lithium B-1-octynyltriisopropylborate

• 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: lithium B-1-octynyltriisopropylborate
• 英文别名: Lithium;oct-1-ynyl-tri(propan-2-yloxy)boranuide
• 化学式: C₁₇H₃₄BO₃*Li
• 分子量: 304.207
• InChiKey: XGOZKPIPEAPFBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  lithium B-1-octynyltriisopropylborate 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.5h， 生成 (R)-N-(1-phenylnon-2-ynyl)acetamide
  参考文献：
  名称：

  Asymmetric Synthesis of Propargylamides via 3,3‘-Disubstituted Binaphthol-Modified Alkynylboronates

  摘要：

  Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.

  DOI：

  10.1021/ol0523087
• 作为产物：
  描述：

  硼酸三异丙酯 、 n-己基乙炔基锂 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 为溶剂， 反应 2.5h， 生成 lithium B-1-octynyltriisopropylborate
  参考文献：
  名称：

  乙炔衍生物就地生成的炔基硼酸酯的Suzuki-miyaura偶联

  摘要：

  报道了炔基硼酸酯（从炔属衍生物原位产生）与芳基溴化物或乙烯基溴化物之间的新的有效的Suzuki-Miyaura偶联反应。

  DOI：

  10.1021/ol006439d

文献信息

• An efficient synthesis of 2,3,5-trisubstituted furans from α,β-unsaturated ketones
  作者：Catherine D. Brown、J.Michael Chong、Lixin Shen

  DOI：10.1016/s0040-4020(99)00898-4

  日期：1999.12

  A simple, regioselective synthesis of 2,3,5-trisubstituted furans is described. Conjugate addition of alkynylboronates to α,β-unsaturated ketones, followed by acid-catalyzed cyclization of the resulting γ-alkynyl ketones affords trisubstituted furans in 31–97% overall yields.

  描述了2,3,5-三取代的呋喃的简单的区域选择性合成。将炔基硼酸酯加成到α，β-不饱和酮上，然后酸催化环化所得的γ-炔基酮，可得到三取代呋喃，总产率为31-97％。
• Asymmetric Conjugate Addition of Alkynylboronates to Enones
  作者：J. Michael Chong、Lixin Shen、Nicholas J. Taylor

  DOI：10.1021/ja992922b

  日期：2000.3.1
• Ligand-Catalyzed Asymmetric Alkynylboration of Enones:  A New Paradigm for Asymmetric Synthesis Using Organoboranes
  作者：T. Robert Wu、J. Michael Chong

  DOI：10.1021/ja043001q

  日期：2005.3.1

  Asymmetric conjugate alkynylation of enones may be effected using a B-1-alkynyldiisopropylboronate and catalytic amounts of binaphthol ligands. The high enantioselectivities observed are comparable to those obtained using stoichiometric amounts of binaphthol-modified boronate reagents, suggesting that this is a ligand-accelerated process. This is the first demonstration that catalytic amounts of chiral diols can be used with boronates to effect high levels of stereochemical control.
• Suzuki−Miyaura Coupling of Alkynylboronic Esters Generated in Situ from Acetylenic Derivatives
  作者：Anne-Sophie Castanet、Françoise Colobert、Thierry Schlama

  DOI：10.1021/ol006439d

  日期：2000.11.1

  A new effective Suzuki-Miyaura coupling reaction between alkynylboronic esters (generated in situ from acetylenic derivatives) and arylbromides or vinylbromides is reported.

  报道了炔基硼酸酯（从炔属衍生物原位产生）与芳基溴化物或乙烯基溴化物之间的新的有效的Suzuki-Miyaura偶联反应。
• Asymmetric Synthesis of Propargylamides via 3,3‘-Disubstituted Binaphthol-Modified Alkynylboronates
  作者：T. Robert Wu、J. Michael Chong

  DOI：10.1021/ol0523087

  日期：2006.1.1

  Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.