(S)-(+)-1-phenyl-4-penten-1-yn-3-ol | 129646-82-8

• 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-phenyl-4-penten-1-yn-3-ol
• 英文别名: 5-phenylpent-1-en-4-yn-3-ol；(3S)-5-phenylpent-1-en-4-yn-3-ol
• CAS: 129646-82-8
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: WRCNAZRAXFXPTH-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-苯基-4-戊烯-1-炔-3-醇 以43%的产率得到(S)-(+)-1-phenyl-4-penten-1-yn-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

• Chiral Macrocycle-Catalyzed Highly Enantioselective Phenylacetylene Addition to Aliphatic and Vinyl Aldehydes
  作者：Zi-Bo Li、Tian-Dong Liu、Lin Pu

  DOI：10.1021/jo070091j

  日期：2007.6.1

  The 1,1‘-binaphthyl macrocycle (S)-2 is found to be an excellent catalyst for the alkyne addition to aldehydes. In the presence of (S)-2 (20 mol %) and Me2Zn (2 equiv) in THF at room temperature, the addition of phenylacetylene to linear or branched aliphatic aldehydes and vinyl aldehydes gave various propargylic alcohols with 89−96% ee.

  发现1,1'-联萘大环（S）-2是炔烃加成醛的极佳催化剂。在室温下，在THF中存在（S）-2（20 mol％）和Me 2 Zn（2当量）的情况下，将苯乙炔添加到直链或支链脂族醛和乙烯基醛中，制得89-96％的各种炔丙醇ee。
• Zn(ODf)2: preparation and application in asymmetric alkynylation of aldehydes
  作者：Zili Chen、Wennan Xiong、Biao Jiang

  DOI：10.1039/b206868k

  日期：2002.9.11

  A new Lewis acid, Zn(ODf)2, was first prepared from commercially available 3,3,4,4-tetrafluoro[1,2]oxathietane 2,2-dioxide in four steps with 56% yields and also was applied to catalyze highly enantioselective alkynylation of aldehydes in the presence of ligand (1S,2S)-3-(tert-butyldimethylsilyloxyl)-2-N,N-dimethylamino-1-(p-nitrophenyl)propane-1-ol or ligand (−)-N-methylephedrine to afford the corresponding propargylic alcohols in high yields with up to 99% ee.

  一种新型路易斯酸Zn(ODf)2首次通过商购的3,3,4,4-四氟[1,2]氧硫杂环己烷2,2-二氧化物经四步反应以56%的产率制备得到，并被应用于催化醛的高度对映选择性炔基化反应，在配体(1S,2S)-3-(叔丁基二甲基硅氧基)-2-N,N-二甲基氨基-1-(对硝基苯基)丙烷-1-醇或配体(-)-N-甲基麻黄碱的存在下，以高产率得到相应的炔丙醇，对映体过量率高达99% ee。
• Iridium-Catalyzed Asymmetric Allylation of Indoles via Kinetic Resolution of 1-Alken-4-yn-3-ols
  作者：Ryo Takeuchi、Takahiro Sawano、Yuki Yasumura、Kyohei Kuwabara、Hikaru Sugiura、Kana Takahashi、Eri Ishikawa

  DOI：10.1055/a-2108-9720

  日期：2023.12

  We report the iridium-catalyzed asymmetric allylation of indoles via kinetic resolution of 1-alken-4-yn-3-ols to form chiral 1-alken-4-yn-3-ols and branched allylated products with high selectivity. 1-Alken-4,6-diyn-3-ol was also found to be suitable for this asymmetric allylation and gave the products in high yield and enantioselectivity. Other nucleophiles such as a malonic ester and a thiol, besides

  我们报道了铱催化的吲哚不对称烯丙基化，通过 1-alken-4-yn-3-ols 的动力学拆分形成手性 1-alken-4-yn-3-ols 和高选择性的支链烯丙基化产物。1-Alken-4,6-diyn-3-ol 也被发现适合这种不对称烯丙基化，并且得到高产率和对映选择性的产物。除吲哚外，其他亲核试剂如丙二酸酯和硫醇也可反应生成具有高对映选择性的烯丙基化产物和1-烯-4-yn-3-醇。
• Catalytic Asymmetric Transfer Hydrogenation of Acylboronates: BMIDA as the Privileged Directing Group
  作者：Xiangjian Meng、Shouang Lan、Ting Chen、Haotian Luo、Lixuan Zhu、Nanchu Chen、Jinggong Liu、Shuang Yang、Andrej Emanuel Cotman、Qi Zhang、Xinqiang Fang

  DOI：10.1021/jacs.4c05924

  日期：2024.7.24

  general, highly efficient, and enantioselective catalytic method for the synthesis of chiral alcohols is still a formidable challenge. We report in this article the asymmetric transfer hydrogenation (ATH) of N-methyliminodiacetyl (MIDA) acylboronates as a general substrate-independent entry to enantioenriched secondary alcohols. ATH of acyl-MIDA-boronates with (het)aryl, alkyl, alkynyl, alkenyl, and

  开发一种通用、高效、对映选择性的催化方法来合成手性醇仍然是一个艰巨的挑战。我们在本文中报道了N-甲基亚氨基二乙酰 (MIDA) 酰基硼酸酯的不对称转移氢化 (ATH) 作为一般的不依赖于底物的进入对映体富集仲醇的方法。具有（杂）芳基、烷基、炔基、烯基和羰基取代基的酰基-MIDA-硼酸酯的 ATH 可产生多种对映体富集的 α-硼醇。后者用于一系列基于硼部分的立体有择转化，能够合成具有两个密切相关的 α-取代基的甲醇，而使用直接不对称氢化方法无法获得高对映选择性，例如 ( R )-氯哌斯汀中间的。计算研究表明，与传统使用的芳基和炔基相比，BMIDA 基团是 Noyori-Ikariya ATH 中的一种优先对映选择性导向基团，因为催化剂的 η 6 -芳烃-CH 和BMIDA 中的 σ 键合氧原子。这项工作扩展了传统 ATH 的领域，并展示了其在解决对称合成挑战方面的巨大潜力。
• 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