(R)-(+)-2-(1-naphthyl)-4-phenylbut-3-yn-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(+)-2-(1-naphthyl)-4-phenylbut-3-yn-2-ol
• 英文别名: (2R)-2-naphthalen-1-yl-4-phenylbut-3-yn-2-ol
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: HEFGHOFFJHWPLW-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1-萘乙酮 、 苯乙炔 在 titanium(IV) isopropylate benzene-1,3-bis-[(S)-SO₂NH-C(Bn)-C(Et)2-OH] 、 diethylzinc 作用下， 以 甲苯 为溶剂， 反应 121.0h， 生成 (R)-(+)-2-(1-naphthyl)-4-phenylbut-3-yn-2-ol 、 (S)-(-)-2-(1-naphthyl)-4-phenylbut-3-yn-2-ol
  参考文献：
  名称：

  新的C 2-对称的双磺酰胺配体的合成及其在炔醛与醛和酮的对映选择性加成中的应用

  摘要：

  新颖的C 2-对称双磺酰胺配体易于通过三个简单步骤制备，并用于炔基锌试剂对醛的对映选择性加成。发现化合物7a是该反应的杰出配体。当使用4mol％的7a的催化剂负载量时，在非常温和的条件下获得了ee值高达97％的高对映选择性。当配体7a的量降低至2mol％时，仍达到高达95％ee的优异对映体控制水平。迄今为止，已开发出最经济的催化剂体系，用于在配体负载和对映选择性方面向芳族醛中添加末端炔烃。此外，配体7a发现与Ti（O - Pr）4组合可以有效地促进炔基锌试剂在非常温和的条件下与未活化的简单酮的加成反应。得到相应的手性叔炔丙醇，其对映体过量最高为81％。

  DOI：

  10.1002/adsc.200505162

文献信息

• Lithium Binaphtholate-Catalyzed Asymmetric Addition of Lithium Acetylides to Carbonyl Compounds
  作者：Shunsuke Kotani、Kenji Kukita、Kana Tanaka、Tomonori Ichibakase、Makoto Nakajima

  DOI：10.1021/jo5005394

  日期：2014.6.6

  The asymmetric addition of lithium acetylides to carbonyl compounds in the presence of a chiral lithium binaphtholate catalyst was developed. A procedure involving the slow addition of carbonyl compounds to lithium acetylides improved the enantioselectivity. This reaction afforded diverse chiral secondary and tertiary propargylic alcohols in high yields and with good to high enantioselectivities.

  开发了在手性联萘甲酸锂催化剂存在下将乙炔化锂不对称加成到羰基化合物上的方法。涉及将羰基化合物缓慢添加至乙炔锂的方法提高了对映选择性。该反应以高收率和良好至高对映选择性提供了各种手性仲和叔炔丙醇。
• Highly Enantioselective Phenylacetylene Additions to Ketones Catalyzed by (<i>S</i>)-BINOL−Ti Complex
  作者：Yifeng Zhou、Rui Wang、Zhaoqing Xu、Wenjin Yan、Lei Liu、Yongfeng Kang、Zhijian Han

  DOI：10.1021/ol0485621

  日期：2004.11.1

  Ti(O(i)Pr)(4) is an effective chiral catalyst for the catalytic asymmetric addition of alkynylzinc to unactivated simple ketones. Good to excellent enantioselectivities were achieved. No previous case has been reported successfully using BINOL to catalyze the addition of phenylacetylene to unactivated ketones, and thus the utility of BINOL in asymmetric catalysis is expanded.

  容易获得且便宜的（S）-BINOL配体与Ti（O（i）Pr）（4）结合使用，是一种有效的手性催化剂，可将炔基锌催化不对称加成到未活化的简单酮上。实现了良好至优异的对映选择性。没有以前的案例成功报道过使用BINOL催化苯乙炔加成到未活化的酮上的情况，因此BINOL在不对称催化中的应用得到了扩展。
• Catalytic asymmetric addition of alkynylzinc reagents to ketones using polymer-supported chiral Schiff-base amino alcohols
  作者：Chao Chen、Liang Hong、Bangzhi Zhang、Rui Wang

  DOI：10.1016/j.tetasy.2007.11.040

  日期：2008.2

  Polymer-supported Schiff-base of optically active amino alcohols was used as chiral ligands in the enantioselective addition of alkynylzinc to simple ketones. At a 10 mol % ligand loading, chiral propargylic alcohols with moderate to good ee values (up to 89%) were produced. The polymeric catalyst could be recycled many times and used for further reactions.

  聚合物支撑的光学活性氨基醇的席夫碱用作手性配体，用于将炔基锌对映选择性加成至简单的酮中。在配体负载量为10 mol％的情况下，生产出具有中等至良好ee值（最高89％）的手性炔丙醇。聚合物催化剂可以循环多次并用于进一步的反应。
• Enantioselective Alkynylation of Aromatic Ketones Catalyzed by New Chiral Oxazolidine Ligands
  作者：Yong-Feng Kang、Lei Liu、Rui Wang、Yi-Feng Zhou、Wen-Jin Yan

  DOI：10.1002/adsc.200404278

  日期：2005.2

  New chiral oxazolidine ligands have been derived conveniently from natural amino acids in good yields. Their use in the enantioselective addition of phenylacetylene to aromatic ketones has been tested with the best ee being up to 88%. We provide a simple, practical and inexpensive method to generate chiral tertiary propargylic alcohols.

  新的手性恶唑烷配体已方便地从天然氨基酸中以高收率得到。已经测试了它们在将苯乙炔对映选择性加成到芳族酮中的用途，最佳ee高达88％。我们提供了一种简单，实用和廉价的方法来生成手性叔炔丙醇。
• Enantioselective alkynylation of aromatic ketones promoted by (S)-phenylalanine-derived β-amino alcohol
  作者：Lei Liu、Yong-feng Kang、Rui Wang、Yi-feng Zhou、Chao Chen、Ming Ni、Mao-zhen Gong

  DOI：10.1016/j.tetasy.2004.10.014

  日期：2004.11

  (S)-(-)-2-Amino-1,1,3-triphenylpropanol 3c, which is readily available from L-Phe, was found to be effective in catalyzing the addition reaction of an alkynylzinc reagent to aromatic ketones with up to 80% ee of the thus produced chiral tertiary propargylic alcohols. Unlike previous reports, 3c does not require the use of an additional central metal (other than zinc itself) and the prepreparation of an alkynylzinc. This has greatly simplified the experimental procedure for this reaction. (C) 2004 Elsevier Ltd. All rights reserved.