(S)-2-isothiocyanato-3,3,N-trimethylbutyramide | 860994-90-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-isothiocyanato-3,3,N-trimethylbutyramide
• 英文别名: (S)-2-isothiocyanato-N,3,3-trimethylbutanamide；(2S)-2-isothiocyanato-N,3,3-trimethylbutanamide
• CAS: 860994-90-7
• 化学式: C₈H₁₄N₂OS
• 分子量: 186.278
• InChiKey: HDJZNLRFKVVRMR-ZCFIWIBFSA-N

物化性质

• 沸点：
  329.8±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-isothiocyanato-3,3,N-trimethylbutyramide 、 (R,R)-N,N-diethylcyclohexane-1,2-diamine 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到(R,R)-2-[3-(2-diethylaminocyclohexyl)thioureido]-3,3,N-trimethylbutyramide
  参考文献：
  名称：

  Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones

  摘要：

  The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a cooperative mechanism involving electrophile activation by thiourea and nucleophile activation by the amine.

  DOI：

  10.1021/ja052511x
• 作为产物：
  描述：

  N-Boc-L-叔亮氨酸 在 盐酸 、 碳酸氢钠 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 14.67h， 生成 (S)-2-isothiocyanato-3,3,N-trimethylbutyramide
  参考文献：
  名称：

  Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones

  摘要：

  The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a cooperative mechanism involving electrophile activation by thiourea and nucleophile activation by the amine.

  DOI：

  10.1021/ja052511x

文献信息

• Chiral thiourea compounds and process for enantioselective reduction of ketones
  申请人：Li Derun

  公开号：US20090253919A1

  公开（公告）日：2009-10-08

  Chiral thioureas are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols. A prochiral ketone may be reduced to an optically active alcohol in the presence of a substantially sub-stoichiometric amount of chiral thiourea. The asymmetric thiourea compound of the present invention may be produced according to a production method described herein.

  手性硫脲是对丙酮进行硼氢化还原生成光学活性醇的有效催化剂。在存在明显亚化学计量量手性硫脲的情况下，可以将一个丙酮还原为光学活性醇。本发明的不对称硫脲化合物可以根据本文描述的生产方法制备。
• Stereoselective nucleophilic addition to imines catalyzed by chiral bifunctional thiourea organocatalysts
  作者：Alessandra Puglisi、Maurizio Benaglia、Rita Annunziata、Davide Rossi

  DOI：10.1016/j.tetasy.2008.09.030

  日期：2008.10

  such bifunctional chiral molecules, either neutral or protonated species, was investigated in the addition of acetylacetone to β-nitrostyrene as a model reaction. Using the best conditions, high yields and enantioselectivities of up to 85% were obtained. The same metal free catalysts were then employed in the addition of activated nucleophiles to imines: in the reaction of 1,3-diketones with N-CBz imines

  通过（S）-t-亮氨酸衍生物与（1 R，2 R）-反式结合获得的新手性双功能有机催化剂的合成开发了-1，2-二氨基-环己烷。已经成功地合成了几种化合物，它们代表通过手性主链连接的含有硫脲基和叔氨基的一类有机催化剂。在模型反应中，向β-硝基苯乙烯中添加了乙酰丙酮，研究了这种中性或质子化双功能手性分子的催化行为。在最佳条件下，可获得高达85％的高收率和对映选择性。然后将相同的不含金属的催化剂用于向亚胺中添加活化的亲核试剂：在1,3-二酮与N -CBz亚胺的反应中，分离出的产物的收率高达61％ee，而与丙二酸二乙酯的反应则被分离出来。对映选择性高达71％。
• Enantioselective, Organocatalytic Reduction of Ketones using Bifunctional Thiourea-Amine Catalysts
  作者：De Run Li、Anyu He、J. R. Falck

  DOI：10.1021/ol100365c

  日期：2010.4.16

  Prochiral ketones are reduced to enantioenriched, secondary alcohols using catecholborane and a family of air-stable, bifunctional thiourea amine organocatalysts. Asymmetric induction is proposed to arise from the in situ complexation between the borane and chiral thiourea amine organocatalyst resulting in a stereochemically biased boronate amine complex. The hydride in the complex is endowed with enhanced nucleophilicity while the thiourea concomitantly embraces and activates the carbonyl.
• US8334405B2
  申请人：——

  公开号：US8334405B2

  公开（公告）日：2012-12-18
• Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones
  作者：Douglas E. Fuerst、Eric N. Jacobsen

  DOI：10.1021/ja052511x

  日期：2005.6.1

  The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a cooperative mechanism involving electrophile activation by thiourea and nucleophile activation by the amine.