Alpha-(二甲基氯化硅烷)异丙苯 | 118740-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Alpha-(二甲基氯化硅烷)异丙苯
• 中文别名: Α-(氯代二甲硅基)枯烯
• 英文名称: chloro(α,α-dimethylbenzyl)dimethylsilane
• 英文别名: (1-methyl-1-phenylethyl)(dimethyl)chlorosilane；cumyldimethylsilyl chloride；chlorocumyldimethylsilane；dimethyl(phenyl dimethyl carbinyl)chlorosilane；Chlorodimethyl(2-phenylpropan-2-yl)silane；chloro-dimethyl-(2-phenylpropan-2-yl)silane
• CAS: 118740-38-8
• 化学式: C₁₁H₁₇ClSi
• mdl: MFCD00143579
• 分子量: 212.794
• InChiKey: SUMFNCSNBLYOEK-UHFFFAOYSA-N

物化性质

• 密度：
  1,01 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  Alpha-(二甲基氯化硅烷)异丙苯 在 N-甲基吗啉 、 硝酸铵 、 氢氧化钾 、 草酰氯 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 三氟乙酸酐 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.33h， 生成 N-(9-fluorenylmethoxycarbonyl)-O-[(4-amino-α,α-dimethylbenzyl)dimethylsilyl]-L-serine allyl ester
  参考文献：
  名称：

  A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis

  摘要：

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00649-3
• 作为产物：
  描述：

  二氯二甲基硅烷 、 ALFA, ALFA-二甲基苄氯 生成 Alpha-(二甲基氯化硅烷)异丙苯
  参考文献：
  名称：

  ISIXARA, TOSINOBU;TAKAMIDZAVA, MINORU;EHNDO, MIKIO;KUBOTA, TORU

  摘要：

  DOI：

文献信息

• Zinc Mediated Reactions in Organic Synthesis: Efficient Synthesis of Silyl Ethers under Mild Conditions
  作者：Babasaheb Pandurang Bandgar、Satish Navnath Chavare、Shivaji Sandu Pandit

  DOI：10.1002/jccs.200500019

  日期：2005.2

  General and practical method for the synthesis of silyl ethers in the presence of zinc powder under mild conditions has been described.

  描述了在温和条件下在锌粉存在下合成甲硅烷基醚的一般实用方法。
• Total synthesis of buergerinin F via effective construction of the asymmetric quaternary carbons using an enantioselective aldol reaction
  作者：Isamu Shiina、Yo-ichi Kawakita、Ryoutarou Ibuka、Kazutoshi Yokoyama、Yu-suke Yamai

  DOI：10.1039/b507401k

  日期：——

  An efficient method for the synthesis of (+)-buergerinin F is established via the enantioselective aldol reaction of a tetra-substituted ketene silyl acetal with crotonaldehyde, followed by intramolecular Wacker-type ketalization.

  一种有效的合成（+）-buergerinin F的方法是通过四取代的烯酮甲硅烷基乙缩醛与巴豆醛的对映选择性羟醛反应，然后进行分子内Wacker型缩酮化反应来建立的。
• Construction of AB-Ring System of Taxane Framework by A-Ring Annulation Strategy: Synthesis of 1-Hydroxy-8,11,11-trimethylbicyclo-(5.3.1)undec-7-en-9-one by Way of Intramolecular Aldol Cyclization to Form the C1-C10 Bond.
  作者：Koji YAMADA、Hayato IWADARE、Teruaki MUKAIYAMA

  DOI：10.1248/cpb.45.1898

  日期：——

  Construction of the AB-ring system of the taxane framework via an A-ring annulation strategy was demonstrated by base-mediated intramolecular aldol reaction of (Z)-2,2-dimethyl-3-(1-methyl-2-oxopropylidene)cyclooctanone, affording the title compound, 1-hydroxy-8,11,11-trimethylbicyclo[5.3.1]undec-7-en-9-one. A cyclization precursor, the tetra-substituted (Z)-alkene, was prepared from the corresponding

  通过碱介导的（Z）-2,2-二甲基-3-（1-甲基-2-氧代亚丙基）环辛酮的分子内醇醛缩合反应，证明了通过A环环化策略构建紫杉烷骨架的AB环系统。得到标题化合物1-羟基-8,11,11-三甲基双环[5.3.1] undec-7-en-9-one。由相应的环辛酮衍生物3-[（α，α-二甲基苄基）二甲基甲硅烷氧基] -2,2-二甲基环辛酮经双环α，β-不饱和内酯中间体制备环化前体四取代的（Z）-烯烃。
• Synthesis of AB Ring Model System of Taxol<i>via</i>Allylation of 8-Membered Ring Compound and Intramolecular Aldol Condensation
  作者：Teruaki Mukaiyama、Isamu Shiina、Kaname Kimura、Yuji Akiyama、Hayato Iwadare

  DOI：10.1246/cl.1995.229

  日期：1995.3

  1-t-Butyldimethylsiloxy-8,11,11-trimethylbicyclo[5.3.1]undec-7-en-9-one (2) has been synthesized via intramolecular aldol condensation of the precursor 3 by combined use of lithium diisopropylamide (LDA) and CeCl3. The dicarbonyl compound 3 was prepared by allylation of 8-membered ring ketone 6b.

  1-t-丁基二甲基甲硅烷氧基-8,11,11-三甲基双环[5.3.1]undec-7-en-9-one (2) 已通过前体 3 的分子内醛醇缩合合成了二异丙基氨基锂 (LDA)和 CeCl3。二羰基化合物3通过8元环酮6b的烯丙基化制备。
• Stereoselective Synthesis of Highly Substituted γ-Lactams by the [3+2] Annulation of α-Siloxy Allylic Silanes with Chlorosulfonyl Isocyanate
  作者：Antonio Romero、K. A. Woerpel

  DOI：10.1021/ol060596g

  日期：2006.5.1

  A stereoselective synthesis of gamma-lactams by the [3+2] annulation of alpha-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted gamma-lactams. Oxidation of the silyl group afforded access to complex beta-hydroxy-gamma-lactams.

表征谱图