(S)-2-phenyl-3-tert-butyldimethylsilyloxypropanol | 171433-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-phenyl-3-tert-butyldimethylsilyloxypropanol
• 英文别名: (2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-phenylpropan-1-ol
• CAS: 171433-02-6
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: FIUJKDNEYKHOBV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-phenyl-3-tert-butyldimethylsilyloxypropanol 在 氨 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 25.4h， 生成 (R)-2-phenyl-3-hydroxypropylcarbamate
  参考文献：
  名称：

  A chemoenzymatic synthesis of both enantiomers of 2-phenyl-3-hydroxypropylcarbamate, a metabolite of felbamate

  摘要：

  PPL catalyzed desymmetrization of 2-phenyl-1,3-propanediol (3) was the key step in the chemoenzymatic synthesis of both enantiomers of 2-phenyl-3-hydroxypropylcarbamate (2). Unsuccessful attempts at enzyme catalyzed (PPL, Novo SP435) transcarbamoylation, aminolysis and ammonolysis are also described.

  DOI：

  10.1016/0957-4166(95)00222-b
• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 在 咪唑 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-2-phenyl-3-tert-butyldimethylsilyloxypropanol
  参考文献：
  名称：

  A chemoenzymatic synthesis of both enantiomers of 2-phenyl-3-hydroxypropylcarbamate, a metabolite of felbamate

  摘要：

  PPL catalyzed desymmetrization of 2-phenyl-1,3-propanediol (3) was the key step in the chemoenzymatic synthesis of both enantiomers of 2-phenyl-3-hydroxypropylcarbamate (2). Unsuccessful attempts at enzyme catalyzed (PPL, Novo SP435) transcarbamoylation, aminolysis and ammonolysis are also described.

  DOI：

  10.1016/0957-4166(95)00222-b

文献信息

• Enantioselective Acylation of 1,2- and 1,3-Diols Catalyzed by Aminophosphinite Derivatives of (1<i>S</i>,2<i>R</i>)-1-Amino-2-indanol
  作者：Hiroyuki Aida、Kouhei Mori、Yasuyuki Yamaguchi、Shinya Mizuta、Tomomi Moriyama、Iwao Yamamoto、Tetsuya Fujimoto

  DOI：10.1021/ol2033459

  日期：2012.2.3

  A phosphinite derivative that can be easily prepared in two steps from commercially available aminoindanol was found to be an effective catalyst for enantioselective acylation of diols. For the asymmetric desymmetrization of meso-1,2-diols, the corresponding monoester was obtained in up to 95% ee from the reaction in the presence of 5 mol % catalyst.

  发现可以容易地以两步法从市售的氨基茚满醇制备次膦酸酯衍生物是用于二醇的对映选择性酰化的有效催化剂。对于不对称desymmetrization内消旋- 1,2-二醇，在高达95％的ee值从5％（摩尔）催化剂的存在下反应，获得相应的单酯。
• New General Method for Regio- and Stereoselective Allylic Substitution with Aryl and Alkenyl Coppers Derived from Grignard Reagents
  作者：Yohei Kiyotsuka、Yuji Katayama、Hukum P. Acharya、Tomonori Hyodo、Yuichi Kobayashi

  DOI：10.1021/jo802426g

  日期：2009.3.6

  Allylic substitution with sp2-carbon reagents (aryl and alkenyl anions) was realized by using allylic picolinates and copper reagents derived from RMgBr and CuBr·Me2S to afford anti SN2′ products regio- and stereoselectively. Steric and electronic factors in the reagents and the size of the methylene substituents around the allylic moiety marginally affected the selectivity. The reaction system was

  通过使用烯丙基吡啶甲酸酯和衍生自RMgBr和CuBr·Me 2 S的铜试剂实现Sp 2-碳试剂（芳基和烯基阴离子）的烯丙基取代，可以在区域和立体选择性地提供抗S N 2'产物。试剂中的立体和电子因素以及烯丙基部分周围的亚甲基取代基的大小在一定程度上影响了选择性。该反应系统也与烷基试剂相容。此外，该取代被应用于四元中心的构建和（-）-倍半茶烯酚的合成。吸电子的C的吡啶基的性质和螯合（═ ö）-C 5 H ^ 4 Ñ到MgBr 2 发现原位产生的碳负责替代的高效率。
• Picolinoxy Group, a New Leaving Group for anti S_N2′ Selective Allylic Substitution with Aryl Anions Based on Grignard Reagents
  作者：Yohei Kiyotsuka、Hukum P. Acharya、Yuji Katayama、Tomonori Hyodo、Yuichi Kobayashi

  DOI：10.1021/ol800300x

  日期：2008.5.1

  The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr*Me2S. The substitution proceeds with anti SN2' pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained.

  发现吡咯啉氧基是被衍生自ArMgBr和CuBr * Me2S的芳基亲核试剂进行烯丙基取代的极其强大的离去基团。取代以抗SN2'途径和高手性转移进行。吡啶基的吸电子作用和与MgBr2的螯合可能是成功的源头。结果表明这些效果。
• Metallophthalocyanine complex, Cr(TBPC)OTf: an efficient, recyclable Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes
  作者：Kohji Suda、Shin-ichiro Nakajima、Yasumi Satoh、Toshikatsu Takanami

  DOI：10.1039/b820948k

  日期：——

  The metallophthalocyanine complex Cr(TBPC)OTf works as a highly efficient, recyclable Lewis acid catalyst for the regio- and stereoselective rearrangements of epoxides to aldehydes.

  金属酞菁配合物Cr（TBPC）OTf是高效，可回收的路易斯酸催化剂，用于环氧化物和立体选择性重排成醛。
• Highly Regio- and Stereoselective Rearrangement of Epoxides to Aldehydes Catalyzed by High-Valent Metalloporphyrin Complex, Cr(TPP)OTf
  作者：Kohji Suda、Taketoshi Kikkawa、Shin-ichiro Nakajima、Toshikatsu Takanami

  DOI：10.1021/ja047104k

  日期：2004.8.1

  characteristic Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes. This Cr(TPP)OTf-catalyzed reaction is an operationally simple and especially convenient method for synthesizing optically active beta-siloxy aldehydes from 2,3-epoxy silyl ethers which are readily available in enantiomerically enriched forms by the Sharpless epoxidation of allylic alcohols followed

  三氟甲磺酸铬 (III) 四苯基卟啉三氟甲磺酸盐 Cr(TPP)OTf 在环氧化物向醛的区域和立体选择性重排中作为一种有效且具有特征性的路易斯酸催化剂起作用。这种 Cr(TPP)OTf 催化的反应是一种操作简单且特别方便的方法，用于从 2,3-环氧甲硅烷基醚合成光学活性 β-甲硅烷氧基醛，这些乙丙醚​​很容易通过烯丙醇的 Sharpless 环氧化以富含对映体的形式获得硅烷化。