(E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-ol | 850250-79-2

• 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: (E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-ol
• 英文别名: (3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-ol
• CAS: 850250-79-2
• 化学式: C₁₀H₁₉BO₃
• 分子量: 198.07
• InChiKey: FNGNFKQDRKKGQG-FNORWQNLSA-N

物化性质

• 沸点：
  239.6±42.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-ol 、 tert-butyl 4-(((2-chloro-5-iodopyridin-4-yl)amino)methyl)piperidine-1-carboxylate 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Multiparameter Lead Optimization to Give an Oral Checkpoint Kinase 1 (CHK1) Inhibitor Clinical Candidate: (R)-5-((4-((Morpholin-2-ylmethyl)amino)-5-(trifluoromethyl)pyridin-2-yl)amino)pyrazine-2-carbonitrile (CCT245737)

  摘要：

  Multiparameter optimization of a series of 5((4-aminopyridin-2-yl)amino)pyrazine-carbonitriles resulted in the identification of a potent and selective oral CHK1 preclinical development candidate with in vivo efficacy as a potentiator of deoxyribonucleic acid (DNA) damaging chemotherapy and as a single agent. Cellular mechanism of action assays were used to give an integrated assessment of compound selectivity during optimization resulting in a highly CHK1 selective adenosine triphosphate (ATP) competitive inhibitor. A single substituent vector directed away from the CHK1 kinase active site was unexpectedly found to drive the selective cellular efficacy of the compounds. Both CHK1 potency and off-target human ether-a-go-go-related gene (hERG) ion channel inhibition were dependent on lipophilicity and basicity in this series. Optimization of CHK1 cellular potency and in vivo pharmacokinetic pharmacodynamic (PK-PD) properties gave a compound with low predicted doses and exposures in humans which mitigated the residual weak in vitro hERG inhibition.

  DOI：

  10.1021/acs.jmedchem.5b01938
• 作为产物：
  描述：

  三甲氧基酯 、 2,2'-亚甲基双(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷) 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 bis(η3-allyl-μ-chloropalladium(II)) 、 3-氯丙烯 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 以20%的产率得到(E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-ol
  参考文献：
  名称：

  Pd催化脱氢硼化反应由二[B（pin）]-甲烷与环氧化合物合成硼酸烯基酯

  摘要：

  提出了一种实用且广泛适用的合成（E）-烯基硼的催化方法。反应通过促进[加入Pd（Cl）的（η 3 -C 3 H ^ 5）] 2和由环状硼酸盐的dehydroboration进行。通过使用环氧化物和现成的二-B（pin）-甲烷（pin =频哪醇），可以制备一系列含烯丙基醇的烯基硼酸酯，包括那些含有叔醇的硼酸烯基硼酸酯，其收率可达75％。 > 20：1 é / ž。

  DOI：

  10.1021/acs.orglett.7b03853

文献信息

• Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes
  作者：Mingbing Zhong、Yohann Gagné、Taylor O. Hope、Xavier Pannecoucke、Mathieu Frenette、Philippe Jubault、Thomas Poisson

  DOI：10.1002/anie.202101874

  日期：2021.6.21

  photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions

  报道了烯烃和炔烃的光催化硼氢化反应。使用新设计的铜光催化剂和 B 2 Pin 2可以形成硼基自由基，该自由基可用于大量烯烃和炔烃的硼氢化反应。硼氢化产物以高产率分离，在温和条件下具有优异的非对映选择性和高官能团耐受性。硼氢化反应是在连续流动条件下开发的，以证明其合成效用。研究了反应机理，并提出了原位形成的硼酸盐和处于激发态的铜光催化剂之间的氧化反应，以形成硼基自由基。
• Ligand-free hydroboration of alkynes catalyzed by heterogeneous copper powder with high efficiency
  作者：Jie Zhao、Zhiqiang Niu、Hua Fu、Yadong Li

  DOI：10.1039/c3cc48670b

  日期：——

  Regioselective hydroboration of terminal and internal alkynes is realized by using copper powder (0.3–1 μm) as a catalyst without any ligand.

  端基和内部炔烃的区域选择性氢硼化反应是通过使用铜粉（0.3-1μm）作为催化剂而实现的，而无需任何配体。
• Efficient heterogeneous hydroboration of alkynes: enhancing the catalytic activity by Cu(0) incorporated CuFe₂O₄ nanoparticles
  作者：Xianghua Zeng、Chunhua Gong、Haiyang Guo、Hao Xu、Junyong Zhang、Jingli Xie

  DOI：10.1039/c8nj03708f

  日期：——

  Nano-copper ferrite supported Cu catalysts are active for hydroboration of alkynes to vinylboronates.

  纳米铜铁氧体负载的铜催化剂对炔烃的氢硼化反应具有活性，生成乙烯硼酸酯。
• Cs ₄ B ₄ O ₃ F ₁₀ : First Fluorooxoborate with [BF ₄ ] Involving Heteroanionic Units and Extremely Low Melting Point
  作者：Ming Xia、Miriding Mutailipu、Fuming Li、Zhihua Yang、Shilie Pan

  DOI：10.1002/chem.202101321

  日期：2021.7.7

  Herein, a new congruently melting mixed-anion compound Cs4B4O3F10 has been characterized as the first fluorooxoborate with [BF4] involving heteroanionic units. Compound Cs4B4O3F10 possesses two highly fluorinated anionic clusters and therefore its formula can be expressed as Cs3(B3O3F6) ⋅ Cs(BF4). The influence of [BF4] units on micro-symmetry and structural evolution was discussed based on the parent

  在此，一种新的同熔混合阴离子化合物 Cs 4 B 4 O 3 F 10已被表征为第一个具有 [BF 4 ] 的含杂阴离子单元的氟代硼酸盐。化合物Cs 4 B 4 O 3 F 10具有两个高度氟化的阴离子簇，因此其分子式可以表示为Cs 3 (B 3 O 3 F 6 ) ⋅ Cs(BF 4 )。基于母体化合物讨论了[BF 4 ]单元对微对称性和结构演化的影响。更重要的是，Cs 4B 4 O 3 F 10在所有可用的硼酸盐中显示出最低的熔点，从而为此类系统创造了新的记录。这项工作对于使用全氟化 [BF 4 ] 单元丰富和定制硼酸盐的结构具有重要意义。
• Electrochemical Hydroboration of Alkynes
  作者：Maude Aelterman、Morgane Sayes、Philippe Jubault、Thomas Poisson

  DOI：10.1002/chem.202101132

  日期：2021.6.4

  Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This

  在此，我们报道了使用 B 2 Pin 2作为硼源的炔烃的电化学硼氢化反应。这种前所未有的反应歧管适用于广泛的炔烃，无需金属催化剂或氢化物源，即可使硼氢化产物具有良好的收率。这种转变依赖于原位形成的硼酸盐可能的电化学氧化。这种在未分开的电池中进行的阳极氧化允许形成推定的硼基自由基，该自由基与炔烃发生反应。