meso-1,2-bis(2-methoxyphenyl)ethylenediamine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: meso-1,2-bis(2-methoxyphenyl)ethylenediamine
• 英文别名: N,N'-(1,2-bis(2-methoxyphenyl)ethane-1,2-diyl)dibenzamide；1,2-Bis(2-methoxyphenyl)-1,2-ethanediamine；1,2-bis(2-methoxyphenyl)ethane-1,2-diamine
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: CTMKVJFFLNHDQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  meso-1,2-bis(2-methoxyphenyl)ethylenediamine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2,2'-(1,2-二氨基-1,2-乙二基)二苯酚
  参考文献：
  名称：

  Synthesis and evaluation of the anti-mammary tumor activity and of the estrogenic side effects of [1,2-bis(2,6-dihalo-3-hydroxyphenyl)ethylenediamine]platinum(II) complexes

  摘要：

  The synthesis and structural characterization of mammary tumor-inhibiting, diastereomeric [1,2-bis(2,6-dihalo-3-hydroxyphenyl) ethylenediamine]platinum(II) complexes with 2,6-Cl2, 2-F, 6-Cl, 2-Cl, 6-F and 2,6-F2 substituents (1-PtSO4 to 4-PtSO4) are described. The related 1,2-diphenylethylenediamines (1-4) are synthesized by stereoselective meso-meso and D,L-D,L diaza-Cope-rearrangement reactions and coordinated to platinum(II) with K2PtI4 (1-PtI2 to 4-PtI2). The subsequent reaction with Ag2SO4 leads to the respective sulfatoplatinum(II) complexes. They were tested for their anti-tumor activities on die hormone-sensitive and- insensitive MXT mammary carcinoma implanted in mice (MXT-MC, ER+ and MXT-MC, ER-). Complexes with F atoms in the neighborhood of the 3-hydroxy group showed strong inhibitory effects on the MXT-MC, ER+. The best effects were found for the diastereomeric 2,6-F2-substituted complexes, meso-4-PtSO4 and D,L-4-PtSO4. These complexes are strongly active both on the MXT-MC, ER+ and the MXT-MC, ER- and cause no estrogenic side effects.

  DOI：

  10.1016/0223-5234(93)90003-w
• 作为产物：
  描述：

  meso-N,N'-bis(2-hydroxybenzyliden)1,2-bis(2-methoxyphenyl)ethylenediamine 在 硫酸 作用下， 以93%的产率得到meso-1,2-bis(2-methoxyphenyl)ethylenediamine
  参考文献：
  名称：

  Synthesis and evaluation of the anti-mammary tumor activity and of the estrogenic side effects of [1,2-bis(2,6-dihalo-3-hydroxyphenyl)ethylenediamine]platinum(II) complexes

  摘要：

  The synthesis and structural characterization of mammary tumor-inhibiting, diastereomeric [1,2-bis(2,6-dihalo-3-hydroxyphenyl) ethylenediamine]platinum(II) complexes with 2,6-Cl2, 2-F, 6-Cl, 2-Cl, 6-F and 2,6-F2 substituents (1-PtSO4 to 4-PtSO4) are described. The related 1,2-diphenylethylenediamines (1-4) are synthesized by stereoselective meso-meso and D,L-D,L diaza-Cope-rearrangement reactions and coordinated to platinum(II) with K2PtI4 (1-PtI2 to 4-PtI2). The subsequent reaction with Ag2SO4 leads to the respective sulfatoplatinum(II) complexes. They were tested for their anti-tumor activities on die hormone-sensitive and- insensitive MXT mammary carcinoma implanted in mice (MXT-MC, ER+ and MXT-MC, ER-). Complexes with F atoms in the neighborhood of the 3-hydroxy group showed strong inhibitory effects on the MXT-MC, ER+. The best effects were found for the diastereomeric 2,6-F2-substituted complexes, meso-4-PtSO4 and D,L-4-PtSO4. These complexes are strongly active both on the MXT-MC, ER+ and the MXT-MC, ER- and cause no estrogenic side effects.

