(S)-1-phenylpent-4-en-2-ol | 122332-14-3

• 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: (S)-1-phenylpent-4-en-2-ol
• 英文别名: (I+/-S)-I+/--2-Propen-1-ylbenzeneethanol；(2S)-1-phenylpent-4-en-2-ol
• CAS: 122332-14-3
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: YQNUFNXWLWCHSH-NSHDSACASA-N

物化性质

• 沸点：
  266.5±9.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (S)-1-phenylpent-4-en-2-ol 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  6-Deoxyerythronolide B Synthase Thioesterase-Catalyzed Macrocyclization Is Highly Stereoselective

  摘要：

  Macrocyclic polyketide natural products are an indispensable source of therapeutic agents. The final stage of their biosynthesis, macrocyclization, Is catalyzed regio- and stereoselectively by a thioesterase. A panel of substrates were synthesized to test their specificity for macrocyclization by the erythromycin polyketide synthase TE (DEBS TE) in vitro. It was shown that DEBS TE is highly stereospecific, successfully macrocyclizing a 14-member ring substrate with an R configured O-nucleophile, and highly regioselective, generating exclusively the 14-member lactone over the 12-member lactone.

  DOI：

  10.1021/ol300707j
• 作为产物：
  描述：

  1-phenylpent-4-en-2-ol 在 乙酸乙烯酯 、 Novozym 435 作用下， 以 异丙醚 为溶剂， 反应 40.0h， 以36%的产率得到(S)-1-phenylpent-4-en-2-ol
  参考文献：
  名称：

  Chemoenzymatic asymmetric synthesis of harzia lactone A stereomers

  摘要：

  A facile chemoenzymatic synthesis of the harzia lactone A enantiomers was developed. A lipase-catalyzed acylation and an enantio-controlled substrate and reagent-con trol led Sharpless' asymmetric dihydroxylation are the key features of the synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.009

文献信息

• Oxazoline derivatives tagged with tosylated amino acids as recyclable organocatalysts for enantioselective allylation of aldehydes
  作者：Debashis Ghosh、Arghya Sadhukhan、Nabin Ch. Maity、Sayed H. R. Abdi、Noor-ul H. Khan、Rukhsana I. Kureshy、Hari C. Bajaj

  DOI：10.1039/c3ra47424k

  日期：——

  of amino acid-based oxazoline compounds have been prepared and successfully applied to the enantioselective allylation reaction of aldehydes. The fine-tuning of the structure of the oxazolines led to (S,S)-4 as an efficient organocatalyst which gave homoallyl alcohols in good yield (up to 90%) and excellent ee (up to 99%) for a wide range of substrates including aromatic, hetero-aromatic and α,β-unsaturated

  已经制备了一系列基于氨基酸的恶唑啉化合物并将其成功地用于醛的对映选择性烯丙基化反应。恶唑啉结构的微调导致了（S，S）-4作为一种有效的有机催化剂，在很宽的范围内都能得到高收率（高达90％）和良好的ee（高达99％）的均烯丙基醇。底物包括芳族，杂芳族和α，β-不饱和醛。通过三个简单的步骤合成了手性有机催化剂，总收率达88％，并成功地回收了多达三个循环。根据实验观察结果和NMR研究，提出了该反应的可能机理。
• Dynamic Kinetic Resolution of Homoallylic Alcohols: Application to the Synthesis of Enantiomerically Pure 5,6-Dihydropyran-2-ones and δ-Lactones
  作者：Madeleine C. Warner、Grigory A. Shevchenko、Suzan Jouda、Krisztián Bogár、Jan-E. Bäckvall

  DOI：10.1002/chem.201301980

  日期：2013.10.4

  Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transformed into homoallylic acrylates after hydrolysis of the ester function and subsequent DMAP‐catalyzed esterification with acryloyl chloride. After ring‐closing

  使用南极假丝酵母脂肪酶B和钌催化剂2对各种均烯丙基醇进行动态动力学拆分，可得到高收率和高对映选择性的均烯丙基乙酸酯。酯官能团水解后，这些对映体纯乙酸酯进一步转化为均烯丙基丙烯酸酯，随后通过DMAP催化用丙烯酰氯酯化。开环易位后，获得了5,6-二氢吡喃-2-酮。碳碳双键的选择性加氢可提供相应的δ-内酯，而不会丢失手性信息。
• Enantioselective 1,2-Anionotropic Rearrangement of Acylsilane through a Bisguanidinium Silicate Ion Pair
  作者：Weidi Cao、Davin Tan、Richmond Lee、Choon-Hong Tan

