1-萘甲醇,a-苯基-,(S)- | 1517-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-萘甲醇,a-苯基-,(S)-
• 英文名称: (S)-1-naphthyl(phenyl)methanol
• 英文别名: (S)-naphthalen-1-yl(phenyl)methanol；naphthalen-1-yl(phenyl)methanol；(S)-α-naphthylphenylcarbinol；(1-naphthyl)phenylmethanol；(S)-1-naphthylphenylmethanol
• CAS: 1517-61-9
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: STUPJDVVIONFLI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  2-己炔酸 、 1-萘甲醇,a-苯基-,(S)- 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以35%的产率得到(S)-(naphthalen-1-yl)(phenyl)methyl hext-2-ynoate
  参考文献：
  名称：

  Palladium-Catalyzed Stereospecific Decarboxylative Benzylation of Alkynes

  摘要：

  Enantioenriched benzyl esters of propiolic acids undergo highly stereospecific decarboxylative coupling to provide 1,1-diarylethynyl methanes. This sp-sp(3) coupling does not require strongly basic conditions or preformed organometallics and produces CO2 as the sole byproduct. Ultimately, this method results in the successful transfer of stereochemical information from secondary benzyl alcohols to generate enantioenriched tertiary diarylmethanes.

  DOI：

  10.1021/acs.orglett.5b02410
• 作为产物：
  描述：

  ([1]naphthyl-phenyl-methyl)-carbamic acid ethyl ester 在 乙醚 、 potassium ethoxide 、 nitrous anhydride 、 丙酮 作用下， 生成 1-萘甲醇,a-苯基-,(S)-
  参考文献：
  名称：

  Aliphatic Diazo Compounds. II. Phenyl-alpha-naphthyldiazomethane

  摘要：

  DOI：

  10.1021/ja01296a015

文献信息

• The concise synthesis of chiral tfb ligands and their application to the rhodium-catalyzed asymmetric arylation of aldehydes
  作者：Takahiro Nishimura、Hana Kumamoto、Makoto Nagaosa、Tamio Hayashi

  DOI：10.1039/b911118b

  日期：——

  New C2-symmetric tetrafluorobenzobarrelene ligands were prepared and applied successfully to the rhodium-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes giving chiral diarylmethanols in high yield with high enantioselectivity.

  制备了新的C2对称的四氟苯并戊烯配体，并将其成功地用于铑催化的芳基硼酸向芳族醛的不对称加成反应，从而以高收率和高对映体选择性得到手性二芳基甲醇。
• Cobalt-Catalyzed Addition Reaction of Organoboronic Acids with Aldehydes: Highly Enantioselective Synthesis of Diarylmethanols
  作者：Jaganathan Karthikeyan、Masilamani Jeganmohan、Chien-Hong Cheng

  DOI：10.1002/chem.201001160

  日期：——

  Predicted outcomes: The addition reaction of organoboronic acids with aldehydes in the presence of K2CO3 catalyzed by CoI2/(R,R)‐BDPP gives chiral secondary alcohols in excellent yields with 90–99 % enantiomeric excess (see scheme; (R,R)‐BDPP=(2R,4R)‐(+)‐2,4‐bis(diphenylphosphino)pentane). This method provides an alternative to prepare an R and S enantiomeric pair by using the same chiral ligand and

  预期的结果：在CoI 2 /（R，R）-BDPP催化下，在存在K 2 CO 3的情况下，有机硼酸与醛的加成反应可得到出色的手性仲醇，对映体过量90-99％（参见方案；（R，R）-BDPP =（2 R，4 R）-（+）-2,4-双（二苯基膦基）戊烷）。该方法提供了另一种通过使用相同的手性配体制备R和S对映体对的方法，并且可以预测反应的立体化学结果。
• Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis
  作者：Zhiwu Lu、Haoyang Zhang、Zhiping Yang、Ning Ding、Ling Meng、Jun Wang

  DOI：10.1021/acscatal.8b04787

  日期：2019.2.1

  Asymmetric hydrophosphination is the most atomically economical and straightforward approach to the construction of chiral organophosphorus compounds. Good stereoselectivities have been achieved in asymmetric hydrophosphination of an electron-deficient C═C double bond, but substrates involving nonpolar C═C bonds remain difficult and are rarely tackled. Herein, we report asymmetric hydrophosphination

  不对称氢磷酸化是手性有机磷化合物构建中最原子经济且最直接的方法。在缺乏电子的C═C双键的不对称加氢磷化反应中已经获得了良好的立体选择性，但是涉及非极性C═C键的底物仍然很困难，而且很少解决。在本文中，我们报道了非电子活化的双键的非对称氢磷酸化，其立体控制程度非常高。该策略为制备高产率（高达99％的产率）和对映选择性（高达ee的99％）的叔膦提供了一个方便且广泛适用的平台。
• Highly Enantioselective Addition of In Situ Prepared Arylzinc to Aldehydes Catalyzed by a Series of Atropisomeric Binaphthyl-Derived Amino Alcohols
  作者：Gui Lu、Fuk Yee Kwong、Ji-Wu Ruan、Yue-Ming Li、Albert S. C. Chan

  DOI：10.1002/chem.200501048

  日期：2006.5.15

  catalyst, both enantiomers of many pharmaceutically interesting diarylmethanols can be obtained by the proper combination of various arylzinc reagents with different aldehydes; this catalytic system also works well for the phenylation of aliphatic aldehydes to give up to 96 % ee.

  用手性联萘衍生的氨基醇作为催化剂直接将原位制备的芳基锌加到醛中可以提供高收率和优异的对映选择性（高达99％ee，ee =对映体过量）的旋光二芳基甲醇。通过使用单一催化剂，可以通过将各种芳基锌试剂与不同的醛适当组合来获得许多可药用的二芳基甲醇的两种对映异构体。该催化体系也可以很好地用于脂族醛的苯基化反应，以产生高达96％的ee。
• Asymmetric diethylzinc addition and phenyl transfer to aldehydes using chiral cis-cyclopropane-based amino alcohols
  作者：Jiangchun Zhong、Hongchao Guo、Mingan Wang、Mingming Yin、Min Wang

  DOI：10.1016/j.tetasy.2007.03.006

  日期：2007.4

  A new series of amino alcohols with a chiral cyclopropane backbone have been developed and used in the catalytic asymmetric diethylzinc addition and phenyl transfer to various types of aldehydes. These cyclopropane-based chiral amino alcohols show high enantioselectivity in the addition of organozincs to aromatic and aliphatic aldehydes. For diethylzinc addition to aromatic and aliphatic aldehydes

  已经开发了具有手性环丙烷骨架的一系列新的氨基醇，并将其用于催化不对称二乙基锌的加成反应以及将苯基转移至各种类型的醛中。这些基于环丙烷的手性氨基醇在将有机锌添加到芳族和脂族醛中时显示出高对映选择性。对于将二乙基锌添加到芳族和脂族醛中，分别获得了高达97％ee和93％ee。对于将苯基转移到芳族醛中，最佳对映选择性为89％ee。