2-[(Z)-1-diethoxyphosphoryl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 476156-61-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 2-[(Z)-1-diethoxyphosphoryl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 476156-61-3
• 化学式: C₂₂H₄₃B₂O₇P
• 分子量: 472.175
• InChiKey: GTFUDDCYWFGJFB-ISLYRVAYSA-N

物化性质

• 沸点：
  438.8±55.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(Z)-1-diethoxyphosphoryl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到[(Z)-1,2-Bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-1-enyl]-phosphonic acid
  参考文献：
  名称：

  基质金属蛋白酶 (MMP-2) 有机硼酸盐抑制剂

  摘要：

  合成了由 BB、BC (R1R2) B、BCCB、CBC、药用部 RBC = CBB 和 RBC = CBP 结构组成的新型有机硼酸酯衍生物，并已在体外作为 MMP-2 抑制剂进行了研究。我们发现大多数硼酸盐衍生物（不含磷的那些）对 MMP-2 显示出显着的活性。三硼酸盐 14 被证明是一种有效的 MMP-2 抑制剂，浓度为 5 和 10 μM。研究并讨论了化合物的构效关系 (SAR) 数据。

  DOI：

  10.1002/ardp.200300827
• 作为产物：
  描述：

  diethyl (hex-1-ynyl)phosphonate 、 联硼酸频那醇酯 在 四(三苯基膦)铂 作用下， 以 甲苯 为溶剂， 以82%的产率得到2-[(Z)-1-diethoxyphosphoryl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Platinum(0)-Catalyzed Diboration of Alkynylboronates and Alkynylphosphonates with Bis(pinacolato)diborane(4):  Molecular Structures of [((Me₄C₂O₂)B)(C₆H₅)CC(P(O)(OC₂H₅)₂)(B(O₂C₂Me₄))] and [((Me₄C₂O₂)B)(C₄H₉)CC(B(O₂C₂Me₄))₂]

  摘要：

  The platinum(0)-catalyzed diboration addition reaction of bis(pinacolato)diborane(4) [(Me4C2O2)BB(O2C2Me4), 1] with various 1-alkynylphosphonates and 1-alkynylboronates 3a-d gave the desired novel cis-1,2-diboronated vinylphosphonate and trisboronated alkene products 5a, 5b and 5c, 5d respectively, in high yields. No detectable amount of the desired trisboronated alkene products 5c and 5d were isolated when the alkynylboronate was immediately added to a toluene solution of the catalyst and bis(pinacolato)diborane(4) followed by stirring overnight at 80 degreesC. Under these conditions, cis-1,2-diboronated alkenes 6c and 6d were obtained in 100% conversion yields, Only after changing the reaction conditions were 5c and 5d obtained in high yields. Tli, structure and configuration of the: new compounds have been fully characterized by H-1 C-13, P-31 and B-11 NMR, GCMS elemental analysis, and single-crystal X-ray structure determination. The structure of 5d was found to be fully isomorphous to that of 5c, with the C6H5 ring located in place (and similarly disordered about the 2-fold symmetry axis) of the C4H9 residue; therefore the results of the diffraction analysis, crystal data, and details of. the structure I determination of 5a. are not, included.

  DOI：

  10.1021/om020334s