N-(3,4-dihydronaphthalen-1(2H)-ylidene)-1-phenylmethanamine | 32851-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-(3,4-dihydronaphthalen-1(2H)-ylidene)-1-phenylmethanamine
• 英文别名: N-benzyl-tetraloneketimine；N-benzyl-3,4-dihydro-2H-naphthalen-1-imine
• CAS: 32851-51-7
• 化学式: C₁₇H₁₇N
• 分子量: 235.329
• InChiKey: UIVYFEUNUWXYEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3,4-dihydronaphthalen-1(2H)-ylidene)-1-phenylmethanamine 在 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 2'-benzylspiro[2,3-dihydro-1H-naphthalene-4,3'-isoindole]-1'-one
  参考文献：
  名称：

  通过芳基自由基引发的1,6-环化形成的异喹啉骨架

  摘要：

  发生独家1,6-环化，得到当烯酰胺和带有烯胺底物异喹啉框架外的α-烯烃部分用三-处理Ñ在自由基引发剂（存在-butyltin氢化9A，B →图12A，B ; 13A，B → 18a，b）。另一方面，当在相同条件下（22a，b → 26a，b和26）处理带有内烯烃部分的酰胺底物时，竞争性的1,6-和1,5-环化反应产生了异喹诺酮和异吲哚酮骨架的混合物。27a，b）。

  DOI：

  10.1016/0040-4039(90)80216-9
• 作为产物：
  描述：

  N-mono(pinacolboryl)benzylamine 在 水 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 N-(3,4-dihydronaphthalen-1(2H)-ylidene)-1-phenylmethanamine
  参考文献：
  名称：

  Taking the F out of FLP: Simple Lewis Acid–Base Pairs for Mild Reductions with Neutral Boranes via Borenium Ion Catalysis

  摘要：

  Discrete three-coordinate borenium salts 1c and 1d are accessed by cooperative Lewis acid-base pair-mediated heterolytic splitting of the B-H bond in pinacolborane by B(C6F5)(3)center dot DABCO and Ph3C+/DABCO, respectively. The resulting salts are competent catalysts in the reduction of a broad range of imines and can be generated in situ. Moreover, a mechanistic framework for borenium catalysis based on experimental evidence is proposed. The reaction is suggested to proceed by borenium activation of the imine substrate followed by counterintuitive hydride delivery from HBPin (with the assistance of DABCO) rather than from the HB(C6F5)(3)(-) anion, contrary to typical mechanisms of reduction in FLP systems.

  DOI：

  10.1021/ja307374j

文献信息

• RUTHENIUM-DIAMINE COMPLEX AND METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND
  申请人：Touge Taichiro

  公开号：US20140051871A1

  公开（公告）日：2014-02-20

  Provided is a ruthenium complex that is represented by general formula (1*) and is useful as an asymmetric reduction catalyst. (In the formula, * is an asymmetric carbon atom; R 1 is an arenesulfonyl group, and the like; R 2 and R 3 are a phenyl group, and the like; R 10 through R 14 are selected from a hydrogen atom, C 1-10 alkyl group, and the like, but R 10 through R 14 are not simultaneously hydrogen atoms; X is a halogen atom and the like; j and k are each either 0 or 1; and j+k is 0 or 2.)

  提供一个钌配合物，其由通式(1*)表示，可用作不对称还原催化剂。 (在公式中，*是不对称碳原子；R1是芳基磺酰基团等；R2和R3是苯基团等；R10至R14选自氢原子、C1-10烷基团等，但R10至R14不同时为氢原子；X是卤素原子等；j和k都是0或1；j+k为0或2。)
• Solvent-Free Synthesis of Racemic α-Aminonitriles
  作者：Carmen Nájera、Alejandro Baeza、José Sansano

  DOI：10.1055/s-2007-965974

  日期：2007.4

  A very simple one-step, environmentally friendly procedure for the synthesis of α-aminonitriles from aldehydes and ketones, using trimethylsilyl cyanide in the absence of solvent, is reported. The active catalyst of this three-component (Strecker) reaction was the amine employed in the transformation. In general, aldehydes react more rapidly than ketones and give almost quantitative yields of the corresponding α-aminonitriles in less than fifteen minutes. However, only cyclic ketones afford the corresponding α-aminonitriles in excellent chemical yields under these conditions.

