(+) α-naphthylphenylmethyl(menthyloxy)silane(-) | 35742-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+) α-naphthylphenylmethyl(menthyloxy)silane(-)
• 英文别名: (-) α-naphthylphenylmethyl(menthyloxy)silane(-)；(S)-(-)-[(-)-menthyloxy](1-naphthyl)methylphenylsilane；α-maphthylphenylmethyl-(-)-menthoxysilane；Methyl-1-naphthyl-phenylsilyl-<(-)-menthyloxid>；Methyl-1-naphthyl-phenylsilyl-((-)-menthyloxid)；{[(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl]oxy}(methyl)1-naphthyl(phenyl)silane；methyl-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-naphthalen-1-yl-phenylsilane
• CAS: 35742-37-1
• 化学式: C₂₇H₃₄OSi
• 分子量: 402.652
• InChiKey: CGJJTDPRCZQGHJ-OEWXUPOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+) α-naphthylphenylmethyl(menthyloxy)silane(-) 在 lithium aluminium tetrahydride 、 platinized ion-exchange resin AV-17-8 作用下， 以 二丁醚 为溶剂， 反应 18.0h， 生成 (+)α-naphthylphenylmethyloctylsilane
  参考文献：
  名称：

  Reikhsfel'd, V. O.; Flerova, N. I.; Filippov, N. A., Journal of general chemistry of the USSR, 1980, vol. 50, # 9, p. 1629 - 1633

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴代萘 在 magnesium 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 (+) α-naphthylphenylmethyl(menthyloxy)silane(-)
  参考文献：
  名称：

  中性反应条件下锰硅烷选择性氧化催化氢硅烷氧化成硅烷醇

  摘要：

  在中性反应条件下，用H 2 O 2进行的第一次锰催化的有机硅烷氧化为硅烷醇。可以耐受具有烷基，芳基，炔基和杂环取代基的多种有机硅烷，以及受阻位有机硅烷。氧化似乎是通过涉及氢过氧化锰物质的协同过程进行的。该方案具有温和的反应条件，快速的氧化作用，并且没有废副产物，可实现硅烷醇和硅烷二醇的低成本，生态友好的合成。

  DOI：

  10.1002/anie.201900342

文献信息

• 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.
• A Stereoselective Approach to Optically Active Bifunctional 1,3-Dimethyl-1,3-diphenyldisiloxanes
  作者：Motoi Oishi、Yusuke Kawakami

  DOI：10.1021/ol990068n

  日期：1999.8.1

  [GRAPHICS]Functionalized disiloxanes have attracted much attention as Versatile synthetic intermediates in the preparation of disiloxane containing polymers. In this report, a highly stereoselective (98% inversion) halogenating cleavage reaction of the silicon-naphthyl bond to obtain optically active (S,S)-1,3-dimethyl-1,3-diphenyldisiloxanediol ((S,S):(R,S):(R,R) = 86:14:0) was demonstrated.