(Z)-2-(3-phenylallyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 147609-47-0

• 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: (Z)-2-(3-phenylallyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: cinnamylboronic acid pinacol ester；(Z)-PhCHCHCH2BO2(CMe2)2；4,4,5,5-tetramethyl-2-[(Z)-3-phenylprop-2-enyl]-1,3,2-dioxaborolane
• CAS: 147609-47-0
• 化学式: C₁₅H₂₁BO₂
• 分子量: 244.142
• InChiKey: KRBDLBBKFWUBQY-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-β-bromostyrene 、 iodozinc(1+),2-methanidyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到(Z)-2-(3-phenylallyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  通过钯催化Knochel（二烷氧基硼基）甲基锌试剂与1-卤-1-烯烃的交叉偶联反应立体选择合成烯丙基硼酸盐

  摘要：

  三苯基膦或三苯基ar基钯配合物催化（二烷氧基硼基）甲基锌试剂IZnCH 2 B（OR）2与1-卤代-1-烯烃的交叉偶联反应，从而提供具有立体选择性的立体定义的烯丙基硼酸的酯。通过羰基的第一次分子内烯丙基硼化反应以提供环状醇。

  DOI：

  10.1016/0022-328x(93)83081-6

文献信息

• Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction
  作者：William B. Reid、Jesse J. Spillane、Sarah B. Krause、Donald A. Watson

  DOI：10.1021/jacs.6b02914

  日期：2016.5.4

  example of a boryl-Heck reaction using an electrophilic boron reagent. This palladium-catalyzed process allows for the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available catecholchloroborane (catBCl). In situ transesterification allows for rapid access to a variety of boronic esters, amides, and other alkenyl boron adducts.

  我们报告了使用亲电子硼试剂进行硼基-赫克反应的第一个例子。这种钯催化的过程允许使用市售的儿茶酚氯硼烷 (catBCl) 将末端烯烃转化为反式烯基硼酸酯。原位酯交换可以快速获得各种硼酸酯、酰胺和其他烯基硼加合物。
• Cross-Metathesis/Isomerization/Allylboration Sequence for a Diastereoselective Synthesis of<i>Anti</i>-Homoallylic Alcohols from Allylbenzene Derivatives and Aldehydes
  作者：Rémy Hemelaere、François Carreaux、Bertrand Carboni

  DOI：10.1002/chem.201403954

  日期：2014.10.27

  We describe a highly diastereoselective approach to anti‐homoallylic alcohols from allylbenzene derivatives and aldehydes. The strategy is based on a cross‐metathesis/isomerization/allylboration sequence catalyzed successively by ruthenium and iridium. This methodology provides another way to access this class of compounds, which leads to the preparation of hitherto‐unknown homoallylic alcohols without

  我们描述一个高立体选择性的方法来防从苯丙烯衍生物和醛类-homoallylic醇。该策略基于钌和铱连续催化的交叉复分解/异构化/烯丙基化序列。这种方法学提供了另一种获取此类化合物的方法，从而无需控制1-烯基硼酸酯中间体的立体化学即可制备迄今未知的均丙醇。还报道了我们对这种顺序反应的对映体选择性的研究。
• Direct Light‐Enabled Access to α‐Boryl Radicals: Application in the Stereodivergent Synthesis of Allyl Boronic Esters**
  作者：Alessandro Marotta、Hao Fang、Callum E. Adams、Kailey Sun Marcus、Constantin G. Daniliuc、John J. Molloy

  DOI：10.1002/anie.202307540

  日期：2023.8.21

  C−C bond formation. We disclose a facile activation of α-halo boronic esters using light and a Lewis base to permit homolytic scission. Addition to styrenes allows the construction of E-allylic boronic esters. The simplicity of activation permits the strategic merger with energy transfer catalysis to enable the stereodivergent synthesis of Z-isomers.

  α-硼基自由基作为多功能中间体重新出现，通过相邻的 C−C 键形成来获取有机硼。我们公开了使用光和路易斯碱轻松活化α-卤代硼酸酯以允许均裂。添加到苯乙烯中可以构建E-烯丙基硼酸酯。活化的简单性允许与能量转移催化的战略合并，从而实现Z异构体的立体发散合成。
• Boronyl Borinic Esters: Preparation as B₂pin₂/^<i>sec</i>BuLi/TFAA Adducts, Structural Insights and Reactivity in Pd‐catalyzed Allylic Borylation
  作者：Maxim A. Novikov、Roman A. Novikov、Yury V. Tomilov

  DOI：10.1002/asia.202300219

  日期：2023.6.15

  Novel class of diboron reagent – boronyl borinic ester – was developed that were generated as B2pin2/secBuLi/TFAA adducts. Detailed NMR with solid-state 2D NMR techniques and ESI-MS investigations were used to get structural insights of these new reagents. The new boronyl borinic esters were proved to be promising for allylic borylations of base-sensitive substrates.

  开发了新型二硼试剂——硼酰基硼酸酯——生成为 B 2 pin 2 / sec BuLi/TFAA 加合物。详细的核磁共振与固态二维核磁共振技术和 ESI-MS 研究被用于获得这些新试剂的结构洞察力。新的硼酰基硼酸酯被证明有望用于碱敏感底物的烯丙基硼化。
• Stereoselective synthesis of allylic boronates via palladium-catalyzed cross-coupling reaction of Knochel's (dialkoxyboryl) methylzinc reagents with 1-halo-1-alkenes
  作者：Takeo Watanabe、Norio Miyaura、Akira Suzuki

  DOI：10.1016/0022-328x(93)83081-6

  日期：1993.2

  The cross-coupling reaction of (dialkoxyboryl)methylzinc reagents IZnCH2B(OR)2 with 1-halo-1-alkenes was catalysed by triphenyl-phosphine- or triphenylarsine-based palladium complexes to provide esters of stereodefined allylboronic acids with stereoselectivity. The reaction was applied to provide a cyclic alcohol via the first intramolecular allylboration of carbonyl.

  三苯基膦或三苯基ar基钯配合物催化（二烷氧基硼基）甲基锌试剂IZnCH 2 B（OR）2与1-卤代-1-烯烃的交叉偶联反应，从而提供具有立体选择性的立体定义的烯丙基硼酸的酯。通过羰基的第一次分子内烯丙基硼化反应以提供环状醇。