syn-2-methyl-3-(N-tosylamino)-3-phenyl-1-propanol

• 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: syn-2-methyl-3-(N-tosylamino)-3-phenyl-1-propanol
• 英文别名: N-((1S*,2S*)-3-hydroxy-2-methyl-1-phenylpropyl)-4-methylbenzenesulfonamide；N-[(1R,2R)-3-hydroxy-2-methyl-1-phenylpropyl]-4-methylbenzenesulfonamide
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: NXQKJNHTFQNDOU-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  syn-2-methyl-3-(N-tosylamino)-3-phenyl-1-propanol 在 ruthenium trichloride 、 sodium periodate 作用下， 生成 (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid
  参考文献：
  名称：

  Aziridine 2-carboxylate ester mediated asymmetric synthesis of α-alkyl β-amino acids

  摘要：

  The highly stereoselective ring opening of N-tosylaziridine 2-carboxylate esters with LiAlH4 followed by oxidation of the ensuing syn alcohols results in a highly efficient 4 step asymmetric synthesis of alpha-methyl beta-amino acids from N-sulfinylaziridine 2-carboxylate esters. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01095-2
• 作为产物：
  描述：

  (2-methyl-3-phenyl-1-tosylaziridin-2-yl)methanol 在 苯硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以82%的产率得到syn-2-methyl-3-(N-tosylamino)-3-phenyl-1-propanol
  参考文献：
  名称：

  羟基定向叠氮和氮丙啶氢化硅烷化反应合成1,3-氨基醇

  摘要：

  我们描述了一种由N-甲苯磺酰基1,3-氨基醇组成的方法，该方法由非环状烯丙基醇的非对映选择性叠氮化反应和前所未有的α-羟基氮丙啶区域选择性氢化硅烷化组成。该产品最多包含三个连续的立体中心。计算研究概述了叠氮化机制的关键方面，该方面与预期的不同且更加复杂。

  DOI：

  10.1002/anie.201808034

文献信息

• Studies of regio- and stereoselectivity in some nucleophilic ring opening reactions of N-tosyl-3-phenyl-2-aziridinemethanols and derivatives
  作者：David Tanner、Odd R. Gautun

  DOI：10.1016/0040-4020(95)00429-c

  日期：1995.7

  A study has been made of the regio-and Stereoselectivity of the ring opening reactions of the 3-aryl substituted aziridines 1 and 2. The regiochemical outcome is apparently decided by a balance of electronic activation at C-3 by the phenyl group and the chelating effects of C-1 oxygen functionality which can direct nucleophiles intramoleculary to C-2 or C-3. Good levels of regiocontrol for either C-3

  已经对3-芳基取代的氮丙啶1和2的开环反应的区域选择性和立体选择性进行了研究。区域化学结果显然取决于苯基和螯合在C-3上的电子活化平衡。 C-1氧官能团的作用，可以将亲核分子分子内引导至C-2或C-3。对于C-3或C-2攻击，获得了良好的区域控制水平，特别是叠氮基丁醇1a和2a与氢化物试剂反应，而甲基转移试剂，如LiMe 2 Cu和AlMe 3往往会产生独有的C-3攻击，包括倒位（碳酸）或倒位加保留（三烷基铝）。讨论了可能的反应机理（分子内与分子内）。
• Highly Enantioselective Aza-Baylis-Hillman Reactions Catalyzed by Chiral Thiourea Derivatives
  作者：Izzat T. Raheem、Eric N. Jacobsen

  DOI：10.1002/adsc.200505230

  日期：2005.10

  aza-Baylis–Hillman (ABH) reactions of N-p-nitrobenzenesulfonylimines with methyl acrylate catalyzed by chiral thiourea derivatives. A series of aromatic imines was found to undergo coupling with methyl acrylate with unprecedented levels of enantioselectivity (87–99% ee), albeit only in modest (25–49%) yields. A DABCO-acrylate-imine adduct was isolated as a key intermediate in the ABH reaction. We provide a mechanistic

  我们报道了N-硝基苯磺酰亚胺类与手性硫脲衍生物催化的丙烯酸甲酯的不对称氮杂-Baylis -Hillman（ABH）反应的发现。发现一系列芳族亚胺与丙烯酸甲酯偶合，对映选择性达到前所未有的水平（87-99％ee），尽管收率不高（25-49％）。分离出DABCO-丙烯酸酯-亚胺加合物作为ABH反应中的关键中间体。我们基于该中间体的身份以及动力学研究和同位素研究提供了机理分析，并针对观察到的产量限制提出了理论依据。还介绍了ABH产品的合成应用。
• Manipulation of substrate-controlled diastereoselectivities in hydroborations of acyclic allylamine derivatives
  作者：Kevin Burgess、Michael J. Ohlmeyer

  DOI：10.1021/jo00003a024

  日期：1991.2

  Racemic, and optically active, 2-methyl-3-(N-tosylamino)alkenes I were prepared and subjected to both catalyzed and uncatalyzed hydroborations. Data obtained for the catalyzed hydroborations of these allylamine derivatives are consistent with the theory of secondary orbital interactions in transition metal mediated processes presented in the preceding paper. Surprisingly, diastereoselectivities for conventional (uncatalyzed) hydroborations of the same substrates can be extremely sensitive to the borane used; anti products result when borane-tetrahydrofuran complex is reacted with substrates I (R' = Bn), while with 9-BBN (9-borabicyclo[3.3.1]nonane) these reactions are syn selective. Some of these results are contrary to expectations based upon experimental and theoretical data in the current literature for hydroboration of allylic alcohols. Methodology described in this paper facilitates syntheses of amine alcohols II with extremely high syn and anti selectivities.
• BURGESS, KEVIN;OHLMEYER, MICHAEL J., TETRAHEDRON LETT., 30,(1989) N3, C. 5857-5860
  作者：BURGESS, KEVIN、OHLMEYER, MICHAEL J.

  DOI：——

  日期：——
• BURGESS, K.;OHLMEYER, M. J., J. ORG. CHEM., 56,(1991) N, C. 1027-1036
  作者：BURGESS, K.、OHLMEYER, M. J.

  DOI：——

  日期：——