(1S,2R)-(+)-2-(methylamino)-1,2-diphenylethanol | 46797-67-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2R)-(+)-2-(methylamino)-1,2-diphenylethanol
• 英文别名: (1S,2R)-2-methylamino-1,2-diphenyl-1-ethanol；(1S,2R)-2-(methylamino)-1,2-diphenylethanol；(1S,2R)-2-methylamino-1,2-diphenylethanol；(-)-ephenamine；(1S,2R)-ephenamine；D-erythro-α'-methylamino-bibenzyl-α-ol；(1S,2R)-2-(Methylamino)-1,2-diphenylethan-1-ol
• CAS: 46797-67-5
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: BLDFSDCBQJUWFG-CABCVRRESA-N

物化性质

• 沸点：
  355.5±9.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-(+)-2-(methylamino)-1,2-diphenylethanol 在 Penicillin G potassium 作用下， 生成 (1R,2S)-1,2-diphenyl-2-(N-methyl)aminoethanol
  参考文献：
  名称：

  1,2-Diphenyl-2-Aminoethanols. I. Synthesis of some erythro-1,2-Diphenyl-2-Alkylaminoethanols

  摘要：

  DOI：

  10.1021/jo50017a017
• 作为产物：
  描述：

  tert-Butyl ((1R,2S)-2-hydroxy-1,2-diphenylethyl)carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以83%的产率得到(1S,2R)-(+)-2-(methylamino)-1,2-diphenylethanol
  参考文献：
  名称：

  Enantioselective synthesis of (1S,2R)-ephenamine

  摘要：

  DOI：

  10.1016/j.tetasy.2016.02.013

文献信息

• Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols
  作者：Lacie C. Hirayama、Soya Gamsey、Daniel Knueppel、Derek Steiner、Kelly DeLaTorre、Bakthan Singaram

  DOI：10.1016/j.tetlet.2005.01.169

  日期：2005.3

  enantioselective allylation of both aromatic and aliphatic aldehydes using commercially available (1S,2R)-(+)-2-amino-1,2-diphenylethanol as a chiral auxiliary. Using only two equivalents of allyl bromide, excellent yields and very good to excellent enantioselectivities are obtained. To our knowledge, the enantioselectivities reported herein are the highest obtained for indium-promoted allylations of carbonyl

  我们报告了使用市售（1 S，2 R）-（+）-2-氨基-1,2-二苯乙醇作为手性助剂的铟介导的芳香族和脂肪族醛的Barbier型对映选择性烯丙基化的一般方法。仅使用两个当量的烯丙基溴，可获得优异的产率和非常好的至优异的对映选择性。据我们所知，本文报道的对映选择性是由铟促进的羰基化合物的烯丙基化所获得的。
• Asymmetric hydrogenation of chiral vinyloxazaborolidines under ambient conditions
  作者：Soya Gamsey、Kelly DeLaTorre、Bakthan Singaram

  DOI：10.1016/j.tetasy.2004.11.091

  日期：2005.2

  vinyloxazaborolidines have been synthesized and subsequently hydrogenated using palladium on carbon under ambient conditions to produce, after oxidation of the boronate group, enantiomerically enriched secondary alcohols (up to 20% ee). Herein, the first example of asymmetric hydrogenation utilizing oxazaborolidines as chiral auxiliaries is reported.

  已经合成了新的高手性乙烯基氧杂氮杂硼烷，随后在环境条件下使用钯/碳将其氢化，以在硼酸酯基团氧化后产生对映体富集的仲醇（至多20％ee）。在此，报道了利用恶唑硼烷作为手性助剂的不对称氢化的第一个例子。
• A Simple, Scalable Synthetic Route to (+)- and (−)-Pseudoephenamine
  作者：Kevin T. Mellem、Andrew G. Myers

  DOI：10.1021/ol402815d

  日期：2013.11

  A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivative of benzil, reduction of that substance with lithium aluminum hydride, and resolution of pseudoephenamine with mandelic acid.

  描述了一种三步合成伪苯胺，适用于从廉价的起始材料苯并制备数克数量的助剂的两种对映异构体。该序列包括合成苄基的结晶单甲基亚胺衍生物，用氢化铝锂还原该物质，以及用扁桃酸拆分伪苯胺。
• Asymmetric Synthesis XXVIII: Novel Chiral Aminophosphine Phosphinite Ligand and Its Application in Homogenous Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Derivatives
  作者：Aiqiao Mi、Rongliang Lou、Yaozhong Jiang、Jingen Deng、Yong Qin、Fangmin Fu、Zhi Li、Wenhao Hu、Albert S. C. Chan

  DOI：10.1055/s-1998-1821

  日期：1998.8

  Novel chiral aminophosphine phosphinite, DPAMPP was designed and synthesized from (1S,2R)-1,2-diphenyl-2-aminomethanol. Its cationic rhodium complex has been found to be an excellent catalyst for enantioselective hydrogenation of dehydroamino acids (more than 95.0% e.e.).

  新型手性氨基膦膦酸酯DPAMPP是由(1S,2R)-1,2-二苯基-2-氨基甲醇设计和合成的。其阳离子铑配合物被发现是一种优良的催化剂，能够对脱氨基酸进行优异的选择性氢化（对映体过量超过95.0%）。
• Towards Enantioselective Nucleophilic Trifluoromethylation
  作者：Solveig Roussel、Thierry Billard、Bernard R. Langlois、Laurent Saint-James

  DOI：10.1002/chem.200400777

  日期：2005.1.21

  Various trifluoroacetamides and trifluoromethanesulfinamides, derived from chiral silylated amino alcohols, have been synthesized with the goal of achieving enantioselective nucleophilic trifluoromethylation. The best results were obtained with (R)-phenylglycinol derivatives, but the ee values did not exceed 30 %.

  为了达到对映选择性亲核三氟甲基化的目的，已经合成了衍生自手性甲硅烷基化氨基醇的各种三氟乙酰胺和三氟甲亚磺酰胺。（R）-苯基甘氨醇衍生物获得了最佳结果，但ee值不超过30％。