(cyclopentyloxy)dimethyl(phenyl)silane | 263561-00-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (cyclopentyloxy)dimethyl(phenyl)silane
• 英文别名: Cyclopentyloxy-dimethyl-phenylsilane；cyclopentyloxy-dimethyl-phenylsilane
• CAS: 263561-00-8
• 化学式: C₁₃H₂₀OSi
• 分子量: 220.387
• InChiKey: QWXKUQBEGSOSFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环戊醇 、 二甲基苯基硅烷 在 tris(2,2'-bipyridyl)ruthenium dichloride 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以83%的产率得到(cyclopentyloxy)dimethyl(phenyl)silane
  参考文献：
  名称：

  硅烷与醇和水的光催化交叉脱氢偶联

  摘要：

  开发了一种在光催化下硅烷与醇脱氢偶联的有效方法。反应在室温下在乙腈中在可见光照射下，在Ru（bpy）3 Cl 2（0.5mol％）的存在下进行。所开发的方法学也适用于以水为偶联剂的硅烷醇的合成。

  DOI：

  10.1039/d1cc00129a

文献信息

• Photocatalyzed cross-dehydrogenative coupling of silanes with alcohols and water
  作者：Haiping Lv、Ronibala Devi Laishram、Jingchao Chen、Ruhima Khan、Yuanbin Zhu、Shiyuan Wu、Jianqiang Zhang、Xingyuan Liu、Baomin Fan

  DOI：10.1039/d1cc00129a

  日期：——

  An efficient method for the dehydrogenative coupling of silanes with alcohols under photocatalysis was developed. The reaction proceeded in the presence of Ru(bpy)3Cl2 (0.5 mol%) under visible light irradiation in acetonitrile at room temperature. The developed methodology was also applicable for the synthesis of silanols using water as a coupling partner.

  开发了一种在光催化下硅烷与醇脱氢偶联的有效方法。反应在室温下在乙腈中在可见光照射下，在Ru（bpy）3 Cl 2（0.5mol％）的存在下进行。所开发的方法学也适用于以水为偶联剂的硅烷醇的合成。
• Homobimetallic Rhodium NHC Complexes as Versatile Catalysts for Hydrosilylation of a Multitude of Substrates in the Presence of Ambient Air
  作者：Aron J. Huckaba、T. Keith Hollis、Sean W. Reilly

  DOI：10.1021/om400452q

  日期：2013.11.11

  di-Rh complexes based on 1,3-bis(3′-butylbenzimidazol-2′-ylidene)benzene were utilized as catalysts for hydrosilylation. Among the substrates investigated were aldehydes, ketones, α,β-unsaturated carbonyls, acyl chlorides, nitriles, alkenes, nitro groups, isocyanates, and tertiary amides. Additionally, carbon dioxide underwent hydrosilylation to produce dimethylphenylsilylformate. The catalysts compared

  最近报道的两种基于1,3-双（3'-丁基苯并咪唑-2'-亚烷基）苯的空气和水稳定的di-Rh络合物被用作氢化硅烷化的催化剂。所研究的底物包括醛，酮，α，β-不饱和羰基，酰氯，腈，烯烃，硝基，异氰酸酯和叔酰胺。另外，使二氧化碳进行氢化硅烷化以产生二甲基苯基甲硅烷基甲酸酯。该催化剂与其他先前报道的氢化硅烷化催化剂相比具有很好的对比，并且在每种情况下，Rh–Cl催化剂都比Rh–I络合物更快，更具选择性。
• An Efficient Solvent-Free Route to Silyl Esters and Silyl Ethers
  作者：Yuko Ojima、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1002/adsc.200900230

  日期：2009.6

  Abstractmagnified imageDinuclear metal complexes, especially (p‐cymene)ruthenium dichloride dimer [RuCl2(p‐cymene)]2}, have been found to exhibit high catalytic performance for the dehydrosilylation of various kinds of carboxylic acids and alcohols. The dehydrosilylation with [RuCl2(p‐cymene)]2 proceeded efficiently with only one equivalent of silane with respect to substrate (carboxylic acids or alcohols) under solvent‐free conditions to give the corresponding silyl esters and ethers in excellent yields with a high turnover number (TON) and frequency (TOF). The 1H NMR spectrum of a toluene‐d8 solution of [RuCl2(p‐cymene)]2 and a silane showed a signal assignable to the ruthenium hydride species. In contrast, no new signals were detected in the 1H NMR spectrum of a toluene‐d8 solution of [RuCl2(p‐cymene)]2 and a carboxylic acid or an alcohol. Therefore, the ruthenium metal in [RuCl2(p‐cymene)]2 activates a silane to afford the hydride intermediate, possibly a silylmetal hydride species. Then, the nucleophilic attack of a substrate (carboxylic acid or alcohol) to the hydride intermediate proceeds to give the corresponding silylated product. The present dehydrosilylation with an optically active silane proceeded exclusively under inversion of stereochemistry at the chiral silicon center, suggesting that the nucleophilic attack of a substrate to the hydride intermediate occurs from the backside of the ruthenium‐silicon bond.
• Nitrogen-Neighbored Single-Cobalt Sites Enable Heterogeneous Oxidase-Type Catalysis
  作者：Qi Zhang、Mi Peng、Zirui Gao、Wendi Guo、Zehui Sun、Yi Zhao、Wu Zhou、Meng Wang、Bingbao Mei、Xian-Long Du、Zheng Jiang、Wei Sun、Chao Liu、Yifeng Zhu、Yong-Mei Liu、He-Yong He、Zhen Hua Li、Ding Ma、Yong Cao

  DOI：10.1021/jacs.2c12586

  日期：——