2-(benzo[d][1,3]dioxol-5-yl)-N-benzylethan-1-amine | 68104-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(benzo[d][1,3]dioxol-5-yl)-N-benzylethan-1-amine
• 英文别名: N-Benzyl-3,4-methylendioxy-β-phenethylamin；(2-benzo[1,3]dioxol-5-yl-ethyl)-benzyl-amine；Cambridge id 5523444；2-(1,3-benzodioxol-5-yl)-N-benzylethanamine
• CAS: 68104-29-0
• 化学式: C₁₆H₁₇NO₂
• mdl: MFCD01653962
• 分子量: 255.316
• InChiKey: LNUIQALPIMYUQG-UHFFFAOYSA-N

物化性质

• 沸点：
  389.3±11.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzo[d][1,3]dioxol-5-yl)-N-benzylethan-1-amine 在 碘 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到N-Benzyl-4,5-methylendioxy-2-iod-β-phenethylamin
  参考文献：
  名称：

  A DIRECT IODINATION METHOD WITH IODINE AND SILVER TRIFLATE FOR THE SYNTHESIS OF SPECT AND PET IMAGING AGENT PRECURSORS

  摘要：

  A direct iodination method with iodine and silver triflate for the synthesis of SPECT and PET imaging agent precursors has been developed.

  DOI：

  10.1081/scc-100105877
• 作为产物：
  描述：

  胡椒乙胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-(benzo[d][1,3]dioxol-5-yl)-N-benzylethan-1-amine
  参考文献：
  名称：

  Synthesis and antihyperglycemic evaluation of various protoberberine derivatives

  摘要：

  Various berberine derivatives (2-17) were synthesized and their antihyperglycemic activities were evaluated in a model of beta-cell-membrane chromatography and a model of alloxan-induced diabetes mice. The results indicated that compounds 5 and 14 exhibited antihyperglycemic activity. Their structure-activity relationships were discussed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.045

文献信息

• Ruthenium Pybox-Catalyzed Enantioselective Intramolecular C–H Amination of Sulfamoyl Azides en Route to Chiral Vicinal Diamines
  作者：Xin Nie、Zihan Yan、Sergei Ivlev、Eric Meggers

  DOI：10.1021/acs.joc.0c02279

  日期：2021.1.1

  Enantioselective C(sp3)–H aminations allow an efficient access to nonracemic chiral amines. This work reports the catalytic asymmetric synthesis of chiral 1,2,5-thiadiazolidine-1,1-dioxides by an enantioselective ring-closing 1,5-C–H amination of sulfamoyl azides. The reaction is catalyzed by a recently introduced simple chiral ruthenium bis(oxazoline) (pybox) complex ( Angew. Chem. Int. Ed. 2020,

  对映选择性的C（sp 3）–H胺可有效地获得非外消旋手性胺。这项工作报告了通过氨磺酰氨基叠氮化物的对映选择性闭环1，5-CH胺催化的手性1,2,5-噻二唑烷-1,1-二氧化物的催化不对称合成。该反应通过一个最近推出的简单的手性钌双（恶唑啉）（pybox）配合物（催化的Angew。化学式中间体版 2020，59（12395）并以高达98％的收率和高达98％ee的价格提供环状5元磺酰胺产物（如果C–H键位于苄基位置）。力学实验支持逐步机制，其中中间的钌亚硝烯类物质引发1，5-氢原子转移，然后立即发生自由基反弹。环状磺酰胺产物是用于合成手性邻二胺的合适中间体，已为代表性实例证实。
• HOMOPIPERONY LAMINE COMPOUND AND USE THEREOF
  申请人：SINOCHEM CORPORATION

  公开号：US20150225378A1

  公开（公告）日：2015-08-13

  The invention discloses a homopiperony lamine compound which has a structural general formula I as follows as shown in the specification: wherein definitions of substituents in the formula are as shown in the specification. The compound shown as the general formula I has broad-spectrum bactericidal and insecticidal activity in the field of agriculture. The compound shown as the general formula I has a good prevention effect on various germs such as cucumber downy mildew, wheat powdery mildew, puccinia sorghi, rice blast and cucumber gray mold, and particularly, still has the good prevention and control effect on the cucumber downy mildew, the puccinia sorghi and the wheat powdery mildew at a lower dosage. At the same time, a part of compound has better insecticidal activity, and can be used for preventing and controlling various insect pests such as diamondback moths, myzus persicae, armyworms and tetranychus cinabarinus boisdu.

