3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cycloheptan-1-one | 350498-94-1

• 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: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cycloheptan-1-one
• 英文别名: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-cycloheptanone；3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cycloheptanone；O(C7H11)(pinacolatoboron)；O(C7H11)Bpin；Cycloheptanone, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• CAS: 350498-94-1
• 化学式: C₁₃H₂₃BO₃
• 分子量: 238.135
• InChiKey: OBKJEEXUXXCBDA-UHFFFAOYSA-N

物化性质

• 沸点：
  303.6±35.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cycloheptan-1-one 在 ammonium carbonate 、 盐酸 、 水 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 1-amino-3-borono-cycloheptanecarboxylic acid
  参考文献：
  名称：

  Synthesis of novel boron containing unnatural cyclic amino acids as potential therapeutic agents

  摘要：

  Two boronated alpha -amino acids, 1-amino-3-boronocyclopentanecarboxylic acid and 1-amino-3-boronocycloheptanecarboxylic acid were prepared. The key step in the syntheses was the 1,4-boration of the alpha,beta -unsaturated cyclic ketones using the bis-pinacolatodiboron ester to generate the boronated ketones which were then converted to the corresponding amino acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01486-1
• 作为产物：
  描述：

  2-环庚烯-1-酮 、 联硼酸频那醇酯 在 四(三苯基膦)铂 作用下， 以 甲苯 为溶剂， 以86%的产率得到3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cycloheptan-1-one
  参考文献：
  名称：

  双（频哪醇）二硼烷（4）与羰基烯酮的加成反应和（频哪醇）2 BCH 2 B和（频哪醇）2 BCH 2 CH 2 B的插入和偶联反应

  摘要：

  标题化合物加成α，β-不饱和羰基后，中间体硼烯酸酯水解后得到1,4-加成产物，分离产率为68-86％（四个实例）。此外，我们发现用双（频哪醇合），该重氮甲烷进行反应，以乙硼烷插入亚甲基，得到（频哪醇）2 BCH 2产率为83％乙。另一种合成方法是将（频哪醇）BCH 2 I与各种金属偶联。

  DOI：

  10.1021/om010282r

文献信息

• Catalytic enantioselective boron conjugate addition to cyclic carbonyl compounds: a new approach to cyclic β-hydroxy carbonyls
  作者：Xinhui Feng、Jaesook Yun

  DOI：10.1039/b914207j

  日期：——

  The highly enantioselective conjugate boration of six-membered and seven-membered cyclic enones and unsaturated esters was achieved by the use of a copper-(R,S)-Taniaphos complex with up to 99% ee under optimal conditions.

  六元和七元环状烯酮和不饱和酯的高对映选择性共轭硼酸盐是通过在最佳条件下使用铜-（R，S）-他尼磷配合物和高达99％ee来实现的。
• β-Boration of α,β-unsaturated carbonyl compounds in ethanol and methanol catalyzed by CCC-NHC pincer Rh complexes
  作者：Sean W. Reilly、Gopalakrishna Akurathi、Hannah K. Box、Henry U. Valle、T. Keith Hollis、Charles Edwin Webster

  DOI：10.1016/j.jorganchem.2015.11.010

  日期：2016.1

  Quantitative beta-boration of alpha, beta-unsaturated carbonyl compounds was achieved utilizing the eco-friendly solvent EtOH along with MeOH at room temperature in 1 h, by a CCC-NHC pincer Rh complex mixture. Substrates with beta-substituents were successfully converted yielding challenging, quaternary C-B bonds. The air-and water-stable pre-catalyst A, identified as a mixture of iodo and chloro CCC-NHC pincer Rh amine complexes, was evaluated for catalytic activity. This report is the first example of a pincer Rh complex demonstrating catalytic activity in a 1,4-addition at room temperature. (C) 2015 Elsevier B.V. All rights reserved.
• Lee, Kang-sang; Zhugralin, Adil R.; Hoveyda, Amir H., Journal of the American Chemical Society, 2009, vol. 131, p. 7253 - 7255
  作者：Lee, Kang-sang、Zhugralin, Adil R.、Hoveyda, Amir H.

  DOI：——

  日期：——
• Rhodium-catalyzed 1,4-addition reactions of diboron reagents to electron deficient olefins
  作者：George W. Kabalka、Bhaskar C. Das、Sasmita Das

  DOI：10.1016/s0040-4039(02)00261-7

  日期：2002.3

  The 1,4-addition of bis(pinacolato)diboron and bis(neopentyl glycolato)diboron to alpha,beta-unsaturated ketones, esters, nitriles, and aldehydes was developed using a rhodium catalyst. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A borylcopper species generated from bis(pinacolato)diboron and its additions to α,β-unsaturated carbonyl compounds and terminal alkynes
  作者：Kou Takahashi、Tatsuo Ishiyama、Norio Miyaura

  DOI：10.1016/s0022-328x(00)00826-3

  日期：2001.4

  The addition of bis(pinacolato)diboron [(Me2C2O2)B-B(O2C2Me4)] to alpha,beta -unsaturated carbonyl compounds giving beta -boryl carbonyl compounds and the addition to terminal alkynes yielding either 2-boryl-1-alkenes or 1-boryl-1-alkenes were carried out in DMF at room temperature in the presence of CuCl and AcOK. The transmetalation between diboron and [Cu(CI)OAc]K generating a borylcopper species was proposed as the key step in the reactions because CuOAc similarly mediated both addition reactions to enones and alkynes in the presence of LiCl. (C) 2001 Elsevier Science B.V. All rights reserved.