(1R,2S)-(-)-2-(methylamino)-1-phenyl-1<(tert-butyldimethylsilyl)oxy>-propane | 130647-17-5

• 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: (1R,2S)-(-)-2-(methylamino)-1-phenyl-1<(tert-butyldimethylsilyl)oxy>-propane
• 英文别名: (1R,2S)-(-)-2-(methylamino)-1-phenyl-1-<(t-butyldimethylsilyl)oxy>-propane；(1R,2S)-(-)-2-(methylamino)-1-phenyl-1-[(t-butyldimethylsilyl)oxy]propane；(1R,2S)-(-)-2-(Methylamino)-1-phenyl-1-[(tert-butyldimethyl-silyl)oxy]-propane；(1R,2S)-(-)-2-(Methylamino)-1-phenyl-1-[(tert.butyldimethyl-silyl)oxy]-propane；(1R,2S)-(-)-2-(methylamino)-1-phenyl-1-[(t-butyldimethylsilyl)oxy]-propane；(1R,2S)-1-{[tert-Butyl(dimethyl)silyl]oxy}-N-methyl-1-phenylpropan-2-amine；(1R,2S)-1-[tert-butyl(dimethyl)silyl]oxy-N-methyl-1-phenylpropan-2-amine
• CAS: 130647-17-5
• 化学式: C₁₆H₂₉NOSi
• 分子量: 279.498
• InChiKey: WIKYZIWJVSQTNP-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-(-)-2-(methylamino)-1-phenyl-1<(tert-butyldimethylsilyl)oxy>-propane 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2S)-(+)-(N-diphenylphosphinyl)ephedrine
  参考文献：
  名称：

  开发用于合成高度旋光的α，γ-取代的γ-丁内酯的新反应系统。

  摘要：

  已经开发了用于合成旋光的α，γ-取代的γ-丁内酯的非常有用的方法。SmI（2）诱导的异山梨醇与酮的手性2-烷基丙烯酸2-烷基酯的还原偶联，在存在（1S）-（-）-2,10-樟脑作为质子源的情况下，得到手性α，γ取代的γ -丁内酯，收率高，对映体纯度高（反式可高达99％ee，顺式可高达75％ee）。已经用各种酮研究了该反应系统，并且证明该系统对于反式α，γ-取代的γ-丁内酯是非常有效的。为了观察到优异的产品ee值，该系统中的手性助剂和受阻质子源都是必需的。

  DOI：

  10.1021/jo0155153
• 作为产物：
  描述：

  (R)-(+)-α-<(tert-butyldimethylsilyl)oxy>-benzeneacetonitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.5h， 生成 (1R,2S)-(-)-2-(methylamino)-1-phenyl-1<(tert-butyldimethylsilyl)oxy>-propane
  参考文献：
  名称：

  Brussee, J.; Gen, A. van der, Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 1, p. 25 - 26

  摘要：

  DOI：

文献信息

• Asymmetric Induction during Yang Cyclization of α-Oxoamides:  The Power of a Covalently Linked Chiral Auxiliary Is Enhanced in the Crystalline State
  作者：Arunkumar Natarajan、Joel T. Mague、V. Ramamurthy

  DOI：10.1021/ja043999p

  日期：2005.3.1

  Gamma-hydrogen abstraction has been revealed to be the primary photoprocess in the crystalline state of alpha-oxoamides through photochemical and X-ray structural studies. The outstanding ability of a covalent chiral auxiliary in generating asymmetric induction in the photoproduct beta-lactam has been established with 10 examples. We have shown that the crystal lattice preorganizes the reactant molecules

  通过光化学和 X 射线结构研究，γ-氢提取已被揭示是 α-氧代酰胺结晶状态的主要光处理过程。共价手性助剂在光产物 β-内酰胺中产生不对称诱导的杰出能力已通过 10 个例子得到证实。我们已经表明，晶格将反应物分子预组织为 β-内酰胺的单个非对映异构体，并防止 1,4-双基中间体的大运动，这将导致立体化学记忆的丧失。所研究的一个实例的罕见单晶到单晶转化路径建立了反应物和产物的立体化学之间的直接相关性。
• Enhanced Diastereoselectivity via Confinement:  Photoisomerization of 2,3-Diphenylcyclopropane-1-carboxylic Acid Derivatives within Zeolites
  作者：J. Sivaguru、Raghavan. B. Sunoj、Takehiko Wada、Yumi Origane、Yoshihisa Inoue、Vaidhyanathan Ramamurthy

  DOI：10.1021/jo049365i

  日期：2004.10.1

  From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding-dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.
• Synthesis and preliminary studies on a novel class of soluble amino alcohol reagents based on methacrylate copolymers
  作者：Christopher W Edwards、David M Haddleton、David Morsley、Mark R Shipton、Martin Wills

  DOI：10.1016/s0040-4020(03)00975-x

  日期：2003.7

  A class of soluble polymers containing chiral beta-amino alcohol ligands, based on methacryate copolymers, are described. The use of copolymers permits the selective introduction of material to control the solubility and a functional group in a controllable ratio and polymer length. The application of the supported polymers to diethylzinc additions is described. (C) 2003 Elsevier Ltd. All rights reserved.
• 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, J.;VAN, DER GEN A., REC. TRAV. CHIM. PAYS-BAS, 110,(1991) N, C. 25-26
  作者：BRUSSEE, J.、VAN, DER GEN A.

  DOI：——

  日期：——