naphthalen-2-yl(2-(pyridin-2-yl)phenyl)methanol | 1404120-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: naphthalen-2-yl(2-(pyridin-2-yl)phenyl)methanol
• 英文别名: Naphthalen-2-yl-(2-pyridin-2-ylphenyl)methanol；naphthalen-2-yl-(2-pyridin-2-ylphenyl)methanol
• CAS: 1404120-25-7
• 化学式: C₂₂H₁₇NO
• 分子量: 311.383
• InChiKey: ANYLFWITGQHNKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  naphthalen-2-yl(2-(pyridin-2-yl)phenyl)methanol 在 silver hexafluoroantimonate 、 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以84%的产率得到2-苯基吡啶
  参考文献：
  名称：

  Cobalt(III)-Catalyzed Functionalization of Unstrained Carbon–Carbon Bonds through β-Carbon Cleavage of Alcohols

  摘要：

  We demonstrate that a simple Co(III)-complex can efficiently catalyze the cleavage of unstrained C-C bonds via the beta-carbon elimination of secondary and tertiary alcohols bearing a directing group. The cobalt-aryl intermediate generated under the reaction conditions can be trapped by different electrophiles to generate a new carbon carbon bond. Some essential features of this new Co-based mechanistic manifold were revealed by preliminary mechanistic studies.

  DOI：

  10.1021/acscatal.5b01753
• 作为产物：
  描述：

  2-苯基吡啶 、 2-萘甲醛 在 Dimethylzinc 、 [Mn(CO)₄Br]₂ 、 zinc dibromide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 以87 %的产率得到naphthalen-2-yl(2-(pyridin-2-yl)phenyl)methanol
  参考文献：
  名称：

  二聚锰催化的 C(sp2)-H 键与惰性醛的直接亲核加成

  摘要：

  已经开发了由二聚锰催化的 C(sp 2 )-H 键与醛的有效直接亲核加成反应。该反应具有广泛的底物范围，并且以惰性脂肪醛作为底物也获得了高产率。二聚体Mn 2 (CO) 8 Br 2被证明是比单体Mn(CO) 5 Br 更有效的催化剂前体。

  DOI：

  10.1021/acs.joc.2c01908

文献信息

• Reductive Cleavage of the C sp 2C sp 3 Bond of Secondary Benzyl Alcohols: Rhodium Catalysis Directed by N-Containing Groups
  作者：Kang Chen、Hu Li、Zhi-Quan Lei、Yang Li、Wen-He Ye、Li-Sheng Zhang、Jian Sun、Zhang-Jie Shi

  DOI：10.1002/anie.201204338

  日期：2012.9.24

  1,1‐Biarylmethanol substrates undergo reductive cleavage of the CC bond in the presence of a cationic RhIII catalyst and H2 (see scheme; DG=directing group). Various functional groups are tolerated in the reaction system. Preliminary studies indicate that a five‐membered rhodacycle intermediate, which then converts into a RhIII hydride species for the reduction, is involved in the catalytic cycle.

  切割松动：1,1- Biarylmethanol基板经历作为C还原裂解 C键在阳离子铑的存在III催化剂和H 2（参见方案; DG =引导组）。在反应系统中可以容忍各种官能团。初步研究表明，五元的rhodocycle中间体参与催化循环，然后将其转化为Rh III氢化物进行还原。
• Rhodium(III)‐Catalyzed Aryl Borrowing Amination of Diaryl Methanols Containing Pyridine‐Directing Groups
  作者：Zheng‐Qiang Liu、Jing Tao、Xin Zhuang、Chuan‐Ming Hong、Zhen Luo、Yu‐Fei Wu、Qing‐Hua Li、Tang‐Lin Liu

  DOI：10.1002/adsc.202100772

  日期：2021.12.7

  The rhodium(III)-catalyzed aryl borrowing amination of various diaryl methanols with sulfonamides have been developed. The amination of alcohols via C−C bond activation is less developed and remains a challenge. These aryl borrowing reactions feature mild reaction conditions, good functional group tolerance, and compatibility with a wide range of alcohols, overall comprising an atom- and step-economic

  已经开发了铑 (III) 催化的各种二芳基甲醇与磺酰胺的借芳基胺化反应。通过 C-C 键活化对醇进行胺化作用尚不成熟，仍然是一个挑战。这些芳基借用反应具有反应条件温和、官能团耐受性好、与多种醇类相容性好等特点，总体上是一个原子经济和步骤经济的过程。机理研究表明，在芳基借用胺化反应过程中存在红环络合物。
• Silver catalyzed pyridine‐directed acceptorless dehydrogenation of secondary alcohols
  作者：Xin Zhuang、Jing Tao、Zhen Luo、Chuan‐Ming Hong、Zheng‐Qiang Liu、Qing‐Hua Li、Li‐Qing Ren、Qun‐Li Luo、Tang‐Lin Liu

  DOI：10.1002/jccs.202000517

  日期：2021.2

  A silver catalyzed pyridine‐directed acceptorless dehydrogenation of secondary benzyl alcohols was developed. This general procedure delivers ketones with high atom‐economy and hydrogen was the sole byproduct. This dehydrogenation reaction has a good functional group tolerance and high efficiency (up to 90% yield and 10,000/1 substrates‐to‐catalyst ratio).

  开发了一种银催化的吡啶定向的仲苄醇无受体脱氢剂。该通用程序可提供具有高原子经济性的酮，而氢是唯一的副产物。该脱氢反应具有良好的官能团耐受性和高效率（产率高达90％，底物与催化剂的比例为10,000 / 1）。
• Ruthenium(II)-Catalyzed Grignard-Type Nucleophilic Addition of C(sp²)–H Bonds to Unactivated Aldehydes
  作者：Lidong Yang、Zezhao Liu、Tingyu Tang、Shibiao Tang、Bin Li、Baiquan Wang

  DOI：10.1021/acs.joc.2c02039

  日期：2022.11.4

  The Grignard-type nucleophilic addition of C(sp2)–H bonds to aldehydes catalyzed by high-oxidation-state transition metal complexes is limited to activated aldehydes. Herein, we report the first example of Grignard-type nucleophilic addition of C(sp2)–H bonds to unactivated aldehydes catalyzed by high-oxidation-state ruthenium(II). The reaction has mild reaction conditions and good functional group

  由高氧化态过渡金属配合物催化的 C(sp 2 )-H 键与醛的格氏亲核加成仅限于活化的醛。在此，我们报道了高氧化态钌 (II) 催化的 C(sp 2 )-H 键与未活化醛的格氏型亲核加成的第一个例子。该反应反应条件温和，官能团耐受性好。以良好至极好的收率获得相应的醇产品。
• Cobalt(III)-Catalyzed Functionalization of Unstrained Carbon–Carbon Bonds through β-Carbon Cleavage of Alcohols
  作者：Erhan Ozkal、Bastien Cacherat、Bill Morandi

  DOI：10.1021/acscatal.5b01753

  日期：2015.11.6

  We demonstrate that a simple Co(III)-complex can efficiently catalyze the cleavage of unstrained C-C bonds via the beta-carbon elimination of secondary and tertiary alcohols bearing a directing group. The cobalt-aryl intermediate generated under the reaction conditions can be trapped by different electrophiles to generate a new carbon carbon bond. Some essential features of this new Co-based mechanistic manifold were revealed by preliminary mechanistic studies.