  该发明公开了一种具有如下结构通式I的吗啡啶胺化合物，其中通式中的取代基定义如说明书所示。所示通式I的化合物在农业领域具有广谱的杀菌和杀虫活性。所示通式I的化合物对黄瓜霜霉病、小麦白粉病、玉米锈病、水稻稻瘟病和黄瓜灰霉病等各种细菌具有良好的防治效果，特别是在较低剂量下对黄瓜霜霉病、玉米锈病和小麦白粉病仍具有良好的防治效果。同时，部分化合物具有更好的杀虫活性，可用于预防和控制菜青虫、桃蚜、军虫和赤蜘蛛等各种昆虫害虫。
• Asymmetric Substitution by Alkynyl Copper Driven Dearomatization and Rearomatization
  作者：Yu‐Ze Sun、Zi‐Yang Ren、Yuan‐Xiang Yang、Yang Liu、Guo‐Qiang Lin、Zhi‐Tao He

  DOI：10.1002/anie.202314517

  日期：2023.11.20

  Catalytic asymmetric transformations by dearomatization have developed into a widely applicable synthetic strategy, but heavily relied on the use of arenes bearing a heteroatom. In this case, the dearomatization is facilitated by the involvement of a p‐orbital electron of the heteroatom. Different from the conventional substrate‐dependent model, here we demonstrate that the activation by a d‐orbital electron of the transition‐metal center can serve as a driving force for dearomatization, and is applied to the development of a novel asymmetric alkynyl copper facilitated remote substitution reaction. A newly modified PyBox chiral ligand enables the construction of valuable diarylmethyl and triarylmethyl skeletons in high enantioselectivities. An unexpected tandem process involving sequential remote substitution/cyclization/1,5‐H shift leads to the formation of the enantioenriched C−N axis. A gram‐scale reaction and various downstream transformations highlight the robustness of this method and the potential transformations of the products. Preliminary mechanistic studies reveal a mononuclear Cu‐catalyzed remote substitution process.

  摘要脱芳烃催化不对称转化已发展成为一种广泛适用的合成策略，但主要依赖于使用带有一个杂原子的烷烃。在这种情况下，杂原子的 p 轨道电子的参与促进了脱芳香化。与传统的底物依赖模型不同，我们在此证明了过渡金属中心 d 轨道电子的激活可以作为脱芳香化的驱动力，并将其应用于新型不对称炔铜促进远程取代反应的开发。一种新修饰的 PyBox 手性配体能够以高对映选择性构建有价值的二芳基甲基和三芳基甲基骨架。一个意想不到的串联过程（包括连续的远程取代/环化/1,5-H 转变）导致了对映体富集的 C-N 轴的形成。克级反应和各种下游转化过程凸显了该方法的稳健性和产物的潜在转化能力。初步的机理研究揭示了一种单核铜催化的远程取代过程。
• Electrohydrogenation of Nitriles with Amines by Cobalt Catalysis
  作者：Tiantian Wang、Fangfang He、Wei Jiang、Jie Liu

  DOI：10.1002/anie.202316140

  日期：2024.2.12

  efficient electrocatalytic method for earth-abundant cobalt hydride generation through a sequence of cathodic reduction and protonation. The application of this molecular cobalt catalyst allows for electroreductive amination of nitriles to produce various secondary and tertiary amines, as well as deuterium isotope labeling applications from readily available deuterium source.

  本文报道了一种温和有效的电催化方法，通过一系列阴极还原和质子化来产生地球上丰富的氢化钴。这种分子钴催化剂的应用允许对腈进行电还原胺化以生产各种仲胺和叔胺，以及利用容易获得的氘源进行氘同位素标记应用。
• Synthesis and structure–activity relationships of berberine analogues as a novel class of low-density-lipoprotein receptor up-regulators
  作者：Peng Yang、Dan-Qing Song、Ying-Hong Li、Wei-Jia Kong、Yan-Xiang Wang、Li-Mei Gao、Shu-Yu Liu、Rui-Qiang Cao、Jian-Dong Jiang

  DOI：10.1016/j.bmcl.2008.07.005

  日期：2008.8

  Berberine (BBR, 1) is a novel cholesterol-lowering agent that up-regulates low-density-lipoprotein receptor (LDLR) expression through a mechanism different from that of statins. Because of the unique mode of action and good safety record, BBR provoked our interest to do structure modification at different domains for its cholesterol-lowering activity. Nineteen BBR analogues with substituents on the benzene ring D were synthesized in the present study. The analysis of structure-activity relationship (SAR) indicated that the two methoxyl groups in an ortho-distribution on this benzene ring afforded a good activity. Among the 19 analogues, compound 8j bearing a methoxyl at both 10- and 11-position showed an increased LDLR up-regulatory activity in respect to BBR, and therefore has been selected as a promising cholesterol-lowering drug candidate for further evaluation. (C) 2008 Elsevier Ltd. All rights reserved.