1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octan-3-one | 1453867-90-7

• 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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octan-3-one
• 英文别名: 1-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)octan-3-one
• CAS: 1453867-90-7
• 化学式: C₁₄H₂₇BO₃
• 分子量: 254.178
• InChiKey: NOHAWFWLVBOTMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octan-3-one 在 sodium perborate monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以90%的产率得到1-羟基-3-辛酮
  参考文献：
  名称：

  Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations

  摘要：

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.

  DOI：

  10.1021/jo401293a
• 作为产物：
  描述：

  1-辛烯-3-酮 、 联硼酸频那醇酯 在 甲醇 、 copper nanoparticles on black carbon 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以80%的产率得到1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octan-3-one
  参考文献：
  名称：

  铜纳米粒子催化的温和条件下的α，β-不饱和酮的硼化和选择性还原

  摘要：

  设计了一种有效的合成铜纳米颗粒的策略，这些纳米颗粒在B 2（pin）2和α，β-不饱和酮的共轭添加中具有高催化活性。原脱硼的反应可以通过添加NaO t Bu来进行。以这种方式，开发了一种以有机硼烷为中间体，还原α，β-不饱和酮的共轭烯烃的新方法。Cu纳米晶体在克级反应和循环利用实验中也具有优异的性能。提出了一种可能的机制。

  DOI：

  10.1016/j.tet.2016.07.079

文献信息

• Borylation and selective reduction of α,β-unsaturated ketones under mild conditions catalyzed by Cu nanoparticles
  作者：Xin-Feng Zhou、Yu-Yang Sun、Ya-Dong Wu、Jian-Jun Dai、Jun Xu、Yu Huang、Hua-Jian Xu

  DOI：10.1016/j.tet.2016.07.079

  日期：2016.9

  An effective strategy for synthesis of Cu nanoparticles is designed, these nanoparticles have high catalytic activity in conjugate addition of B2(pin)2 and α,β-unsaturated ketones. The reaction of protodeboration can proceed with adding NaOtBu. In this way, a new method to reduce the conjugated alkenes of α,β-unsaturated ketones is developed with organoboranes as intermediates. Cu nanocrystals also

  设计了一种有效的合成铜纳米颗粒的策略，这些纳米颗粒在B 2（pin）2和α，β-不饱和酮的共轭添加中具有高催化活性。原脱硼的反应可以通过添加NaO t Bu来进行。以这种方式，开发了一种以有机硼烷为中间体，还原α，β-不饱和酮的共轭烯烃的新方法。Cu纳米晶体在克级反应和循环利用实验中也具有优异的性能。提出了一种可能的机制。
• Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations
  作者：Casey Medina、Kyle P. Carter、Michael Miller、Timothy B. Clark、Gregory W. O’Neil

  DOI：10.1021/jo401293a

  日期：2013.9.20

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.