(2S*,3R*)-3-methyl-4-phenyl-2-butanol

• 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: (2S*,3R*)-3-methyl-4-phenyl-2-butanol
• 英文别名: syn-3-methyl-4-phenylbutan-2-ol；anti-3-methyl-4-phenylbutan-2-ol；(2R,3S)-3-methyl-4-phenylbutan-2-ol
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: VSIXJPFQJMODCS-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S*,3R*)-3-methyl-4-phenyl-2-butanol 在 N-甲基咪唑 、 碘 、 叔丁基锂 、 三苯基膦 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.6h， 生成 anti-(3,4-dimethyl-5-phenylpent1-yn-1-yl)trimethylsilane
  参考文献：
  名称：

  Diastereoselective Copper-Mediated Cross-Couplings between Stereodefined Secondary Alkylcoppers with Bromoalkynes

  摘要：

  A copper(I)-mediated cross-coupling of stereo defined secondary alkyllithiums with bromoalkynes provided stereodefined alkynes with high diastereoselectivity (dr up to 98:2). This cross-coupling was extended to various secondary alkyllithiums bearing a remote oxygen functionality, and the alkyne synthesis was also performed with optically enriched alkyl iodides (up to 99% ee) providing, after cross-coupling, alkynes bearing two stereocenters (dr = 93:7; up to 99% ee).

  DOI：

  10.1021/acs.orglett.8b00699
• 作为产物：
  描述：

  r-1-phenyl-cis-2,cis-3-dimethylcyclopropane 在 水 、 氰基萘 作用下， 以 乙腈 为溶剂， 以74%的产率得到(2S*,3R*)-3-methyl-4-phenyl-2-butanol
  参考文献：
  名称：

  Dinnocenzo; Todd; Simpson, Journal of the American Chemical Society, 1990, vol. 112, # 6, p. 2462 - 2464

  摘要：

  DOI：

文献信息

• N-Heterocyclic Carbene-Catalyzed Hydrosilylation of Styryl and Propargylic Alcohols with Dihydrosilanes
  作者：Qiwu Zhao、Dennis P. Curran、Max Malacria、Louis Fensterbank、Jean-Philippe Goddard、Emmanuel Lacôte

  DOI：10.1002/chem.201101822

  日期：2011.8.29

  Reducing alkenes to tears: Addition of structurally diverse N‐heterocyclic carbenes (NHCs) to silicon allows the reduction of propargylic and styryl alcohols through an organocatalyzed silylation/direct hydride transfer tandem reaction (see scheme). Catalytic turnover is enabled by the switch to and from hypervalent silicon. This provides a new synthetic application of NHC–main group element complexes

  减少烯烃的眼泪：在硅上添加结构多样的N杂环卡宾（NHC），可通过有机催化的甲硅烷基化/直接氢化物转移串联反应还原炔丙醇和苯乙烯醇（参见方案）。切换到高价硅可以实现催化转换。这为NHC-主族元素配合物提供了新的合成应用。
• Three-Electron S_N2 Reactions of Arylcyclopropane Cation Radicals. 1. Mechanism¹
  作者：J. P. Dinnocenzo、T. R. Simpson、H. Zuilhof、W. P. Todd、T. Heinrich

  DOI：10.1021/ja9631110

  日期：1997.2.1

  The mechanism of photosensitized nucleophilic substitution reactions on arylcyclopropanes was investigated. Stereochemical experiments with methanol, water, and cyanide as nucleophiles showed that the reactions occurred stereospecifically with complete inversion of configuration at the carbon atom undergoing substitution. Independent generation of the arylcyclopropane cation radicals by nanosecond

  研究了芳基环丙烷光敏亲核取代反应的机理。使用甲醇、水和氰化物作为亲核试剂的立体化学实验表明，反应发生立体定向，碳原子的构型完全反转进行取代。通过纳秒瞬态方法独立生成芳基环丙烷阳离子自由基表明，它们与亲核试剂快速反应，动力学在阳离子自由基和亲核试剂中均为一级。通过结合瞬态动力学和稳态 Stern-Volmer 淬灭实验，苯基环丙烷阳离子自由基与甲醇的反应与取代产物的形成在动力学上相关。
• Stereoselective Synthesis and Retentive Trapping of α-Chiral Secondary Alkyllithiums Leading to Stereodefined α,β-Dimethyl Carboxylic Esters
  作者：Varvara Morozova、Kohei Moriya、Peter Mayer、Paul Knochel

