride.