(S)-(-)-N-[1-(p-bromophenyl)ethylidene]-tert-butanesulfinamide

• 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: (S)-(-)-N-[1-(p-bromophenyl)ethylidene]-tert-butanesulfinamide
• 英文别名: (S,E)-N-(1-(4-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide；(S)-N-[1-(4-bromophenyl)ethylidene]-2-methylpropane-2-sulfinamide
• 化学式: C₁₂H₁₆BrNOS
• 分子量: 302.235
• InChiKey: UGAMXWQQSPEBGU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O,O'-diethyl thiophosphonate 、 (S)-(-)-N-[1-(p-bromophenyl)ethylidene]-tert-butanesulfinamide 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以99%的产率得到diethyl (S(S),R(C))-(+)-[1-(4-bromophenyl)-1-(tert-butylsulfinylamino)ethyl]thiophosphonate
  参考文献：
  名称：

  （1-氨基烷基）硫代膦酸二乙酯的多功能和高立体选择性合成

  摘要：

  通过在温和条件下将二乙基硫代膦酸酯亲核加成到N-（叔丁基亚磺酰基）亚胺上，以高收率和优异的对映选择性合成了一系列手性二乙基（1-氨基烷基）硫代膦酸酯。没有证据表明该反应受底物的电子或空间效应影响。 亲核加成物-硫代膦酸酯-亚胺-亚磺酰胺-磺酰胺

  DOI：

  10.1055/s-0029-1217054
• 作为产物：
  描述：

  4-溴苯乙酮 、 S-叔丁基亚磺酰胺 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以89%的产率得到(S)-(-)-N-[1-(p-bromophenyl)ethylidene]-tert-butanesulfinamide
  参考文献：
  名称：

  含两个立体原子的α-氨基次膦酸酯的简明首次合成，可生成光学纯的α-氨基-H-次膦酸。

  摘要：

  DOI：

  10.1002/chem.200800690

文献信息

• Asymmetric Synthesis of Homoallylic Amines Bearing Adjacent Stereogenic Centers by Addition of Substituted Allylic Zinc Reagents to N-<i>tert</i>-Butanesulfinylimines
  作者：Leleti Rajender Reddy、Bin Hu、Mahavir Prashad、Kapa Prasad

  DOI：10.1021/ol800998u

  日期：2008.7.17

  diastereoselective addition of substituted racemic allylic zinc reagents to chiral N- tert-butanesulfinylimines resulting in the formation of homoallylic amines is reported. This method is quite general and also efficient for the preparation of enantiomerically pure homoallylic amines bearing quaternary centers and also adjacent quaternary centers.

  据报道，向手性N-叔丁烷亚磺酰亚胺中高度非对映选择性地添加了取代的外消旋烯丙基锌试剂，导致形成了均烯丙基胺。该方法是非常通用的，并且对于制备带有季中心以及相邻的季中心的对映体纯的均烯丙基胺也是有效的。
• Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: dual stereocontrol with nearly perfect diastereoselectivity
  作者：Yi-Shuang Zhao、Qiang Liu、Ping Tian、Jing-Chao Tao、Guo-Qiang Lin

  DOI：10.1039/c5ob00322a

  日期：——

  Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of a chiral auxiliary and a chiral copper complex, has played an important role in achieving the nearly perfect diastereoselectivities (all dr > 99 : 1), especially for ketimine substrates.

  已经描述了铜催化的手性N-叔-丁烷亚磺酰基亚胺的不对称烯丙基化。通过手性助剂和手性铜配合物的结合，双重立体控制在实现近乎完美的非对映选择性（所有dr> 99：1）方面起着重要作用，尤其是对于酮亚胺底物。
• N-BIPHENYLMETHYLBENZIMIDAZOLE MODULATORS OF PPARG
  申请人：RIPKA Amy S.

  公开号：US20150141464A1

  公开（公告）日：2015-05-21

  The invention provides molecular entities that bind with high affinity to PPARG (PPARγ), inhibit cdk5 -mediated phosphorylation of PPARG, but do not exert an agonistic effect on PPARG. Compounds of the invention can be used for treatment of conditions in patients wherein PPARG plays a role, such as diabetes or obesity. Methods of preparation of the compounds, bioassay methods for evaluating compounds of the invention as non-agonistic PPARG binding compounds, and pharmaceutical compositions are also provided.

  本发明提供了与PPARG（PPARγ）高亲和力结合，抑制cdk5介导的PPARG磷酸化，但不对PPARG产生激动作用的分子实体。本发明的化合物可用于治疗PPARG在糖尿病或肥胖症患者中发挥作用的情况。本发明还提供了制备该化合物的方法，评估该化合物作为非激动性PPARG结合化合物的生物测定方法以及制药组合物。
• N-BENZYLBENZIMIDAZOLE MODULATORS OF PPARG
  申请人：Kamenecka Theodore Mark

  公开号：US20140249196A1

  公开（公告）日：2014-09-04

  The invention provides molecular entities that bind with high affinity to PPARG (PPARγ), inhibit cdk5-mediated phosphorylation of PPARG, but do not exert an agonistic effect on PPARG. Compounds of the invention can be used for treatment of conditions in patients wherein PPARG plays a role, such as diabetes or obesity. Methods of preparation of the compounds, bioassay methods for evaluating compounds of the invention as non-agonistic PPARG binding compounds, and pharmaceutical compositions are also provided.

  本发明提供了与PPARG（PPARγ）高亲和力结合、抑制cdk5介导的PPARG磷酸化，但不对PPARG产生激动作用的分子实体。本发明的化合物可用于治疗PPARG在糖尿病或肥胖等病患中发挥作用的情况。本发明还提供了化合物的制备方法、评估本发明的化合物作为非激动性PPARG结合化合物的生物测定方法和制药组合物。
• Zinc-Mediated Asymmetric Additions of Dialkylphosphine Oxides to α,β-Unsaturated Ketones and <i>N</i>-Sulfinylimines
  作者：Depeng Zhao、Lijuan Mao、Dongxu Yang、Rui Wang

  DOI：10.1021/jo1014917

  日期：2010.10.15

  A catalyst was synthesized on the basis of Trost's dinuclear catalyst characterized by working well without pyridine in the present phospha-Michael reaction Nevertheless, the presence of pyridine is still advantageous in the present system The substrate scope was successfully extended to enones employing diallyl phosphine oxide as a nucleophile Excellent yields and enantioselectivities (up to >99% ee) wine achieved for a wide scope of enones employing the catalyst under mild conditions The detailed reaction mechanism is also discussed hetein Finally. the unprecedented asymmetric additions of dialkylphosphine oxides to N-sulfinylumines were achieved by using Et2Zn as a base