(2R*,3R*)-2-methyl-3-phenyl-1,3-butanediol | 14366-96-2

• 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: (2R*,3R*)-2-methyl-3-phenyl-1,3-butanediol
• 英文别名: (2R,3R)-2-methyl-3-phenylbutane-1,3-diol
• CAS: 14366-96-2
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: BJTAASQKZZKUNV-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R*,3R*)-2-methyl-3-phenyl-1,3-butanediol 在 potassium permanganate 、 sodium carbonate 作用下， 生成 (2S^*,3R^*)-3-Hydroxy-2-methyl-3-phenylbutansaeure
  参考文献：
  名称：

  The Cleavage Reaction of 1,3-Diols. III. The Synthesis of a Pair of Diastereomeric Ditertiary 1,3-Diols and an Effect of Configuration on Mode of Cleavage¹

  摘要：

  DOI：

  10.1021/ja01638a003
• 作为产物：
  描述：

  (E)-3-phenylbut-2-en-1-ol 在 lithium dimethylcuprate 作用下， 生成 (2R*,3R*)-2-methyl-3-phenyl-1,3-butanediol
  参考文献：
  名称：

  Stereoselective addition of organoaluminium or organomanganese reagents to 2-methyl-3—oxo amides (or esters) providing erythro or threo 2-methyl-3-hydroxy amides (or esters)

  摘要：

  Treatment of 2-methyl-3-oxo amides or 2-methyl-3-oxo esters with trialkylaluminium or alkylmanganese halide provided the corresponding erythro (or threo) 3-hydroxy-2-methyl amides or 3-hydroxy-2-methyl esters with high stereoselectivity.

  DOI：

  10.1016/s0040-4039(00)74258-4

文献信息

• Reaction of 2-Hydroxy-1,2,2-triphenylethyl Propionate with Non-Activated Ketones and Enones: Stereoselective Aldol and Michael Addition
  作者：Manfred Braun、Brigitte Mai、Daniel Ridder

  DOI：10.1002/1099-0690(200108)2001:16<3155::aid-ejoc3155>3.0.co;2-8

  日期：2001.8

  reaction of the silyl ketene acetal 2, derived from (R)-propionate 1, with the ketones 3a−d occurs in a stereoselective manner. The aldol product 4c is obtained from the enone 3c, whereas the homologous compound 3d undergoes a 1,4 addition and leads to the keto ester 5. The configurations of the deprotected aldol adduct 6 (obtained from 3c) and the Michael product 5 are determined by crystal structure

  TiCl 4介导的（R）-丙酸酯1的甲硅烷基乙烯酮缩醛2与酮3a - d的Mukaiyama型反应与立体异构体发生。醛醇产物4c从烯酮3c获得，而同源化合物3d经历1，4加成并生成酮酸酯5。通过晶体结构分析确定脱保护的羟醛加合物6（从3c获得）和迈克尔产物5的构型。非对映体和对映体纯酯制备4a - c，5和6，以及包含两个或三个连续的立体碳中心的羧酸7和二醇8。对映体纯的化合物7和8是由可回收的手性辅助试剂1,1,2-三苯基-1,2-乙二醇的裂解产生的。
• 1,2 asymmetric induction in the TiCl4 mediated alkylation of α-methyl-β-silyloxy ketones with Grignard reagents
  作者：Giuseppe Bartoli、Marcella Bosco、Letizia Sambri、Enrico Marcantoni

  DOI：10.1016/s0040-4039(97)00735-1

  日期：1997.5

  Transmetallation of an α-methyl-β-silyloxy ketone with TiCl4 in toluene affords a cyclic chelation complex which undergoes highly stereoselective alkylation from Grignard reagents at the less hindered side.

  用甲苯中的TiCl 4对α-甲基-β-甲硅烷氧基酮进行金属转移，得到环状螯合配合物，该螯合配合物在较少受阻的一侧从格氏试剂进行高度立体选择性的烷基化反应。
• Substituent effects on the magnetic nonequivalence in the PMR signals of isopropyl Me protons of 2-aryl-3-methyl-2-butanols
  作者：A.P.G. Kieboom、A. Sinnema

  DOI：10.1016/0040-4020(72)80087-5

  日期：1972.1

  The influence of substituents in the aromatic nucleus of 2-aryl-3-methyl-2-butanols (1) on the magnetic nonequivalence of the isopropyl Me protons was investigated. Quantitative correlations were obtained with the aid of the Hammett-Yukawa and Taft equations. The origin of the phenomena is discussed in terms of preferred conformations of 1 and the diamagnetic anisotropy of the aromatic nucleus.

  研究了2-芳基-3-甲基-2-丁醇（1）的芳核中取代基对异丙基Me质子磁非等价性的影响。借助Hammett-Yukawa和Taft方程获得定量相关性。现象的起源是根据1的优选构型和芳香核的反磁各向异性来讨论的。
• Internal Lewis Acid Coordination as a Powerful Tool To Promote Highly Stereoselective Alkylation ofα-Alkyl-β-Hydroxy Ketones with Grignard Reagents
  作者：Giuseppe Bartoli、M. Cristina Bellucci、Marcella Bosco、Enrico Marcantoni、Letizia Sambri

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2154::aid-chem2154>3.0.co;2-o

  日期：1998.11.2

  An efficient and highly diastereoselective protocol is described for the alkylation of beta-hydroxy ketones that contain an a-stereocenter. This method is based on the preliminary transformation of the beta-hydroxy group into a titanium alcoholate by means of the facile transmetalation of the corresponding beta-silyloxy derivative with TiCl4 (Method A) or by reaction of the lithium alcoholate with TiCl4 (Method B). On account of the strong internal coordinating action of the Lewis acid, this intermediate assumes a rigid half-chair conformation with the alpha-alkyl substituent in a pseudoaxial position, This geometrical arrangement facilitates the attack of the entering carbanion on the carbonylic function apposite to the alpha-substituent. The method uses simple Grignard reagents as the alkylating agents and allows the addition of a wide variety of carbon frameworks to the carbonyl function. including primary and secondary alkyl chains, arylic, alkynylic, vinylic, and benzylic moieties, with high efficiency and stereoselectivity.
• Canceill,J. et al., Bulletin de la Societe Chimique de France, 1966, p. 2653 - 2658
  作者：Canceill,J. et al.

  DOI：——

  日期：——