cis-1,2-bis(trimethylsilyloxy)cyclohexane | 39789-20-3

• 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: cis-1,2-bis(trimethylsilyloxy)cyclohexane
• 英文别名: cis-1,2-bis-(trimethylsiloxy)cyclohexane；cis-1,2-bis(trimethylsiloxy)cyclohexane；cis-1,2-Bis-trimethylsilyloxy-cyclohexan；trimethyl-[(1R,2S)-2-trimethylsilyloxycyclohexyl]oxysilane
• CAS: 39789-20-3
• 化学式: C₁₂H₂₈O₂Si₂
• 分子量: 260.524
• InChiKey: XQTPMHWHLDRJLV-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  cis-1,2-bis(trimethylsilyloxy)cyclohexane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 (2r,2'S,3aR,5'R,7aS)-2'-isopropyl-5'-methylhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]
  参考文献：
  名称：

  Enantiodifferentiating functionalization of cis-cycloalkane-1,2-diols and cis-endo-5-norbornen-2,3-ylenebis(methanol) via chiral spiroacetals derived from L-menthone

  摘要：

  DOI：

  10.1021/jo00272a027
• 作为产物：
  描述：

  cis-1,2-cyclohexane 生成 cis-1,2-bis(trimethylsilyloxy)cyclohexane
  参考文献：
  名称：

  FACILE SYNTHESIS OF 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYLIDENE ACETALS USING TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE CATALYST

  摘要：

  醛和酮在三甲基硅基三氟甲磺酸盐催化剂存在下与烷氧基硅烷进行缩醛化反应，迅速生成相应的螺环邻醇酯和二-O-三甲基硅基-α-二醇。

  DOI：

  10.1246/cl.1981.375

文献信息

• Palladium-catalyzed silylation of alcohols with hexamethyldisilane
  作者：Eiji Shirakawa、Koji Hironaka、Hidehito Otsuka、Tamio Hayashi

  DOI：10.1039/b608958e

  日期：——

  The combination of hexamethyldisilane and a catalytic amount of [PdCl(η3-C3H5)]2–PPh3 was found to be effective for the trimethylsilylation of alcohols, where both of the two trimethylsilyl groups of hexamethyldisilane were transferred to alcohols without coproduction of any stoichiometric amount of byproduct but H2.

  发现使用催化量的[PdCl(η3-C3H5)]2–PPh3与六甲基二硅烷的组合对于醇的三甲基硅烷化反应非常有效，其中六甲基二硅烷的两个三甲基硅基团均转移至醇上，且不产生任何化学计量比的副产物，仅生成氢气。
• A new synthesis of 2,3,4,6-tetra-O-benzyl-d-glucopyranosylidene acetals, using trimethylsilyl trifluoromethanesulfonate as the catalyst
  作者：Shigeomi Horito、Katsuji Asano、Kazuyuki Umemura、Hironobu Hashimoto、Juji Yoshimura

  DOI：10.1016/0008-6215(83)84015-4

  日期：1983.9

  in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst. Application to cis - and trans -1,2-diols containing primary, secondary, and tertiary hydroxyl groups was examined, and a new rearrangement was found in the reaction of a d -glucono-1,5-lactone derivative having an acetyl group at O-6.

  摘要在苯甲酸存在下，将2,3,4,6-四-O-苄基-d-葡萄糖酸-1,5-内酯与双-O-（三甲基甲硅烷基）-1,2-二醇缩合合成标题化合物。三甲基甲硅烷基三氟甲磺酸盐为催化剂。考察了对含伯，仲和叔羟基的顺式和反式-1,2-二醇的应用，并发现在O处具有乙酰基的ad -glucono-1,5-lactone衍生物的反应中发生了新的重排。 -6。
• Novel asymmetric desymmetrization of meso-1,2-diols via diastereoselective β-elimination of chiral α-arylsulfinyl acetals
  作者：Maezaki Naoyoshi、Soejima Motohiro、Takeda Miwako、Sakamoto Atsunobu、Matsumori Yûki、Tanaka Tetsuaki、Iwata Chuzo

  DOI：10.1016/0040-4020(96)00294-3

  日期：1996.5

  Enantioselective desymmetrization of meso-1,2-diols was accomplished via diastereoselective CO bond fission of acetals derived from various optically active β-ketosulfoxides with high diastereoselectivities. The substituent at the γ-position of the β-ketosulfoxide plays an important role in this cleavage.

  的对映选择性desymmetrization内消旋-1,2-二醇被完成通过从各种光学活性的β-ketosulfoxides具有高非对映选择性衍生的缩醛的非对映选择性CO键断裂。β-酮亚砜的γ-位上的取代基在该裂解中起重要作用。
• 40. Aspects of stereochemistry. Part III. Acidic and basic hydrolysis of some diol cyclic sulphates and related compounds
  作者：J. S. Brimacombe、A. B. Foster、E. B. Hancock、W. G. Overend、M. Stacey

  DOI：10.1039/jr9600000201

  日期：——
• Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides
  作者：Alexander J. Cresswell、Stephen G. Davies、Aude L.A. Figuccia、Ai M. Fletcher、Dorus Heijnen、James A. Lee、Melloney J. Morris、Alice M.R. Kennett、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tetlet.2014.12.044

  日期：2015.6

  The incorporation of alkoxy ligands within a range of alkoxyfluoroboranes and dialkoxyfluoroboranes results in fluoroborane reagents with attenuated Lewis acidity and increased ability to donate fluoride ion(s) when compared to boron trifluoride itself. Pinacolatoboron fluoride (pinBF), prepared in situ from BF3 center dot OEt2 and bis(O-trimethylsilyl)pinacol, has been identified as an efficient fluoride donor which allows highly stereoselective S(N)1-type epoxide ring-opening (with retention of configuration) of a range of trans-beta-methyl-substituted aryl epoxides to give the corresponding syn-fluorohydrins. The substrate scope of this transformation is more broad than the analogous protocol using boron trifluoride alone. (C) 2014 Elsevier Ltd. All rights reserved.