1-Cbz-6-(4,4,5,5-四甲基-[1,3,2]二噁硼烷-2-基)-1,2,3,4-四氢吡啶 | 731852-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-Cbz-6-(4,4,5,5-四甲基-[1,3,2]二噁硼烷-2-基)-1,2,3,4-四氢吡啶
• 英文名称: 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
• 英文别名: Benzyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate；benzyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 731852-88-3
• 化学式: C₁₉H₂₆BNO₄
• 分子量: 343.231
• InChiKey: PESXPLPMEBCWQN-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  425.8±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-Cbz-6-(4,4,5,5-四甲基-[1,3,2]二噁硼烷-2-基)-1,2,3,4-四氢吡啶 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 溴苯 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以16%的产率得到N-(苄氧基羰基)-1,2,3,4-四氢吡啶
  参考文献：
  名称：

  A lactam-derived vinyl boronate as a stable and crystalline reagent for the synthesis of 2-substituted piperidines by Pd-catalyzed coupling reactions

  摘要：

  A delta-valerolactam-derived vinyl triflate has been converted into the corresponding vinyl boronate by Pd-catalyzed coupling with bis(pinacolato)diboron, which results in all umpolung. This boronate efficiently couples under Pd catalysis with aryl and heteroaryl bromides to give the corresponding 2-substituted piperidines ill excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.015
• 作为产物：
  描述：

  2-氧代哌啶-1-羧酸苄酯 在 bis-triphenylphosphine-palladium(II) chloride 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 为溶剂， 反应 10.5h， 生成 1-Cbz-6-(4,4,5,5-四甲基-[1,3,2]二噁硼烷-2-基)-1,2,3,4-四氢吡啶
  参考文献：
  名称：

  四氢吡啶-2-硼酸频哪醇酯的制备及Suzuki-Miyaura偶联反应

  摘要：

  进行了将内酰胺衍生的乙烯基三氟甲磺酸酯和磷酸盐转化为相应的硼酸乙烯基酯的研究。δ-戊内酰胺衍生的乙烯基三氟甲磺酸酯可通过Pd与双（频哪醇）二硼烷和频哪醇硼烷，吡咯烷酮和ε-己内酰胺偶合的Pd催化成功地转化为1,4,5,6-四氢吡啶-2-硼酸频哪醇酯衍生物衍生物不反应或容易还原。衍生自δ-戊内酰胺的硼酸乙烯基酯是热稳定的化合物，在Pd催化下可与结构多样的芳基和杂芳基溴化物和三氟甲磺酸酯，乙烯基碘化物和溴化物以及芳族酰氯有效偶联，从而形成相应的2-取代哌啶达到优异的产量。

  DOI：

  10.1021/jo050995+

文献信息

• Synthesis of Acyltrifluoroborates
  作者：Aaron M. Dumas、Jeffrey W. Bode

  DOI：10.1021/ol300668m

  日期：2012.4.20

  Acylboranes are among the most elusive boron-containing organic functional groups, a fact that has impeded development of new reactions employing them as substrates. A new synthesis of acyltrifluoroborates from benzotriazole (Bt)-based N,O-acetals has been developed. Two other routes provide acyltrifluoroborates containing alcohols, aldehydes, and carbamates. The ketone-like reactivity of the acyltrifluoroborate functional group is demonstrated, and the first X-ray structure of an acyltrifluoroborate is reported.
• Preparation and Suzuki−Miyaura Coupling Reactions of Tetrahydropyridine-2-boronic Acid Pinacol Esters
  作者：Ernesto G. Occhiato、Fabrizio Lo Galbo、Antonio Guarna

  DOI：10.1021/jo050995+

  日期：2005.9.1

  6-tetrahydropyridine-2-boronic acid pinacol ester derivatives by Pd-catalyzed coupling reaction with both bis(pinacolato)diboron and pinacolborane, pyrrolidinone and ε-caprolactam derivatives either did not react or were readily reduced. The δ-valerolactam-derived vinyl boronates are thermally stable compounds that efficiently coupled, under Pd catalysis, with structurally diverse aryl and heteroaryl bromides

  进行了将内酰胺衍生的乙烯基三氟甲磺酸酯和磷酸盐转化为相应的硼酸乙烯基酯的研究。δ-戊内酰胺衍生的乙烯基三氟甲磺酸酯可通过Pd与双（频哪醇）二硼烷和频哪醇硼烷，吡咯烷酮和ε-己内酰胺偶合的Pd催化成功地转化为1,4,5,6-四氢吡啶-2-硼酸频哪醇酯衍生物衍生物不反应或容易还原。衍生自δ-戊内酰胺的硼酸乙烯基酯是热稳定的化合物，在Pd催化下可与结构多样的芳基和杂芳基溴化物和三氟甲磺酸酯，乙烯基碘化物和溴化物以及芳族酰氯有效偶联，从而形成相应的2-取代哌啶达到优异的产量。
• A lactam-derived vinyl boronate as a stable and crystalline reagent for the synthesis of 2-substituted piperidines by Pd-catalyzed coupling reactions
  作者：Alessandro Ferrali、Antonio Guarna、Fabrizio Lo Galbo、Ernesto G. Occhiato

  DOI：10.1016/j.tetlet.2004.05.015

  日期：2004.6

  A delta-valerolactam-derived vinyl triflate has been converted into the corresponding vinyl boronate by Pd-catalyzed coupling with bis(pinacolato)diboron, which results in all umpolung. This boronate efficiently couples under Pd catalysis with aryl and heteroaryl bromides to give the corresponding 2-substituted piperidines ill excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.