  DOI：

  10.1016/0223-5234(93)90003-w

文献信息

• Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron
  作者：Mingkang Zhou、Kaidi Li、Dongping Chen、Ronghua Xu、Guangqing Xu、Wenjun Tang

  DOI：10.1021/jacs.0c04558

  日期：2020.6.10

  We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method

  我们在此报告了一种通用、实用且高效的方法，通过手性二硼模板化的亚胺的还原偶联不对称合成各种手性邻二胺。该协议具有高对映选择性和立体特异性、温和的反应条件、简单的操作程序、使用现成的起始材料和广泛的底物范围。该方法表明了启用二硼的 [3,3]-σ 重排的普遍性。
• Sinomenine derivatives with embedment of nitrogen-containing heterocycles exhibiting potent TNF-αinhibitory activity
  作者：Meng Wang、LiYan Ma、YangTong Lou、Chao Bian、TingTing Zhou、HaiBin Zhou、HongZe Liao、Zhao Ma、DongSheng Yin、AiZhong Chen、ShaoZhong Wang、ZhenYu Yang、Bing Sun、ZhuJun Yao

  DOI：10.1007/s11426-012-4588-8

  日期：2012.12

  Inhibitory effect on tumor necrosis factor-α (TNF-α) production by sinomenine derivatives with embedment of small drug-like nitrogen hetereocyclic moieties has been studied in this work. Several new sinomenine derivatives having chlorophenyl substituent have been found to exhibit much more potent TNF-α inhibitory activity than natural sinomenine and other derivatives.

  本研究探讨了含有小型药物类氮杂环基团的盐酸缬草碱衍生物对肿瘤坏死因子-α（TNF-α）产生的抑制作用。发现几种具有氯苯基取代基的新型盐酸缬草碱衍生物展现出比天然盐酸缬草碱及其他衍生物更强的TNF-α抑制活性。
• METHOD FOR PRODUCING OPTICALLY ACTIVE AMINE COMPOUND
  申请人：Kanto Kagaku Kabushiki Kaisha

  公开号：US20130197234A1

  公开（公告）日：2013-08-01

  The present invention relates to methods for producing an optically active amine compound via a highly enantioselective hydrogenation reaction of an imine compound, wherein the imine compound is hydrogenated using a ruthenium metal complex having high catalytic activity and represented by Formula (1) RuXYAB  (1) such as RuBr 2 [(S,S)-xylskewphos][(S,S)-dpen].

  本发明涉及通过高度对映选择性的氢化反应制备光学活性胺化合物的方法，其中使用具有高催化活性的钌金属配合物对亚胺化合物进行氢化，该钌金属配合物由式（1）RuXYAB表示，例如RuBr2[(S,S)-xylskewphos][(S,S)-dpen]。
• TRANSITION METAL COMPLEXES FOR ENANTIOSELECTIVE CATALYSIS OF CARBON-CARBON, CARBON-HETEROATOM, AND CARBON-HYDROGEN BOND FORMING REACTIONS
  申请人：THE TEXAS A&M UNIVERSITY SYSTEM

  公开号：US20150165429A1

  公开（公告）日：2015-06-18

  In some embodiments, the present disclosure pertains to a compound, comprising a transition metal complex having the formula Φ-[M(x,y)-L 1 (w,v)-L 2 (t,u)-L 3 ] p+ An − m Z − p — m . In an embodiment of the present disclosure Φ may be A. In another embodiment Φ may be Δ. In some embodiments of the present disclosure, M is a transition metal. In a related embodiment, p is an integer corresponding to the oxidation state of M. In some embodiments of the present disclosure, each of x, y, w, v, t, and u independently comprise R. In other embodiments, each of x, y, w, v, t, and u independently comprise S. In an embodiment of the present disclosure, each of L 1 , L 2 , and L 3 independently is a ligand comprising a substituted diamine. In some embodiments, An″ comprises a lipophilic anion, where m is from 1 to 3, and where Z − comprises an optional second anion.

  在某些实施例中，本公开涉及一种化合物，包括具有公式Φ-[M（x，y）-L1（w，v）-L2（t，u）-L3]p+An−mZ−p—m的过渡金属配合物。在本公开的某种实施例中，Φ可以是A。在另一种实施例中，Φ可以是Δ。在本公开的某些实施例中，M是一种过渡金属。在相关实施例中，p是与M的氧化态相对应的整数。在本公开的某些实施例中，x，y，w，v，t和u中的每个都独立地包括R。在其他实施例中，x，y，w，v，t和u中的每个都独立地包括S。在本公开的某种实施例中，L1、L2和L3中的每个都独立地是包含取代二胺的配体。在某些实施例中，An″包括一个亲脂性阴离子，其中m从1到3，而Z−包括一个可选的第二个阴离子。
• PROCESS FOR THE STEREOSELECTIVE PREPARATION OF A PYRAZOLE CARBOXAMIDE
  申请人：Syngenta Participations AG

  公开号：US20140364622A1

  公开（公告）日：2014-12-11

  The present invention relates to a process for the enantioselective preparation of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid ((1S,4R)-9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide of formula Ib.

  本发明涉及一种对3-二氟甲基-1-甲基-1H-吡唑-4-羧酸((1S,4R)-9-二氯甲基-1,2,3,4-四氢-1,4-甲基-萘-5-基)-酰胺(Ib式)进行对映选择性制备的方法。