(S)-(+)-3-phenyl-3-buten-2-ol | 129646-78-2

• 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)-(+)-3-phenyl-3-buten-2-ol
• 英文别名: 3-phenylbut-3-en-2-ol；(S)-3-phenylbut-3-en-2-ol；(2S)-3-phenylbut-3-en-2-ol
• CAS: 129646-78-2
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: BCHFPTSXLVGIFV-VIFPVBQESA-N

物化性质

• 沸点：
  247.2±9.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  [2S]-3-[(S)-2-(p-tolylsulfinyl)phenyl]but-3-en-2-ol 在 叔丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 0.33h， 以72%的产率得到(S)-(+)-3-phenyl-3-buten-2-ol
  参考文献：
  名称：

  亚砜基介导的远程立体控制：通过化学选择性和非对映选择性还原γ-亚甲基δ-酮亚砜合成烯丙醇

  摘要：

  在NaBH 4溶液中进行的反应中，已证明亚磺酰基作为远程控制α，β-不饱和α-[2-（对甲苯基亚磺酰基）苯基]取代的酮1的化学选择性和非对映选择性的效率。Yb（OTf）3作为螯合剂的存在。起始的不饱和酮是由相应的2-（对甲苯磺酰基）苄基烷基（和芳基）酮2制备的通过在修饰的曼尼希条件下插入亚甲基基团，利用超声波辐照获得氨甲基化加合物，并进行硅胶处理以完全消除。还原产物的脱亚磺酰化得到具有高对映体纯度的相应的乙烯基甲醇。

  DOI：

  10.1021/jo802378s

文献信息

• Chemoenzymatic Dynamic Kinetic Resolution of Allylic Alcohols:  A Highly Enantioselective Route to Acyloin Acetates
  作者：Krisztián Bogár、Pilar Hoyos Vidal、Andrés R. Alcántara León、Jan-E. Bäckvall

  DOI：10.1021/ol071395v

  日期：2007.8.1

  Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to give the corresponding acylated acyloins in high yields without loss of chiral information.

  用南极假丝酵母脂肪酶B（CALB）和钌催化剂1进行了一系列位阻烯丙基醇的动态动力学拆分（DKR）。将得到的光学纯净的烯丙基乙酸酯进行氧化裂解，以高产率得到相应的酰化酰化酰胆碱。不会丢失手性信息。
• Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ
  作者：Shan-Shan Jiang、Bo-Qi Gu、Ming-Yu Zhu、Xingxin Yu、Wei-Ping Deng

  DOI：10.1016/j.tet.2015.01.018

  日期：2015.2

  Chiral alpha-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic alpha-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer catalyst Np-PIQ and propionic anhydride, providing moderate to good selectivity factors (S=12-37). (C) 2015 Elsevier Ltd. All rights reserved.
• Kinetic resolutions of chiral unsaturated alcohols that cannot be resolved efficiently via enantioselective epoxidation
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00176a076

  日期：1990.9
• Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00016a032

  日期：1991.7

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.