N-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide | 137845-39-7

• 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: N-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide
• 英文别名: (e)-N-(3,4-dimethoxybenzylidene)-4-methylbenzenesulfonamide；(NE)-N-[(3,4-dimethoxyphenyl)methylidene]-4-methylbenzenesulfonamide
• CAS: 137845-39-7
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: PCDBEXWNGILFIE-GZTJUZNOSA-N

物化性质

• 沸点：
  472.9±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 N-[(1S)-1-(3,4-dimethoxyphenyl)-3-oxopropyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  一种简明和对映选择性的方法，可合成（-）-lasubine I

  摘要：

  （-）-lasubine I（1）的有效，对映选择性全合成已从容易获得的起始原料中以8.8％的总收率实现。该方法的重要特征包括通过两个连续的高度立体选择性的Roush烯丙基硼酸酯形成立体异构中心，以及使用S N 2环化和闭环复分解反应来构建喹喔啉骨架。

  DOI：

  10.1016/j.tetlet.2006.08.137
• 作为产物：
  描述：

  N-[(3,4-dimethoxyphenyl)-(4-methylphenyl)sulfonylmethyl]-4-methylbenzenesulfonamide 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到N-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Practical and General Entry toN‐Tosyl Aryl Aldimines Promoted by Sulfamic Acid in Water and Alcohol

  摘要：

  A practical, indirect procedure composed of a three-component condensation using aromatic aldehydes, p-tosylamide, and sodium p-toluenesulfinate in the presence of sulfamic acid in tap water-alcohol solvents to afford amidosulfones, and the subsequent water two-phase basic elimination of the amidosulfones to N-tosyl arylimines, was developed. The process has little environmental impact, easy workup, mild reaction conditions, and good yields and is amenable to large-scale preparations.

  DOI：

  10.1080/00397910601131387

文献信息

• Catalytic Enantioselective Approach to the Stereodivergent Synthesis of (+)-Lasubines I and II
  作者：Olga García Mancheño、Ramón Gómez Arrayás、Javier Adrio、Juan C. Carretero

  DOI：10.1021/jo702076j

  日期：2007.12.1

  A concise and efficient approach to the stereodivergent synthesis of (+)-lasubines I and II is described. The key common intermediate is a chiral N-sulfonyl 2,3-dihydropyridone obtained by a novel Cu-catalyzed asymmetric formal aza-Diels−Alder reaction between N-tosyl aldimines and Danishefsky's diene.

  描述了一种简洁高效的立体异构合成（+）-异戊二烯I和II的方法。关键的常见中间体是手性N-磺酰基2,3-二氢吡啶酮，它是通过N-甲苯磺酰基亚胺与Danishefsky's二烯之间新型的Cu催化的不对称形式的Aza -Diels-Alder形式反应而获得的。
• Highly diastereoselective Mannich-type reaction of titanium enolate derived from 2′-hydroxypropiophenone
  作者：Guisheng Deng、Honghua Mo、Jing Luo、Jingyuan Zou

  DOI：10.1139/v2012-027

  日期：2012.6

  N-tosylimines. Noteworthy is the observation that the influence of a second Lewis acid on the Mannich-type reaction based on the titanium enolate is opposite to that obtained from other titanium enolates reported. A reasonable mechanism has been proposed to explain the high anti diastereoselectivity and the effect of a second Lewis acid on yield.

  从 2'-羟基苯丙酮衍生的钛烯醇化物与 N-甲苯磺酰亚胺的曼尼希型加成提供了相应的 β-氨基酮，产率良好至极好 (60%–90%)，并且具有 >99: <1 的抗非对映选择性。已经开发了一种基于钛烯醇化物合成抗 β-氨基酮作为主要异构体的模型。高抗选择性与 N-甲苯磺酰亚胺苯环上的给电子和吸电子基团无关。值得注意的是，第二个路易斯酸对基于钛烯醇化物的曼尼希型反应的影响与报道的其他钛烯醇化物相反。已经提出了一种合理的机制来解释高抗非对映选择性和第二种路易斯酸对产率的影响。
• Asymmetric synthesis of β-amino acids through application of chiral sulfoxide
  作者：A.V. Sivakumar、G.S. Babu、Sujata V. Bhat

  DOI：10.1016/s0957-4166(01)00185-9

  日期：2001.5

  This paper describes asymmetric synthesis of β-aminophenylpropionic acid through application of a homochiral sulfoxide auxiliary. High kinetically controlled (3R,2S,RS)-diastereoselectivity (−60°C) is achieved during addition of the lithium enolate of tert-butyl (+)-(R)-p-toluenesulfinylacetate to substituted N-(benzylidene)toluene-4-sulfonamides 2a–2d. The reductive cleavage of adduct 3a with sodium

  本文描述了通过使用手性亚砜辅助剂不对称合成β-氨基苯基丙酸。在将叔丁基（+）-（R）-对甲苯亚磺酰基乙酸乙酸酯的烯醇锂添加到取代的N-（亚苄基）中期间，实现了高动力学控制的（3 R，2 S，R S）-非对映选择性（−60°C））甲苯-4-磺酰胺2a - 2d。用汞齐钠对加合物3a的还原性裂解生成3-（甲苯-4-磺酰胺基）-3-苯基丙酸叔丁酯5a进行酯水解，然后用液氨中的钠脱甲苯磺酸，以良好的收率和91％ee高的收率得到（S）-β-氨基苯基丙酸
• Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I
  作者：Sabrina Castellano、Hannah D. G. Fiji、Sape S. Kinderman、Masaru Watanabe、Pablo de Leon、Fuyuhiko Tamanoi、Ohyun Kwon

  DOI：10.1021/ja070274n

  日期：2007.5.1

  Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics.
• Love Brian E., Raje Prasad S., J. Org. Chem, 59 (1994) N 11, S 3219-3222
  作者：Love Brian E., Raje Prasad S.

  DOI：——

  日期：——