N-benzyl-1-(4’-cyanophenyl)ethylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-1-(4’-cyanophenyl)ethylamine
• 英文别名: N-benzyl-1-(4-cyanophenyl)ethylamine；4-[1-(Benzylamino)ethyl]benzonitrile
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: IOPGFXNJSMTLKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氰基苯乙酮 在 甲醇 、 titanium(IV) tetraethanolate 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 N-benzyl-1-(4’-cyanophenyl)ethylamine
  参考文献：
  名称：

  手性二氮杂膦烯催化不对称亚胺硼氢化反应

  摘要：

  对映选择性亚胺氢硼化已证明了二氮杂膦烯作为手性催化剂的首次使用。已证明，由市售材料通过简单的三步合成方法制备的手性二氮杂ol烯具有最高的对映选择性，迄今为止，据报道该化合物与频哪醇硼烷一起对烷基亚胺进行硼氢化。在低（2 mol％）催化剂负载下，可获得高达88:12的对映体比例。显示了使用这种主要基团催化方案进行不对称还原的20个实例，包括药物对雷沙吉兰和芬迪林的合成。

  DOI：

  10.1002/anie.201709926

文献信息

• Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes
  作者：Matt R. Adams、Chieh-Hung Tien、Robert McDonald、Alexander W. H. Speed

  DOI：10.1002/anie.201709926

  日期：2017.12.22

  first use of diazaphospholenes as chiral catalysts has been demonstrated with enantioselective imine hydroboration. A chiral diazaphospholene prepared in a simple three‐step synthesis from commercial materials has been shown to achieve the highest enantioselectivity for the hydroboration of alkyl imines with pinacolborane reported to date. Enantiomer ratios of up to 88:12 were obtained with low (2 mol %)

  对映选择性亚胺氢硼化已证明了二氮杂膦烯作为手性催化剂的首次使用。已证明，由市售材料通过简单的三步合成方法制备的手性二氮杂ol烯具有最高的对映选择性，迄今为止，据报道该化合物与频哪醇硼烷一起对烷基亚胺进行硼氢化。在低（2 mol％）催化剂负载下，可获得高达88:12的对映体比例。显示了使用这种主要基团催化方案进行不对称还原的20个实例，包括药物对雷沙吉兰和芬迪林的合成。
• Chiral catalyst and method for asymmetric reduction of an imine
  申请人：DALHOUSIE UNIVERSITY

  公开号：US11161863B2

  公开（公告）日：2021-11-02

  The present disclosure discusses (i) a compound having a chemical formula according to Formula (I), or its enantiomer; and (ii) a compound that is reactive with a hydride to produce a compound having a chemical formula according to Formula (I), or its enantiomer. Formula (I) is: Formula (I) where R1 and R2 are H, optionally substituted C1-C3 alkyl, or linked together to form an optionally substituted C3 or C4 alkyl group; R3 and R3′ are H; R4 and R4′ are the same, and are optionally substituted C1-C6 alkyl; and R5 and R5′ are the same, and are optionally substituted aryl or heteroaryl. In some examples, R4 and R5 are linked, and R4′ and R5′ are linked, where both linking groups are the same. The present disclosure also discusses methods of asymmetric reduction of an imine, and methods of forming the catalysts and pre-catalysts.

  本公开讨论(i)具有化学式为式(I)的化合物或其对映体；以及(ii)与氢化物反应生成具有化学式为式(I)的化合物或其对映体的化合物。式（I）为式 (I) 其中 R1 和 R2 是 H、任选取代的 C1-C3 烷基或连接在一起形成任选取代的 C3 或 C4 烷基；R3 和 R3′ 是 H；R4 和 R4′ 相同，是任选取代的 C1-C6 烷基；R5 和 R5′ 相同，是任选取代的芳基或杂芳基。在某些实例中，R4 和 R5 连接，R4′ 和 R5′ 连接，其中两个连接基团相同。本公开还讨论了亚胺的不对称还原方法，以及形成催化剂和前催化剂的方法。
• CHIRAL CATALYST AND METHOD FOR ASYMMETRIC REDUCTION OF AN IMINE
  申请人：DALHOUSIE UNIVERSITY

  公开号：US20200255463A1

  公开（公告）日：2020-08-13

  The present disclosure discusses (i) a compound having a chemical formula according to Formula (I), or its enantiomer; and (ii) a compound that is reactive with a hydride to produce a compound having a chemical formula according to Formula (I), or its enantiomer. Formula (I) is: Formula (I) where R 1 and R 2 are H, optionally substituted C 1 -C 3 alkyl, or linked together to form an optionally substituted C 3 or C 4 alkyl group; R 3 and R 3 ′are H; R 4 and R 4 ′ are the same, and are optionally substituted C 1 -C 6 alkyl; and R 5 and R 5 ′ are the same, and are optionally substituted aryl or heteroaryl. In some examples, R4 and R5 are linked, and R 4 ′ and R 5 ′ are linked, where both linking groups are the same. The present disclosure also discusses methods of asymmetric reduction of an imine, and methods of forming the catalysts and pre-catalysts.
• Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes
  作者：Chieh-Hung Tien、Matt R. Adams、Michael J. Ferguson、Erin R. Johnson、Alexander W. H. Speed

  DOI：10.1021/acs.orglett.7b02695

  日期：2017.10.20

  shown to catalyze the 1,2 hydroboration of 19 imines, and three α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.

  1,2,4,3-三氮杂膦烯（TAPs）的合成和催化活性的报道。与以前报道的二氮杂膦烯相比，TAP代表了更模块化的支架。TAP卤化物已显示可与频哪醇硼烷催化19个亚胺和3个α，β不饱和醛的1,2加氢硼化反应，包括先前未报道的重氮磷腈系统未进行氢硼化反应的实例。DFT计算支持三氮杂磷腈阳离子与底物相互作用的机理，该机理不同于二氮杂磷腈催化的硼氢化反应。