(1S*,2R*,3R*)-2,4-Dimethyl-1-phenylpentan-1,3-diol | 116047-23-5

• 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: (1S*,2R*,3R*)-2,4-Dimethyl-1-phenylpentan-1,3-diol
• 英文别名: (1SR,2RS,3RS)-1-phenyl-2,4-dimethylpentane-1,3-diol；rac-(1R,2R,3S)-1-isopropyl-2-methyl-3-phenylpropane-1,3-diol；(1S,2R,3R)-2,4-dimethyl-1-phenylpentane-1,3-diol
• CAS: 116047-23-5；116126-89-7；116126-91-1；116126-92-2
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: JEXZPZDZEAHDKZ-RTXFEEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (1S*,2R*,3R*)-2,4-Dimethyl-1-phenylpentan-1,3-diol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 生成 rac-(4R,5R,6S)-4-isopropyl-2,2,5-trimethyl-6-phenyl-[1.3]dioxane
  参考文献：
  名称：

  Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads

  摘要：

  Asymmetric aldol-Tishchenko, reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBU)(2)/Cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.

  DOI：

  10.1021/jo9003635
• 作为产物：
  描述：

  rac-(1R,2S,3S)-1-isopropyl-3-hydroxy-2-methyl-3-phenylpropyl isopropylcarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (1S*,2R*,3R*)-2,4-Dimethyl-1-phenylpentan-1,3-diol
  参考文献：
  名称：

  Tandem Aldol−Tishchenko Reactions of Lithium Enolates:  A Highly Stereoselective Method for Diol and Triol Synthesis

  摘要：

  DOI：

  10.1021/jo971012e

文献信息

• 1,2-anti diastereoselective reduction of 2-alkyl-3-hydroxy-ketones via their silyl ethers
  作者：R. Bloch、L. Gilbert、C. Girard

  DOI：10.1016/0040-4039(88)85324-3

  日期：1988.1

  T-butyldimethylsilyl ethers of a range of acyclic 2-alkyl-3-hydroxy-ketones are reduced with lithium aluminum hydride to give with a high 1,2-anti diastereoselective induction syn,anti or anti,anti 2-alkyl-1,3-diols.

  用氢化铝锂还原一系列无环2-烷基-3-羟基酮的叔丁基二甲基甲硅烷基醚，得到具有高1,2-抗非对映选择性诱导的顺，反或反2-烷基-1,3 -二醇。
• BCl₃- and TiCl₄-Mediated Reductions of β-Hydroxy Ketones
  作者：Christopher R. Sarko、Scott E. Collibee、Allison L. Knorr、Marcello DiMare

  DOI：10.1021/jo951549x

  日期：1996.1.1

  Syn-selective reduction protocols for beta-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively, Reductions are conducted at -78 degrees C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents, Added acid-scavenging agents are detrimental to reaction selectivity, An A((1,3))-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.
• The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols
  作者：Giuseppe Bartoli、Maria C. Bellucci、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Letizia Sambri

  DOI：10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x

  日期：2000.7.17

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.
• Simple Metal Alkoxides as Effective Catalysts for the Hetero-Aldol−Tishchenko Reaction
  作者：Cheryl M. Mascarenhas、Matthew O. Duffey、Shih-Yuan Liu、James P. Morken

  DOI：10.1021/ol990246c

  日期：1999.11.1

  [GRAPHICS]This paper reports the utility of simple metal alkoxides for the catalytic, stereoselective hetero-aldol-Tishchenko reaction (eq 1), Choice of metal alkoxide is crucial to achieving high efficiency and stereoselectivity, Whereas NaO-t-Bu is an effective catalyst, delivering one product in 68% yield and 99:1 stereoselection, Sm(O-i-Pr)(3) is less effective and delivers the same product in 42% yield with 4:1 stereoselection.