N,N'-[(R,R)-1,6-diphenylhexa-1,5-diyne-3,4-diyl]bis[N-(3,5-dimethylbenzyl)hydroxylamine] | 1040748-46-6

• 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,N'-[(R,R)-1,6-diphenylhexa-1,5-diyne-3,4-diyl]bis[N-(3,5-dimethylbenzyl)hydroxylamine]
• 英文别名: N-[(3,5-dimethylphenyl)methyl]-N-[(3R,4R)-4-[(3,5-dimethylphenyl)methyl-hydroxyamino]-1,6-diphenylhexa-1,5-diyn-3-yl]hydroxylamine
• CAS: 1040748-46-6
• 化学式: C₃₆H₃₆N₂O₂
• 分子量: 528.694
• InChiKey: IDOIVOUNVXNYMF-LQFQNGICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N'-(ethane-1,2-diylidene)bis[(3,5-dimethylphenyl)methanamine oxide] 、 苯乙炔 在 溴丁基-镁 、 Dimethylzinc 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 18.0h， 以14%的产率得到N,N'-[(R,S)-1,6-diphenylhexa-1,5-diyne-3,4-diyl]bis[N-(3,5-dimethylbenzyl)hydroxylamine]
  参考文献：
  名称：

  Catalytic asymmetric dialkynylation reaction of α-dinitrone by utilizing tartaric acid ester as a chiral auxiliary

  摘要：

  The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1-alkynes, to alpha-dinitrones derived from glyoxal and N-(4-isopropylbenzyl)hydroxylamine was investigated by utilizing dicyclohexyl (R,R)-tartrate as a chiral auxiliary. The addition reaction of methyl(2-phenylethynyl)zinc afforded the corresponding optically active C-2-symmetric (R,R)-bis(hydroxylamine) derivative with enantioselectivities of 90% and 81% ee by utilizing a stoichiometric and catalytic amount of the tartrate, respectively. Furthermore, the catalytic addition reaction of several alkynylzinc reagents also furnished the corresponding bis(hydroxylamine) with moderate to good enantioselectivities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.033

文献信息

• Catalytic asymmetric dialkynylation reaction of α-dinitrone by utilizing tartaric acid ester as a chiral auxiliary
  作者：Masakazu Serizawa、Shuhei Fujinami、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1016/j.tetasy.2008.03.033

  日期：2008.5

  The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1-alkynes, to alpha-dinitrones derived from glyoxal and N-(4-isopropylbenzyl)hydroxylamine was investigated by utilizing dicyclohexyl (R,R)-tartrate as a chiral auxiliary. The addition reaction of methyl(2-phenylethynyl)zinc afforded the corresponding optically active C-2-symmetric (R,R)-bis(hydroxylamine) derivative with enantioselectivities of 90% and 81% ee by utilizing a stoichiometric and catalytic amount of the tartrate, respectively. Furthermore, the catalytic addition reaction of several alkynylzinc reagents also furnished the corresponding bis(hydroxylamine) with moderate to good enantioselectivities. (C) 2008 Elsevier Ltd. All rights reserved.