2-Hex-1-ynyl-5,5-dimethyl-[1,3,2]dioxaborinane | 174584-79-3

• 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: 2-Hex-1-ynyl-5,5-dimethyl-[1,3,2]dioxaborinane
• 英文别名: 2-Hex-1-yn-1-yl-5,5-dimethyl-1,3,2-dioxaborinane；2-hex-1-ynyl-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 174584-79-3
• 化学式: C₁₁H₁₉BO₂
• 分子量: 194.082
• InChiKey: KRHBXNGXZSXLCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Hex-1-ynyl-5,5-dimethyl-[1,3,2]dioxaborinane 在 sodium hydroxide 、 正丁基锂 、 双氧水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-Butyl-((1S,7R,8S)-8-hex-1-ynyl-bicyclo[5.1.0]oct-8-yloxy)-dimethyl-silane
  参考文献：
  名称：

  1-（1-炔基）环丙醇通过其六羰基二钴配合物重排为 2-环戊烯酮。炔-Co2(CO)6配合物在有机合成中的新用途

  摘要：

  1-(1-炔基) 环丙醇向 2-环戊烯-1-酮的新重排是在其炔基部分与八羰基二钴 (Co2(CO8)) 络合后进行的。1-(1-炔基) 环丙醇在其炔烃末端具有广泛的取代基，以良好的产率重排为相应的 3-取代的 2-环戊烯-1-酮。In case of the reactions of 1-alkynylcyclopropanols with an alkyl substituent on the cyclopropane ring, either 4-substituted or 5-substituted 2-cyclopenten-1-ones could be selectively obtained by appropriate choice of stereochemistry and protective group of the substrates. 这种重排成功地应用于环戊烯酮环化成环烯烃的反应。根据

  DOI：

  10.1021/ja9734004
• 作为产物：
  描述：

  2, 2, 5, 5, 8, 8-hexamethyl-3, 7-dioxa-2, 8-disilanonane 、 钾三氟(1-己炔-1-基)硼酸酯(1-) 在 三甲基氯硅烷 作用下， 以 丙酮 为溶剂， 生成 2-Hex-1-ynyl-5,5-dimethyl-[1,3,2]dioxaborinane
  参考文献：
  名称：

  Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates

  摘要：

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.068

文献信息

• Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates
  作者：Yoshihiko Yamamoto、Kozo Hattori、Jun-ichi Ishii、Hisao Nishiyama

  DOI：10.1016/j.tet.2006.02.068

  日期：2006.5

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.
• Rearrangement of 1-(1-Alkynyl)cyclopropanols to 2-Cyclopentenones via Their Hexacarbonyldicobalt Complexes. A New Use of Alkyne−Co₂(CO)₆ Complexes in Organic Synthesis
  作者：Nobuharu Iwasawa、Takeshi Matsuo、Mari Iwamoto、Taketo Ikeno

  DOI：10.1021/ja9734004

  日期：1998.4.1

  protective group of the substrates. This rearrangement was successfully applied to cyclopentenone annulation reactions onto cycloalkenes. An efficient synthesis of alkynyl-substituted bicyclo[n.1.0]alkanol derivatives from the corresponding cycloalkenes according to Danheiser's protocol was developed, and bicyclic cyclopentenones were obtained in moderate to good yield by applying to these the cobalt-mediated

  1-(1-炔基) 环丙醇向 2-环戊烯-1-酮的新重排是在其炔基部分与八羰基二钴 (Co2(CO8)) 络合后进行的。1-(1-炔基) 环丙醇在其炔烃末端具有广泛的取代基，以良好的产率重排为相应的 3-取代的 2-环戊烯-1-酮。In case of the reactions of 1-alkynylcyclopropanols with an alkyl substituent on the cyclopropane ring, either 4-substituted or 5-substituted 2-cyclopenten-1-ones could be selectively obtained by appropriate choice of stereochemistry and protective group of the substrates. 这种重排成功地应用于环戊烯酮环化成环烯烃的反应。根据

表征谱图