Benzyl-[1-(3-chloro-phenyl)-meth-(E)-ylidene]-amine | 180069-52-7

• 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: Benzyl-[1-(3-chloro-phenyl)-meth-(E)-ylidene]-amine
• CAS: 180069-52-7
• 化学式: C₁₄H₁₂ClN
• 分子量: 229.709
• InChiKey: NODJKHFCKDSWNG-LFIBNONCSA-N

物化性质

• 沸点：
  348.1±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 Benzyl-[1-(3-chloro-phenyl)-meth-(E)-ylidene]-amine 在 titanium(IV) isopropylate chiral-β-aminoalcohol 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以98%的产率得到Benzylamino-(3-chloro-phenyl)-acetonitrile
  参考文献：
  名称：

  N-水杨基-β-氨基醇作为催化不对称斯特雷克反应的新型配体

  摘要：

  描述了使用衍生自结构简单的手性N-水杨基-β-氨基醇的新型手性钛络合物催化剂的对映选择性Strecker合成。在催化剂（10mol％）存在下，N-亚苄基苄胺与三甲基甲硅烷基氰的反应以良好或优异的产率得到相应的α-氨基腈，同时具有相对高的对映选择性（至多86％ee）。与衍生自芳族醛的各种亚胺的类似反应导致中等至良好的对映选择性（44-81％ee）。

  DOI：

  10.1016/s0040-4039(03)00735-4
• 作为产物：
  描述：

  3-氯苯甲醛 、 苄胺 在 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到Benzyl-[1-(3-chloro-phenyl)-meth-(E)-ylidene]-amine
  参考文献：
  名称：

  Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines:  Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

  摘要：

  Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.

  DOI：

  10.1021/ja0494398

文献信息

• Diastereoselective Synthesis of <i>syn</i>-β-Lactams Using Rh-Catalyzed Reductive Mannich-Type Reaction of α,β-Unsaturated Esters
  作者：Motoyuki Isoda、Kazuyuki Sato、Masato Funakoshi、Keiko Omura、Atsushi Tarui、Masaaki Omote、Akira Ando

  DOI：10.1021/acs.joc.5b01233

  日期：2015.8.21

  The combination of Et2Zn and RhCl(PPh3)3 led to the facile generation of a rhodium–hydride complex (Rh–H) that catalyzed the 1,4-reduction of α,β-unsaturated esters. The resulting rhodium enolate performed as a Reformatsky-type reagent and reacted with various imines to give syn-β-lactams in good to excellent yields with high diastereoselectivity.

  Et 2 Zn和RhCl（PPh 3）3的组合导致容易生成铑-氢化物络合物（Rh-H），该络合物催化α，β-不饱和酯的1,4-还原。所得的烯醇铑作为Reformatsky型试剂起作用，并与各种亚胺反应，以良好的非对映异构体收率以优异的产率得到合成的-β-内酰胺。
• Regioselective cyclomanganation of Schiff bases. An unexpected effect of chloro substituents
  作者：Joan Albert、J. Magali Cadena、Jaume Granell、Xavier Solans、Mercè Font-Bardia

  DOI：10.1016/j.jorganchem.2004.07.010

  日期：2004.12

  In this paper we describe the synthesis of new metallacycles by the cyclomanganation reaction of benzyl-benzylidene-amines by using [MnMe(CO)(5)] as metallating agent. These ligands can undergo metallation on different aromatic carbon atoms but no important differences have been found in the regioselectivity of the process, that can be related to the electronic effect of the substituents. and in all the cases studied the endo-cyclomanganated complexes of para-substituted imines have been obtained. The corresponding exo-metallacycles were obtained by reaction of [MnMe(CO)(5)] on the imine 2.6-Ch(2)C(6)H(3)CH=NCH2Ph and 2,4,6-Me(3)C(6)Hr(2) -CH=NCH2Ph, derived from 2,6-dichlorobenzaldehyde and 2,4,6-trimethylbenzaldehyde, respectively.The results described suggest that the mechanism of the cyclomanganation is similar to that of cyclopalladation and it can be proposed that cyclomanganation takes place by the formation of a four-centered transition state, involving the C-H and Mn-C-acetyl bonds in the acetyl coordination complex formed in the first step of the reaction. (C) 2004 Elsevier B.V. All rights reserved.
• Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines:  Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids
  作者：Guy D. Joly、Eric N. Jacobsen

  DOI：10.1021/ja0494398

  日期：2004.4.1

  Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.
• N-Salicyl-β-aminoalcohols as a new class of ligand for catalytic asymmetric Strecker reactions
  作者：Woraluk Mansawat、Worawan Bhanthumnavin、Tirayut Vilaivan

  DOI：10.1016/s0040-4039(03)00735-4

  日期：2003.5

  An enantioselective Strecker synthesis employing novel chiral titanium complex catalysts derived from structurally simple chiral N-salicyl-β-amino alcohols is described. Reactions of N-benzylidenebenzylamine with trimethylsilyl cyanide in the presence of the catalyst (10 mol%) gave the corresponding α-aminonitrile in good to excellent yields, along with relatively high enantioselectivity (up to 86%

  描述了使用衍生自结构简单的手性N-水杨基-β-氨基醇的新型手性钛络合物催化剂的对映选择性Strecker合成。在催化剂（10mol％）存在下，N-亚苄基苄胺与三甲基甲硅烷基氰的反应以良好或优异的产率得到相应的α-氨基腈，同时具有相对高的对映选择性（至多86％ee）。与衍生自芳族醛的各种亚胺的类似反应导致中等至良好的对映选择性（44-81％ee）。