  报道了一种非常简单的单步环境友好型方法，通过在无溶剂条件下使用三甲基硅烷腈，从醛和酮合成α-氨基腈。该三组分（Strecker）反应的活性催化剂是用于转化反应的胺。通常情况下，醛比酮反应更快，在不到十五分钟内即可几乎定量地生成相应的α-氨基腈。然而，在这些条件下，只有环状酮能以优异的化学产率生成相应的α-氨基腈。
• Asymmetric transfer hydrogenation of imines catalyzed by a polymer-immobilized chiral catalyst
  作者：Naoki Haraguchi、Keiichi Tsuru、Yukihiro Arakawa、Shinichi Itsuno

  DOI：10.1039/b815407b

  日期：——

  The asymmetric transfer hydrogenation of imines was performed with the use of a polymer-immobilized chiral catalyst. The chiral catalyst, prepared from crosslinked polystyrene-immobilized chiral 1,2-diamine monosulfonamide, was effective in the asymmetric transfer hydrogenation of N-benzyl imines in CH2Cl2 to give a chiral amine in high yield and good enantioselectivity. Furthermore, an amphiphilic

  亚胺的不对称转移氢化是利用聚合物固定的手性催化剂进行的。由交联的聚苯乙烯固定的手性1,2-二胺单磺酰胺制备的手性催化剂可有效地在CH 2 Cl 2中对N-苄基亚胺进行不对称转移氢化，从而以高收率和良好的对映选择性得到手性胺。此外，由含磺化基团的交联聚苯乙烯制备的两亲聚合物催化剂成功催化了环亚胺的不对称转移加氢反应。水。通过使用聚合物催化剂，可以得到具有高达94％ee的对映体富集的仲胺。
• Pd(OAc)₂-Catalyzed Carbonylation of Amines
  作者：Kazuhiko Orito、Mamoru Miyazawa、Takatoshi Nakamura、Akiyoshi Horibata、Harumi Ushito、Hideo Nagasaki、Motoki Yuguchi、Satoshi Yamashita、Tetsuro Yamazaki、Masao Tokuda

  DOI：10.1021/jo060612n

  日期：2006.8.1

  phenethylamine derivatives, underwent a direct aromatic carbonylation to afford five- or six-membered benzolactams. In the carbonylation, the chelation effect or steric repulsion between Pd(II) and the meta-substituent in the ortho-palladation and the ring sizes of cyclopalladation products that were formed prior to carbonylation were found to generate good site selectivity and increase the reaction rate. In

  无膦的催化体系[Pd（OAc）2 -Cu（OAc）2-空气]在沸腾的甲苯中，在CO气体（1个大气压）下引发了胺的底物特异性羰基化。通过伯胺的羰基化获得对称的N，N'-二烷基脲。N，N，N′-三烷基脲通过向上述反应容器中添加仲胺而选择性地形成。仲胺不产生四烷基脲。但是，在烷基链上带有苯基的二烷基胺，例如N-对单烷基化的苄胺或苯乙胺衍生物进行直接的芳族羰基化反应，得到五元或六元的苯并内酰胺。在羰基化反应中，发现Pd（II）与邻位钯的间位取代基之间的螯合效应或位阻以及羰基化之前形成的环钯的产物的环大小可产生良好的位点选择性并提高反应速率。相反，具有羟基的ω-芳基烷基胺的羰基化既不产生脲也没有苯并内酰胺，而是平稳地产生1，3-恶唑烷酮。在所用条件下，胺的盐酸盐也进行羰基化，得到相应的酰胺。该程序使得可以制备氨基酸酯的脲和实际收率的N-烷基氨基甲酸酯。
• [EN] RUTHENIUM-DIAMINE COMPLEXES AND METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUNDS<br/>[FR] COMPLEXES RUTHÉNIUM-DIAMINE ET PROCÉDÉ DE PRODUCTION DE COMPOSÉS OPTIQUEMENT ACTIFS
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2012026201A1

  公开（公告）日：2012-03-01

  Provided is a catalyst for asymmetric reduction, which can be produced by a convenient and safe production method, has a strong catalytic activity, and has excellent stereoselectivity. The present invention relates to a ruthenium complex represented by the following formula (1): wherein R1 represents an alkyl group or the like; Y represents a hydrogen atom; X represents a halogen atom or the like; j and k each represent 0 or 1; R2 and R3 each represent an alkyl group or the like; R11 to R19 each represent a hydrogen atom, an alkyl group or the like; Z represents oxygen or sulfur; n1 represents 1 or 2; and n2 represents an integer from 1 to 3, a method for producing the ruthenium complex, a catalyst for asymmetric reduction formed from the ruthenium complex, and methods for selectively producing an optically active alcohol and an optically active amine using the catalyst for asymmetric reduction.

  提供了一种用于不对称还原的催化剂，可以通过一种方便且安全的生产方法生产，具有强大的催化活性，并具有优异的立体选择性。本发明涉及一种由以下式（1）表示的钌配合物：其中R1代表烷基或类似物；Y代表氢原子；X代表卤原子或类似物；j和k各自代表0或1；R2和R3各自代表烷基或类似物；R11至R19各自代表氢原子、烷基或类似物；Z代表氧或硫；n1代表1或2；n2代表从1到3的整数，一种制备钌配合物的方法，由钌配合物形成的不对称还原催化剂，以及使用该不对称还原催化剂选择性地制备光学活性醇和光学活性胺的方法。