(R)-(+)-1-<(t-Buthyldimethylsilyl)oxy>-1-phenyl-2-propanone | 120390-78-5

• 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: (R)-(+)-1-<(t-Buthyldimethylsilyl)oxy>-1-phenyl-2-propanone
• 英文别名: (R)-(+)-1-<(t-butyldimethylsilyl)oxy>-1-phenyl-2-propanone；(R)-1-<(tert-butyldimethylsilyl)oxy>-1-phenyl-2-propanone；1-(tert-butyldimethylsilanyloxy)-1-phenylpropan-2-one；R-(+)-1-(tert-butyldimethylsilyloxy)-1-phenyl-2-propanone；R-(+)-1-(tert.butyldimethylsilyloxy)-1-phenyl-2-propanone；(R)-(+)-1-[(t-Buthyldimethylsilyl)oxy]-1-phenyl-2-propanone；(1R)-1-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-one
• CAS: 120390-78-5
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: URCNTBZJQUYYIV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯甲酰-1H-苯并三唑 、 (R)-(+)-1-<(t-Buthyldimethylsilyl)oxy>-1-phenyl-2-propanone 在 N,N-二异丙基乙胺 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到4-(tert-butyldimethylsilanyloxy)-1,4-diphenylbutane-1,3-dione
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Soft Enolization:  A Facile and Efficient Synthesis of 1,3-Diketones

  摘要：

  Ketones undergo soft enolate formation and acylation on treatment with MgBr2 center dot OE2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-Pfp esters, and, in these cases, is conducted with untreated, reagent-grade CH2Cl2 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.

  DOI：

  10.1021/ol701599v
• 作为产物：
  描述：

  (R)-(+)-苯乙醇腈 在 咪唑 、 硫酸 作用下， 反应 13.25h， 生成 (R)-(+)-1-<(t-Buthyldimethylsilyl)oxy>-1-phenyl-2-propanone
  参考文献：
  名称：

  光学活性氰醇和酰基糖苷的生物有机合成

  摘要：

  通过酶催化形成旋光性氰醇，然后进行羟基保护并与格氏试剂反应，以高收率获得了具有高光学纯度的手性酰氯。

  DOI：

  10.1016/s0040-4039(00)80529-8

文献信息

• Catalytic, PMe3-mediated conversion of secondary nitroalkanes to ketones: a very mild Nef-type process
  作者：Jordi Burés、Jaume Vilarrasa

  DOI：10.1016/j.tetlet.2007.11.110

  日期：2008.1

  Aliphatic secondary nitro compounds are converted to ketones at room temperature, usually in 90–100% yields, by a one-pot reaction with 220–250 mol % of trimethylphosphine (PMe3) and 50–100 mol % of tBuC6H4SSC6H4tBu or PhthN-SePh, or 20 mol % of both additives. Thus, very mild catalytic variants of the reductive Nef-like reactions are disclosed.

  脂肪族仲硝基化合物在室温下通过一锅反应与220–250 mol％的三甲基膦（PMe 3）和50–100 mol％的t BuC 6 H 4转化为酮，通常产率为90-100％。SSC 6 H 4 t Bu或PhthN-SePh，或两种添加剂的20摩尔％。因此，公开了还原性Nef样反应的非常温和的催化变体。
• AuBr₃-Catalyzed Thiooxime-to-Carbonyl Conversion: From Chiral Aliphatic Nitro Compounds to Ketones without Racemization
  作者：Jordi Burés、Carles Isart、Jaume Vilarrasa

  DOI：10.1021/ol9017722

  日期：2009.10.1

  quantitatively in situ, in THF−H2O at pH 7, by addition of AuBr3 (but not with other MXn!). Adducts arising from asymmetric nitro-Michael and nitro-aldol reactions afford 1,4-diketones and α-alkoxy ketones, respectively, with full retention of the configuration of the stereocenters α to the CHNO2/C═N−SPh/C═O groups.

  发现了在室温下在中性条件下发生的NO 2 -CO转化（Nef反应）的新变体。在将仲硝基烷烃转化为苯硫基酮亚胺之后，这些硫肟在pH-7的THF-H 2 O中通过添加AuBr 3进行原位定量水解（但不与其他MX n！一起水解）。由不对称的硝基-迈克尔和硝基-羟醛反应产生的加合物分别提供1,4-二酮和α-烷氧基酮，并完全保留了CHNO 2 /C═N-SPh/C═O的立体中心α的构型组。
• Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines
  作者：Erik F. J. de Vries、Pablo Steenwinkel、Johannes Brussee、Chris G. Kruse、Arne van der Gen

  DOI：10.1021/jo00068a029

  日期：1993.7

  Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48. The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure. Yields were strongly affected by the size of the substituents alpha to the nitrogen atom. The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.
• Magnesium ion mediated stereospecific formation of N-substituted ethanolamines during reductive amination
  作者：Johannes Brussee、Rolf A.T.M. van Benthem、C.G. Kruse、Arne van der Gen

  DOI：10.1016/s0957-4166(00)82370-8

  日期：1990.1
• BRUSSEE, JOHANNES;BENTHEM, ROLF A. T. M. VAN;KRUSE, C. G.;GEN, ARNE VAN D+, TETRAHEDRON: ASYMMETRY, 1,(1990) N, C. 163-166
  作者：BRUSSEE, JOHANNES、BENTHEM, ROLF A. T. M. VAN、KRUSE, C. G.、GEN, ARNE VAN D+

  DOI：——

  日期：——