(S,E)‐1‐phenylpenta‐1,4‐dien‐3‐ol | 129646-80-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (S,E)‐1‐phenylpenta‐1,4‐dien‐3‐ol
• 英文别名: (S)-(+)-(E)-1-phenylpenta-1,4-dien-3-ol；(S,E)-1-phenylpenta-1,4-dien-3-ol；(4E,3S)-5-phenylpent-1-en-3-ol；(1E,3S)-1-phenylpenta-1,4-dien-3-ol
• CAS: 129646-80-6
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: YITIUMGRXQMJTQ-FBOQAHMBSA-N

物化性质

• 沸点：
  291.3±9.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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,E)‐1‐phenylpenta‐1,4‐dien‐3‐ol 在 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 copper(l) iodide 、 calcium hydride 、 MS 3 Angstroem 、 四丁基氟化铵 、 D-(-)-酒石酸二异丙酯 作用下， 以 四氢呋喃 、 异辛烷 、 二氯甲烷 为溶剂， 反应 25.84h， 生成 (1E,3R,4S)-1-Phenylhex-1-ene-3,4-diol
  参考文献：
  名称：

  不对称二乙烯基甲醇无尖锐不对称环氧化的研究

  摘要：

  外消旋不对称二乙烯基甲醇rac -13在Sharpless不对称环氧化条件下，使用化学计量的四异丙氧基钛[Ti（OP i）4]，D -（-）-酒石酸二异丙酯（DIPT）和叔丁基氢过氧化物（TBHP）进行反应R -14和R -15的收率分别为41％和43％，ee均> 99％，其中动力学拆分和随后的环氧化反应均以完全区域选择性和非对映选择性的方式进行。

  DOI：

  10.1039/p19960001729
• 作为产物：
  描述：

  (E)-1-phenyl-1,4-pentadien-3-ol 以41%的产率得到(S,E)‐1‐phenylpenta‐1,4‐dien‐3‐ol
  参考文献：
  名称：

  Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp

  摘要：

  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.

  DOI：

  10.1021/ja00016a032

文献信息

• Enantioselective Alkenylation and Phenylation Catalyzed by a Chiral CuF Complex
  作者：Daisuke Tomita、Reiko Wada、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ja0507362

  日期：2005.3.1

  A new method for CuF-catalyzed alkenylation and phenylation of aldehydes and an activated ketone using air- and moisture-stable alkenylsilanes and phenylsilane as a nucleophile is described. This methodology was extended to highly enantioselective catalytic alkenylation and phenylation using DTBM-SEGPHOS as a chiral ligand. Substrate generality is broad, and an alkenylsilane with a long alkyl chain

  描述了一种使用空气和湿气稳定的烯基硅烷和苯基硅烷作为亲核试剂对醛和活化酮进行 CuF 催化的烯基化和苯基化的新方法。这种方法被扩展到使用 DTBM-SEGPHOS 作为手性配体的高度对映选择性催化烯基化和苯基化。底物通用性广，具有长烷基链和内部烯基硅烷的烯基硅烷也可用作亲核试剂。成功的关键部分涉及通过甲硅烷基化亲核试剂的金属转移加速反应性烯基铜和苯基铜的再生，以及反应性铜试剂的稳定化，这两者都受二膦配体的影响。
• A highly enantioselective synthesis of chiral allylic alcohols by asymmetric addition of novel mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes
  作者：Itaru Sato、Noriaki Asakura、Taizo Iwashita

  DOI：10.1016/j.tetasy.2007.10.031

  日期：2007.11

  A novel mixture of reagents of trialkenylbismuthines/dialkylzincs was developed and applied toward the synthesis of chiral allylic alcohols. The chiral β-amino alcohols catalyzed addition of the mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes gave enantiomerically enriched allylic alcohols with up to 97% ee.

  开发了一种新的三烯基双突变体/二烷基锌试剂混合物，并将其用于手性烯丙基醇的合成。手性β-氨基醇催化将三烯基双突变蛋白/二烷基锌的混合试剂加成到醛中，得到对映体富集的烯丙醇，其ee高达97％。
• Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs
  作者：Pei Wang、Guo-Rong Ma、Sheng-Li Yu、Chao-Shan Da

  DOI：10.1002/chir.23038

  日期：2019.1

  Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long‐standing challenge. This work demonstrated that the magnesium (S)‐3,3′‐dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2‐[N,N′‐dimethylamino]ethyl) ether (BDMAEE) in the addition

  醛类的直接催化不对称格氏反应和乙烯基格林纳德试剂对醛的对映选择性乙烯基化是一个长期的挑战。这项工作表明，（S）-3,3'-二甲基双酚镁对映体选择性地通过双（2- [ N，N'-二甲基氨基]乙基）醚（BDMAEE）与失活的乙烯基溴化镁对醛进行直接乙烯基化。添加正丁基氯化镁。迄今为止，达到了63％的最高ee。
• 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
• 2,6-Bis(2-alkylphenyl)-3,5-dimethylphenol as a New Chiral Phenol with <i>C</i>₂-Symmetry. Application to the Asymmetric Alkylation of Aldehydes
  作者：Susumu Saito、Taichi Kano、Keiko Hatanaka、Hisashi Yamamoto

  DOI：10.1021/jo970747g

  日期：1997.8.1