  DOI：10.1021/jacs.7b13056

  日期：2018.2.7

  bisguanidinium-catalyzed tandem rearrangements of acylsilanes are reported. The acylsilanes were activated via an addition of fluoride on the silicon to form a penta-coordinate anionic silicate intermediate. The silicate then underwent alkyl or aryl group migration from the silicon atom to the neighboring carbonyl carbon atom (1,2-anionotropic rearrangement), followed by [1,2]-Brook rearrangement to provide the secondary

  报道了高度对映选择性双胍催化的酰基硅烷串联重排。通过在硅上添加氟化物来活化酰基硅烷以形成五配位阴离子硅酸盐中间体。然后硅酸盐经历烷基或芳基从硅原子迁移到相邻的羰基碳原子（1,2-阴离子重排），然后进行 [1,2]-布鲁克重排，以高产率提供具有优异对映选择性的仲醇（高达 95% ee）。α-甲硅烷基甲醇中间体的分离以及 DFT 计算表明，1,2-阴离子重排是通过双胍硅酸盐离子对发生的，这是立体确定步骤。然后通过随后的 [1,2]-布鲁克重排保留形成的手性中心而不发生反转。巴豆酰基硅烷顺利转化为高烯丙基线性巴豆醇，保留 E/Z 几何结构，未检测到支链醇。这清楚地表明 1,2-阴离子重排是通过三元而不是五元过渡态发生的。
• Towards a characterization of the structural determinants of specificity in the macrocyclizing thioesterase for deoxyerythronolide B biosynthesis
  作者：Panos Argyropoulos、Fabien Bergeret、Christophe Pardin、Janice M. Reimer、Atahualpa Pinto、Christopher N. Boddy、T. Martin Schmeing

  DOI：10.1016/j.bbagen.2015.11.007

  日期：2016.3

  Type I polyketide synthases (PKSs) are giant multidomain proteins that synthesize many therapeutics and other natural products. The synthesis proceeds by a thiotemplate mechanism whereby intermediates are covalently attached to the PKS. The release of the final polyketide is catalyzed by the terminal thioesterase (TE) domain through hydrolysis, transesterification, or macrocyclization. The PKS 6-deoxyerythronolide

  I型聚酮化合物合酶（PKS）是巨大的多域蛋白，可合成许多治疗剂和其他天然产物。合成通过硫代模板机理进行，其中中间体共价附于PKS。最终的聚酮化合物的释放是通过末端硫酯酶（TE）域通过水解，酯交换或大环化来催化的。PKS 6-脱氧赤藓醇B合酶（DEBS）产生具有临床意义的抗生素红霉素的14元大环内酯核心。DEBS的TE结构域（DEBS TE）对天然和修饰底物的水解或大环化具有公认的，经验确定的特异性。我们目前正在努力了解使用一组新颖的二苯基烷基膦酸酯在DEBS TE中硫酯酶反应特异性的结构基础，模拟由DEBS TE专门环化或水解的底物。我们已经确定了仅在1.7Å处的DEBS TE的新构建体的结构，并且以2.1Å的分辨率与简单的烯丙基膦酸酯结合的DEBS TE。其他更复杂的二苯基烷基膦酸酯会抑制DEBS TE，但我们无法可视化这些与DEBS TE配合的忠实环化类似物。这项工作代表着使用与复杂底物类似物复合的DEBS
• Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters
  作者：Chenlong Zhang、Weipeng Hu、Gabriel J. Lovinger、Jing Jin、Jingjia Chen、James P. Morken

  DOI：10.1021/jacs.1c05274

  日期：2021.9.8

  In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate

  本文描述了通过乙烯基硼酸酯的催化对映选择性碳氧化合成对映体富集、构型稳定的有机锌试剂。该工艺提供了富含对映体的 α-硼锌中间体，这些中间体经证明会发生立体定向反应，从而产生富含对映体的仲硼酸酯产品。探索了中间体α-硼锌试剂的性质，并通过将其应用于(-)-aphanorphine和(-)-enterolactone的合成证明了产物的合成效用。