  DOI：10.1002/chem.201601911

  日期：2016.7.11

  leads to the corresponding secondary alkyllithiums with high retention of configuration. Subsequent quenching with various electrophiles such as Bu2S2, DMF, MeOB(OR)2, or Et2CO provides the desired products with retention of configuration. Furthermore, a transmetalation with CuBr⋅P(OEt)3 also allows retentive trapping with acid chlorides and ethylene oxide. The quenching of the resulting alkyllithiums

  在-100°C下用t BuLi处理α-手性仲烷基碘化物，可以得到相应的具有高构型保留性的仲烷基锂。随后用诸如Bu 2 S 2，DMF，MeOB（OR）2或Et 2 CO的各种亲电试剂淬灭，可提供所需的产物，并保留其构型。此外，用CuBr⋅P（OEt）3进行金属转移也可以用酰氯和环氧乙烷进行保持性捕集。用ClCO 2 Et淬灭生成的烷基锂，可立体选择性合成和反合成-2-乙基-2-甲基丙烯酸二乙酯羧酸盐（dr> 94％）。还制备了带有三个相邻立体控制中心（立体三单元）的相关酯。该方法已应用于以市场上可买到的顺式-2,3-环氧丁烷开始的dr = 97：3的总产率为26％的蚂蚁信息素（±）-紫杉醇的合成（四个步骤）。
• Chirality and Fragrance Chemistry:  Stereoisomers of the Commercial Chiral Odorants Muguesia and Pamplefleur
  作者：Agnese Abate、Elisabetta Brenna、Claudio Fuganti、Francesco G. Gatti、Tommaso Giovenzana、Luciana Malpezzi、Stefano Serra

  DOI：10.1021/jo048445j

  日期：2005.2.1

  The work describes the enzyme-mediated preparation and the odor evaluation of the single stereoisomers of the commercial odorants Muguesia and Pamplefleur. The synthetic approach to Muguesia stereoisomers helped to clear the assignment of the relative configuration of intermediate diols 5. The odor response of Pamplefleur isomers was found to be rather unusual. No stereoisomer prevailed, but each one

  这项工作描述了商业气味剂Muguesia和Pamplefleur的单一立体异构体的酶介导的制备和气味评估。Muguesia立体异构体的合成方法有助于清除中间二醇5的相对构型的分配。发现潘普洛夫尔异构体的气味响应是非常不寻常的。没有立体异构体占主导地位，但每个异构体在确定最终混合物的气味感方面起着确定的作用。
• Stereoselective Iridium-N,P-Catalyzed Double Hydrogenation of Conjugated Enones to Saturated Alcohols
  作者：Bram B. C. Peters、Jia Zheng、Suppachai Krajangsri、Pher G. Andersson

  DOI：10.1021/jacs.2c02422

  日期：2022.5.18

  multitude of catalytic systems have been developed for this purpose. However, due to the different nature of the π-system, the hydrogenation of olefins and ketones is normally catalyzed by different metal complexes. Herein, a study on the effect of additives on the Ir-N,P-catalyzed hydrogenation of enones is described. The combination of benzamide and the development of a reactive catalyst unlocked a

  前手性底物（如酮和烯烃）的不对称氢化是构建立体中心的重要工具，并且为此目的开发了多种催化体系。然而，由于π体系的性质不同，烯烃和酮的加氢反应通常由不同的金属配合物催化。本文介绍了添加剂对 Ir-N,P 催化的烯酮加氢影响的研究。苯甲酰胺的结合和活性催化剂的开发开启了 Crabtree 型配合物对 C=O 键加氢的新型反应模式。建议苯甲酰胺的作用是延长二氢化铱中间体的寿命，该中间体易于发生不可逆的三聚化，使催化剂失活。ee , 99/1 dr) 导致烯酮的高度立体选择性还原。