cis-1,2-bis-(trimethylsiloxy)cyclopentane | 41235-26-1

• 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-(trimethylsiloxy)cyclopentane
• 英文别名: trimethyl-[(1R,2S)-2-trimethylsilyloxycyclopentyl]oxysilane
• CAS: 41235-26-1
• 化学式: C₁₁H₂₆O₂Si₂
• 分子量: 246.497
• InChiKey: HQUPRGSFHVWCBM-PHIMTYICSA-N

物化性质

• 沸点：
  225.4±33.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  15
• 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-(trimethylsiloxy)cyclopentane 在 三氟甲磺酸三甲基硅酯 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 2-[(1R,2S,5R)-1-[(1R,2S)-2-hydroxycyclopentyl]oxy-5-methyl-2-propan-2-ylcyclohexyl]-1-phenylethanone
  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-cyclopentanediol 、 六甲基二硅氮烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 cis-1,2-bis-(trimethylsiloxy)cyclopentane
  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

文献信息

• Piers’ borane-mediated hydrosilylation of epoxides and cyclic ethers
  作者：Jianbo Zhang、Sehoon Park、Sukbok Chang

  DOI：10.1039/c8cc03741h

  日期：——

  diarylborane-catalysed hydrosilylation of epoxides and cyclic ethers. Mechanistic studies on the in situ generated Piers’ borane (C6F5)2BH with hydrosilanes in the presence of an epoxide revealed that an alkyloxy(diaryl)borane (C6F5)2BOR is readily formed as a catalytically competent species for the outer-sphere hydrosilylation of epoxides and cyclic ethers.

  我们报道了环氧化物和环醚的第一个二芳基硼烷催化的氢化硅烷化反应。在环氧化物存在下与氢硅烷原位生成Piers's硼烷（C 6 F 5）2 BH的机理研究表明，烷氧基（二芳基）硼烷（C 6 F 5）2 BOR易于形成为催化活性物质用于环氧化物和环醚的外球氢化硅烷化。
• 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。
• A novel asymmetric desymmetrisation of meso-cyclopentane-1,2-diol via diasteroselective β-elimination of chiral α-arylsulfinyl acetals
  作者：Naoyoshi Maezaki、Motohiro Soejima、Miwako Takeda、Atsunobu Sakamoto、Tetsuaki Tanaka、Chuzo Iwata

  DOI：10.1039/c39940001345

  日期：——

  meso-Cyclopentane-1,2-diol was differentiated via diasteroselective C–O bond fission of the acetal utilising the anion stabilised by a neighbouring chiral sulfinyl group to provide the chiral alcohol.

  内消旋-环戊烷-1,2-二醇通过缩醛的非对映选择性C-O键裂变来区分，利用相邻的手性亚磺酰基稳定的阴离子提供手性醇。
• Multidentate Lewis acids. Adducts of monodentate and bidentate titanium trichloroalkoxides with ketones
  作者：Benoit Bachand、James D. Wuest

  DOI：10.1021/om00052a058

  日期：1991.6

  Like TiCl4, titanium trichloroisopropoxide (4) is a strong Lewis acid able to form 1:2 adducts with ketones. Low-temperature H-1 and C-13 NMR spectra indicate that these adducts adopt a mer octahedral geometry. Exchange of free and bound pinacolone occurs by a dissociative mechanism with DELTA-G double-ended-dagger 219 = 9.2 kcal/mol. Potentially bidentate titanium trichloroalkoxides 19-21 can be prepared by treating the bis(trimethylsilyl) ethers of trans-1,2-cyclohexanediols with 2 equiv of TiCl4. Compounds 19-21 form crystalline 1:2 ketone adducts even in the presence of excess ketone. An X-ray crystallographic study has shown that the close proximity of the OTiCl3 groups favors symmetric adducts 30 (X = Cl) with bridging chlorides, not adducts 31 with bridging, doubly activated carbonyl groups. Similar chloride-bridged structures are adopted in solution. Low-temperature H-1 and C-13 NMR spectra establish that unsymmetric 1:3 adducts 36 (X = Cl) are formed in solution in the presence of additional ketone. Symmetrization of the 1:3 pinacolone complex derived from bidentate titanium trichloroalkoxide 21 occurs by a normal dissociative mechanism with DELTA-G double-ended-dagger 223 = 10.4 kcal/mol. Since this process is slower than exchange in 1:2 adducts of monodentate analogue 4, symmetric intermediates or transition states 38 (X = Cl) with a single bridging carbonyl oxygen do not offer a low-energy intramolecular pathway for exchange. Slow exchange in the 1:3 adduct provides evidence that the two OTiCl3 groups in compounds 19-21 cooperate by forming a single chloride bridge that enhances the Lewis acidity of one site at the expense of the other.
• Ligand-Modified Catalysts for the McMurry Pinacol Reaction
  作者：Timothy A. Lipski、Mark A. Hilfiker、Scott G. Nelson

  DOI：10.1021/jo970792o

  日期：1997.7.1