(S)-3-penten-2-ol | 95782-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-penten-2-ol
• 英文别名: 3-penten-2-ol；(2S)-pent-3-en-2-ol
• CAS: 95782-14-2
• 化学式: C₅H₁₀O
• 分子量: 86.1338
• InChiKey: GJYMQFMQRRNLCY-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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)-3-penten-2-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 54.08h， 生成 [tert-butyl(dimethyl)silyl] (E,3R)-3-methyl-2-[(E,2R)-pent-3-en-2-yl]hex-4-enoate
  参考文献：
  名称：

  Iterative enolate Claisen rearrangements: versatile route to optically pure 2,7-nonadiene-5-carboxylic acids

  摘要：

  A short, versatile, and diastereoselective method of preparing 2,7-nonadiene-5-carboxylic acids by an iterative enolate Claisen rearrangement procedure has been developed. Homochiral (E)- and (Z) secondary allylic alcohols 1-4, prepared from (S)-(-)-ethyl lactate, were esterified with acetic acid and enolized, and the resulting silyl ketene acetals were warmed to room temperature to effect [3,3]-sigmatropic rearrangement to 4-hexenoic acids 5-8. Esterification of these acids with alcohols 1-4 followed by a second enolate Claisen rearrangement delivered the targeted 2,7-nonadiene-5-carboxylic acids with high diastereoselectivity. This second [3,3]-sigmatropic rearrangement provides well-placed and potentially synthetically useful functionality and stereochemistry.

  DOI：

  10.1021/jo00069a019
• 作为产物：
  描述：

  3-戊炔-2-醇 在 Lindlar's catalyst 喹啉 、 whole lyophilised cells of Rhodococcus ruber DSM 、 氢气 、 丙酮 作用下， 以 phosphate buffer 、 乙醇 为溶剂， 反应 110.0h， 生成 (S)-3-penten-2-ol
  参考文献：
  名称：

  Biocatalytic oxidative kinetic resolution of sec-alcohols: stereocontrol through substrate-modification

  摘要：

  Whole lyophilised cells of Rhodococcus ruber DSM 44541 were employed for the oxidative kinetic resolution of sec-alcohols using acetone as hydrogen acceptor. The enantioselectivity of this process could be controlled effectively by introducing C-C multiple bonds into substrates, which were inefficiently recognised, in particular short-chain (omega-1)-alcohols and (omega-2)-analogs. Thus, the enantioselectivities of rac-2-pentanol (E= 16.8) and rac-3-octanol (E= 13.3) were significantly improved by introducing a C=C bond adjacent to the alcohol moiety to give racemic (E)-pent-3-en-2-ol and 4-(E)-octen-3-ol, which were resolved with excellent selectivities (E >100 and 50, respectively). In addition, it was found that high stereodifferentiation between the E- and Z-configured double bonds occurred, as the corresponding (Z)-isomers were not converted. Similar selectivity-enhancing effects were observed with acetylenic analogs. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00795-4

文献信息

• Total Synthesis of the <i>Schisandraceae</i> Nortriterpenoid Rubriflordilactone A
  作者：Guilhem Chaubet、Shermin S. Goh、Mujahid Mohammad、Birgit Gockel、Marie-Caroline A. Cordonnier、Hannah Baars、Andrew W. Phillips、Edward A. Anderson

  DOI：10.1002/chem.201703229

  日期：2017.10.9

  Full details of the total synthesis of the Schisandraceae nortriterpenoid natural product rubriflordilactone A are reported. Palladium- and cobalt-catalyzed polycyclizations were employed as key strategies to construct the central pentasubstituted arene from bromoendiyne and triyne precursors. This required the independent assembly of two AB ring aldehydes for combination with a common diyne component

  报道了五味子科降三萜类天然产物 rubriflordilactone A 的全合成细节。钯和钴催化的多环化被用作从溴戊二炔和三炔前体构建中心五取代芳烃的关键策略。这需要独立组装两个AB环醛以与共同的二炔组分结合。人们探索了许多模型系统来研究这两种方法，并建立了具有挑战性的苯并吡喃和丁烯内酯环的安装路线。
• Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities
  作者：Philipp Barbie、Uli Kazmaier

  DOI：10.1039/c6ob00800c

  日期：——

  Cyclomarins are cyclic heptapeptides containing four unusual amino acids. New synthetic protocols toward their synthesis have been developed, leading to the synthesis and biological evaluation of three natural occurring cyclomarins. Interestingly, cyclomarins address two completely different targets: Clp C1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Ase

  环豆素是含有四个不同氨基酸的环状七肽。已经开发出用于其合成的新的合成方案，从而导致了三种天然存在的环烷的合成和生物学评估。有趣的是，水手素针对两个完全不同的靶标：Clp C1，结核分枝杆菌（MTB）的酪蛋白水解蛋白酶的亚基，以及恶性疟原虫的PfAp 3 Ase 。因此，对于开发抗结核和疟疾药物而言，水手素是有趣的先导结构。
• Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐ <i>pseudo</i> ‐Rubriflordilactone B
  作者：Mujahid Mohammad、Venkaiah Chintalapudi、Jeffrey M. Carney、Steven J. Mansfield、Pollyanna Sanderson、Kirsten E. Christensen、Edward A. Anderson

  DOI：10.1002/anie.201908917

  日期：2019.12.9

  highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone B, and the proposed structure of (-)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium-catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed

  描述了天然产物 (-)-rubriflordilactone B 的合成高度收敛策略，以及 (-)-pseudo-rubriflordilactone B 的拟议结构。含有各自天然产物 FG 环的二炔与常见的 AB 环醛进行后期偶联，然后进行铑催化的 [2+2+2] 炔环三聚反应，形成天然产物骨架，只需进一步操作即可完成合成。这项工作解决了假红原二内酯 B 身份的不确定性，并为进一步的合成和生物学研究提供了一个强大的平台。
• Characterization of the monolignol oxidoreductase AtBBE-like protein 15 L182V for biocatalytic applications
  作者：Sabine Pils、Kordula Schnabl、Silvia Wallner、Marko Kljajic、Nina Kupresanin、Rolf Breinbauer、Michael Fuchs、Raquel Rocha、Joerg H. Schrittwieser、Wolfgang Kroutil、Bastian Daniel、Peter Macheroux

  DOI：10.1016/j.molcatb.2016.10.018

  日期：2016.11
• Enantioselective hydrolysis of 1-arylallyl acetates catalyzed by Candida antarctica lipase
  作者：Ekaterina N. Kadnikova、Vikalp A. Thakor

  DOI：10.1016/j.tetasy.2008.04.018

  日期：2008.5

  (R)-1-Arylallyl alcohols were obtained with excellent enantioselectivities via kinetic resolution of the corresponding acetates using immobilized Candida antarctica lipase. The scope and limitations of this reaction were investigated. The best results are obtained using the water/acetonitrile solvent system, and the reaction tolerates a variety of aryl and heteroaryl substituents. (C) 2008 Elsevier Ltd. All rights reserved.