(R)-(-)-(Z)-pent-3-en-2-ol | 79646-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(-)-(Z)-pent-3-en-2-ol
• 英文别名: (R)-(-)-(Z)-3-penten-2-ol；(R)-(-)-Z-3-penten-2-ol；(R)-(Z)-3-penten-2-ol；(R,S)-Pent-3-en-2-ol；(Z,2R)-pent-3-en-2-ol
• CAS: 79646-46-1
• 化学式: C₅H₁₀O
• 分子量: 86.1338
• InChiKey: GJYMQFMQRRNLCY-CLBPYYFESA-N

物化性质

• 沸点：
  118.5±8.0 °C(Predicted)
• 密度：
  0.839±0.06 g/cm3(Predicted)

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：

  (R)-(-)-(Z)-pent-3-en-2-ol 在 platinum(IV) oxide 、 四丁基碘化铵 chromium(VI) oxide 、 sodium hydroxide 、 正丁基锂 、 硫酸 、 氢气 作用下， 生成 2-methyl-1-phenylpentan-1-one
  参考文献：
  名称：

  对映体富集的烯丙基苄醚的高度对映体和红细胞选择性 [2,3]-WITTIG 重排。一种新的正式手性合成 1-麻黄碱

  摘要：

  手性 (Z)-烯丙基苄基醚的 [2,3]-Wittig 重排提供了 94-97% 的不对称转移（对映特异性），以及 90-96% 的红细胞选择性。通过立体控制合成 l-麻黄碱的光学活性前体，说明了其合成潜力。

  DOI：

  10.1246/cl.1984.259
• 作为产物：
  描述：

  戊-3-炔-2-酮 在 Lindlar's catalyst Pinene 、 氢气 、 9-硼双环[3.3.1]壬烷 作用下， 生成 (R)-(-)-(Z)-pent-3-en-2-ol
  参考文献：
  名称：

  Palladium(II)-Catalyzed Exchange and Isomerization Reactions. 17. Exchange of Chiral Allyl Alcohols with Hydroxide, Methoxide, and Phenyl at High [Cl^-]. Stereochemistry of the Wacker Reaction

  摘要：

  At high [Cl-] (> 2.0 M), PdCl42- catalyzes the exchange of chiral allylic alcohols with hydroxy, methoxy, and phenyl to give chiral allyl-substituted olefins. With unsymmetrical olefins, isomerization occurs along with exchange. The hydroxyl exchange occurs in aqueous solution while the other exchanges are carried out in methanol solution. At low [Cl-] (0.1 M) oxidation to the corresponding beta-hydroxy-, methoxy-, and phenyl-substituted carbonyl compounds occurred. The absolute configurations of the oxidation and exchange products should be the same if the same mode of addition to the Pd(II)-pi-complex is operative. The absolute configurations of the oxidation and exchange products for the phenylation reaction were the same, while for hydroxy and methoxy they were different. This result indicates methanol and water must have different stereochemistries of addition at high and low [Cl-]. Thus, previous studies showing anti hydroxypalladation at high [Cl-] are not valid indicators of the stereochemistry at low [Cl-]. If anti addition occurs at high [Cl-], the addition must be syn at low [Cl-].

  DOI：

  10.1021/jo9906274

文献信息

• Palladium(II)-catalyzed dicarboxymethylation of chiral allylic alcohols: chirality transfer affording optically active diesters containing three contiguous chiral centers
  作者：Othman Hamed、Patrick M. Henry、Daniel P. Becker

  DOI：10.1016/j.tetlet.2010.04.105

  日期：2010.7

  This manuscript describes the extension of Stille’s palladium-catalyzed olefin dicarbonylation reaction to chiral allylic alcohols with chirality transfer to afford the corresponding chiral alcohol functionalized with bis-carbomethoxy esters, containing three contiguous chiral centers, in good to excellent diastereoselectivities (78–98%).

  该手稿描述了Stille的钯催化的烯烃二羰基化反应扩展到具有手性转移的手性烯丙基醇，从而得到相应的被双碳甲氧基酯官能化的手性醇，该手性醇包含三个连续的手性中心，具有良好的至优异的非对映选择性（78-98％） 。
• Stereoselective Synthesis of Erythronolide A via Nitrile Oxide Cycloadditions and Related Studies
  作者：Dieter Muri、Erick M. Carreira

  DOI：10.1021/jo901817b

  日期：2009.11.20

  An expeditious synthesis of erythronolide A is documented. Key steps of the approach include two magnesium-mediated nitrile oxide cycloadditions, a chelation-controlled Grignard reaction, and a Sharpless asymmetric dihydroxylation.

  记录了赤藓醇内酯A的快速合成。该方法的关键步骤包括两个镁介导的一氧化氮环加成反应，螯合控制的格氏反应和Sharpless不对称二羟基化反应。
• Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation. A route to substances of absolute enantiomeric purity?
  作者：Victor S. Martin、Scott S. Woodard、Tsutomu Katsuki、Yasuhiro Yamada、Masonari Ikeda、K. Barry Sharpless

  DOI：10.1021/ja00410a053

  日期：1981.10
• Total Synthesis of Erythronolide A by MgII-Mediated Cycloadditions of Nitrile Oxides
  作者：Dieter Muri、Nina Lohse-Fraefel、Erick M. Carreira

  DOI：10.1002/anie.200500172

  日期：2005.6.27
• Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis
  作者：Lee D. Fader、Erick M. Carreira

  DOI：10.1021/ol0490633

  日期：2004.7.1

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.