(2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)methanol | 1152514-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)methanol
• 英文别名: [2-(3,4-dihydro-1H-isoquinolin-2-yl)phenyl]methanol
• CAS: 1152514-66-3
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: SDXNKMSBMVGDIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)methanol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以59 %的产率得到4b,6,12,13-tetrahydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline
  参考文献：
  名称：

  基于芳炔和 CO2 的正式 [2 + 2 + 2] 成环反应得到四氢异喹啉稠合苯并恶嗪酮

  摘要：

  四氢异喹啉及其稠合多杂环是许多天然产物中常见的结构基序。在这项研究中，我们报告了一种高效、收敛的合成方法，通过结合 3,4-二氢异喹啉、CO 2和苯炔，通过三组分形式 [2 + 2 + 2] 成环过程构建四氢异喹啉稠合多杂环。值得注意的是，富电子的 3,4-二氢异喹啉和缺电子的苯炔在此环化中表现出更大的反应性。此外，该方法受益于聚合合成和二氧化碳的利用，为四氢异喹啉稠合多杂环的简便合成提供了有价值的策略，在新型有机分子的发现和开发中具有潜在的应用。

  DOI：

  10.1039/d3ob01147j
• 作为产物：
  描述：

  2-(3,4-dihydroisoquinolin-2(1H)-yl)benzaldehyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到(2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)methanol
  参考文献：
  名称：

  Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines

  摘要：

  1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.031

文献信息

• A Robust Palladium(II)-Porphyrin Complex as Catalyst for Visible Light Induced Oxidative CH Functionalization
  作者：Wai-Pong To、Yungen Liu、Tai-Chu Lau、Chi-Ming Che

  DOI：10.1002/chem.201203774

  日期：2013.4.26

  A series of palladium(II)–porphyrin complexes that display dual emissions with lifetimes up to 437 μs have been synthesized. Among the four complexes, PdF20TPP is an efficient and robust catalyst for photoinduced oxidative CH functionalization by using oxygen as terminal oxidant. α‐Functionalized tertiary amines were obtained in good to excellent yields by light irradiation (λ>400 nm) of a mixture

  已经合成了一系列显示双发射且寿命高达437μs的钯（II）-卟啉配合物。在这四种络合物，PDF 20 TPP为光致氧化℃的高效且健壮的催化剂通过使用氧气作为氧化剂终端ħ官能化。通过对PdF 20 TPP的混合物进行光辐照（λ > 400 nm），可以得到高至极好产率的α-官能化叔胺，叔胺和亲核试剂（氰化物，硝基甲烷，丙二酸二甲酯，亚磷酸二乙酯和丙酮）在有氧条件下。可以类似地制备分子内环化胺化合物的四个实例。光化学反应前后的紫外可见吸收光谱比较表明，PdF 20 TPP具有很高的耐受性（回收率> 95％）。PdF 20 TPP的实际应用已通过使用低催化剂负载量（0.01 mol％）并以10 mmol规模进行的光化学反应得以揭示。该PDF 20 TPP催化剂可以优异的收率使光诱导的硫化物氧化为亚砜。机理研究表明，光催化通过单线态氧氧化进行。
• Bis(2-methoxyethyl)ether promoted intramolecular acceptorless dehydrogenative coupling to construct structurally diverse quinazolinones by molecular oxygen
  作者：Rongrong Zhao、Simiaomiao Wen、Hao Fu、Mengna Liu、Qixing Liu、Haifeng Zhou

  DOI：10.1039/d1gc04581d

  日期：——

  A simple, efficient, and clean approach for the synthesis of diverse dihydroisoquinolino[2,1-a]quinazolinones, 2-aryl quinazolinones, and analogues through intramolecular acceptorless dehydrogenative coupling has been achieved. The combination of bis(2-methoxyethyl)ether and molecular oxygen was identified as a highly efficient system for this oxidative dehydrogenative coupling sequential transformation

  已经实现了一种通过分子内无受体脱氢偶联合成多种二氢异喹啉[ 2,1- a ]喹唑啉酮、2-芳基喹唑啉酮和类似物的简单、高效和清洁的方法。双（2-甲氧基乙基）醚和分子氧的组合被确定为这种氧化脱氢偶联顺序转化的高效体系，无需外部引发剂、催化剂和添加剂。通过29个例子的范围和克级反应证明了其适用性和实用性。还进行了一些对照实验以支持可能的反应途径。
• Intramolecular Dehydrative Coupling of Tertiary Amines and Ketones Promoted by KO-<i>t</i>-Bu/DMF: A New Synthesis of Indole Derivatives
  作者：Wen-tao Wei、Xue-jiao Dong、Shao-zhen Nie、Yan-yan Chen、Xue-jing Zhang、Ming Yan

  DOI：10.1021/ol402908m

  日期：2013.12.6

  A new synthesis of indole derivatives has been achieved through intramolecular dehydrative coupling of tertiary amines and ketones promoted by KO-t-Bu/DMF. The reaction probably proceeds via an α-amino alkyl radical pathway.

  通过KO- t- Bu / DMF促进的叔胺和酮的分子内脱水偶联，实现了吲哚衍生物的新合成。该反应可能通过α-氨基烷基自由基途径进行。
• Efficient Construction of CN Double Bonds<i>via</i>Acceptorless Dehydrogenative Coupling
  作者：Xiang Sun、Yu Hu、Shao-zhen Nie、Yun-yun Yan、Xue-jing Zhang、Ming Yan

  DOI：10.1002/adsc.201300455

  日期：2013.8.12

  AbstractThe efficient construction of CN double bonds has been achieved by the Ir‐catalyzed intramolecular acceptorless dehydrogenative cross‐coupling of tertiary amines and amides. An iridium/2‐hydroxypyridine complex was identified as the highly efficient catalyst. A number of quinazolinone derivatives was prepared in excellent yields. An iridium‐mediated CH activation mechanism is proposed. This finding provides an unprecedented strategy for the direct imidation of sp3 CH bonds.magnified image
• Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines
  作者：Cheryl L. Mathis、Brandi M. Gist、Conerd K. Frederickson、Katie M. Midkiff、Christopher C. Marvin

  DOI：10.1016/j.tetlet.2013.02.031

  日期：2013.4

  1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.