1,1-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene]cyclohexane | 339166-85-7

• 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: 1,1-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene]cyclohexane
• 英文别名: 1,1-{bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene}cyclohexane；[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene]cyclohexane；1,1-(diborylmethylene) cyclohexane；2-[Cyclohexylidene-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 339166-85-7
• 化学式: C₁₉H₃₄B₂O₄
• 分子量: 348.099
• InChiKey: DMUJVZLYLRUSRM-UHFFFAOYSA-N

物化性质

• 沸点：
  359.8±52.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene]cyclohexane 在 四(三苯基膦)钯 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 4-cyclohexylidene-4-phenyl-1-butene
  参考文献：
  名称：

  Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons

  摘要：

  A novel and efficient method for gem-dimetalation of carbenoids has been demonstrated. Treatment of alkylidene-type lithium carbenoids with such an interelement compound as silylborane or diboron to generate the corresponding borate complex, followed by warming to room temperature, induced migration of the silyl or boryl group from a negatively charged boron atom to the carbenoid carbon to afford 1-boryl-1-silyl-1-alkenes or 1,1-diboryl-1-alkenes in good yields. Carbon-carbon bond forming transformations of the gem-dimetalated compounds mediated by boron or silicon is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00648-8
• 作为产物：
  描述：

  环己酮 在 正丁基锂 、 三苯基膦 作用下， 生成 1,1-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene]cyclohexane
  参考文献：
  名称：

  通过供体稳定的乙烯基碳阳离子中间体对乙烯基硼酸盐进行电化学氟化**

  摘要：

  乙烯基碳阳离子是通过使用电位对烯基硼酸盐进行单电子氧化而产生的。这种电化学过程能够在不使用 Lewis 或 Brønsted 酸的情况下形成这些反应性物质。中间乙烯基碳阳离子被亲核氟化物源捕获以产生氟乙烯;还证明了新的 C-C、C-Cl 和 C-Br 键的产生。

  DOI：

  10.1002/anie.202113972

文献信息

• Novel Synthesis of 2,3-Bisboryl-1,3-dienes from 1-Bromo-1-lithioethene and 1,1-Bisborylalkenes
  作者：Masaki Shimizu、Takuya Kurahashi、Tamejiro Hiyama

  DOI：10.1055/s-2001-14647

  日期：——

  Treatment of 1,1-[bis(pinacolato)boryl]alkenes with excess of 1-bromo-1-lithioethene was found to give 2,3-bis[(pinacolato)boryl]-1,3-dienes in moderate to good yields. Synthetic applications of 2,3-[bis(pinacolato)boryl]-1,3-butadiene were also demonstrated.

  研究发现，用过量的 1-溴-1-二硫代乙烯处理 1,1-[双(频哪醇)硼烷基]烯烃可得到 2,3-双[(频哪醇)硼烷基]-1,3-二烯，收率中等至良好。此外，还展示了 2,3-[双(频哪醇)硼烷基]-1,3-丁二烯的合成应用。
• Palladium/Charcoal-Catalysed Olefin Reduction for the Simple and Efficient Synthesis of Substituted gem-Diborylalkanes
  作者：Santanu Panda、Kanak Kanti Das、Debraj Ghorai、Somenath Mahato

  DOI：10.1055/a-2147-1336

  日期：2023.11

  bifunctional reagents that can be applied for the synthesis of simple to complex skeletons. Herein, we report a Pd-catalysed hydrogenation method for the synthesis of gem-diborylalkanes from the corresponding gem-diborylalkenes, which are themselves prepared from the corresponding aldehydes and ketones using known procedures. In addition, transformations of two representative gem-diborylalkane products

  宝石二硼基烷烃最近已成为多种 C-C 键形成反应的有价值的合成子。它们代表了一类重要的双功能试剂，可用于合成简单到复杂的骨架。在此，我们报道了一种由相应的偕二硼基烯烃合成偕二硼基烷烃的Pd催化氢化方法，所述偕二硼基烯烃本身是使用已知的程序由相应的醛和酮制备的。此外，还讨论了两种代表性偕二硼基烷烃产物的转化，从而产生一系列官能化衍生物。
• Geminal Difunctionalization of Alkenylidene-Type Carbenoids by Using Interelement Compounds
  作者：Takeshi Hata、Hirotaka Kitagawa、Hirokazu Masai、Takuya Kurahashi、Masaki Shimizu、Tamejiro Hiyama

  DOI：10.1002/1521-3773(20010216)40:4<790::aid-anie7900>3.0.co;2-t

  日期：2001.2.16
• Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons
  作者：Takuya Kurahashi、Takeshi Hata、Hirokazu Masai、Hirotaka Kitagawa、Masaki Shimizu、Tamejiro Hiyama

  DOI：10.1016/s0040-4020(02)00648-8

  日期：2002.8

  A novel and efficient method for gem-dimetalation of carbenoids has been demonstrated. Treatment of alkylidene-type lithium carbenoids with such an interelement compound as silylborane or diboron to generate the corresponding borate complex, followed by warming to room temperature, induced migration of the silyl or boryl group from a negatively charged boron atom to the carbenoid carbon to afford 1-boryl-1-silyl-1-alkenes or 1,1-diboryl-1-alkenes in good yields. Carbon-carbon bond forming transformations of the gem-dimetalated compounds mediated by boron or silicon is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Electrochemical Fluorination of Vinyl Boronates through Donor‐Stabilized Vinyl Carbocation Intermediates**
  作者：Benjamin Wigman、Woojin Lee、Wenjing Wei、Kendall N. Houk、Hosea M. Nelson

  DOI：10.1002/anie.202113972

  日期：2022.3.14

  Vinyl carbocations were generated via single-electron oxidation of alkenyl boronates using electrical potentials. This electrochemical process enabled the formation of these reactive species without the use of Lewis or Brønsted acids. The intermediate vinyl carbocations were trapped with nucleophilic fluoride sources to yield vinyl fluorides; the production of new C−C, C−Cl, and C−Br bonds was also

  乙烯基碳阳离子是通过使用电位对烯基硼酸盐进行单电子氧化而产生的。这种电化学过程能够在不使用 Lewis 或 Brønsted 酸的情况下形成这些反应性物质。中间乙烯基碳阳离子被亲核氟化物源捕获以产生氟乙烯;还证明了新的 C-C、C-Cl 和 C-Br 键的产生。