(S)-2-[3'-(3,5-bis-trifluoromethyl)phenyl-thioureido]-3-phenyl propionic acid | 1042303-78-5

• 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-[3'-(3,5-bis-trifluoromethyl)phenyl-thioureido]-3-phenyl propionic acid
• 英文别名: (2S)-2-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]-3-phenylpropanoic acid
• CAS: 1042303-78-5
• 化学式: C₁₈H₁₄F₆N₂O₂S
• 分子量: 436.378
• InChiKey: PLACJHWXHVDDDB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  L-苯丙氨酸 、 3,5-双(三氟甲基)苯基异硫氰酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 生成 (S)-2-[3'-(3,5-bis-trifluoromethyl)phenyl-thioureido]-3-phenyl propionic acid
  参考文献：
  名称：

  高对映选择性迈克尔加成酮由吡咯烷基硫代咪唑和手性硫脲基酸的高效有机催化剂体系来催化nitrodienes †

  摘要：

  可利用的和可精细调节的有机催化体系有效地促进了酮对硝基二烯的高对映选择性迈克尔加成反应。 吡咯烷基-硫代咪唑 和手性 硫脲基酸。相应的加合物以良好的收率提供，具有高的非对映选择性（高达99：1）和优异的对映选择性（高达99％ee）。

  DOI：

  10.1039/c002197k
• 作为试剂：
  描述：

  4-溴巴豆酸乙酯 在 (S)-2-[3'-(3,5-bis-trifluoromethyl)phenyl-thioureido]-3-phenyl propionic acid 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 ethyl 2-((3S,4S,5R)-1-benzyl-4-nitro-5-phenylpyrrolidin-3-yl)acetate
  参考文献：
  名称：

  Organocatalytic asymmetric synthesis of trisubstituted pyrrolidines via a cascade reaction

  摘要：

  A new bifunctional thiourea II catalyzed methodology was developed for the synthesis of chiral trisubstituted pyrrolidines using 4-aminocrotonate 1a/1b and nitroolefins 2a-g as starting materials. Two different N-protected 4-aminocrotonates la and 1b were tested for the reaction with la giving the desired product 3a with a high diastereomeric ratio (>20:1) but with low enantioselectivity (ee up to 7%). N-Tosyl-4-aminocrotonate 1b, however, yielded the product with moderate dr (up to 68:32) but with high ee in the case of the major trans-trans-isomers 4a-g (ee from 92% to 98%) and modest enantiomeric excess for the minor trans-cis-isomers 4a'-g' (ee up to 57%). This methodology was also successfully applied when (E)-beta-methyl-trans-beta-nitrostyrene 2h was used as the starting nitroalkene to provide the product with dr 70/30 and with ee of 63% and 67%, respectively. The absolute configuration of both isomers was established using chiral derivatization with Mosher's and mandelic acids, with the relative stereochemistry being determined via NMR analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.021

文献信息

• A chiral thioureido acid as an effective additive for enantioselective organocatalytic Michael additions of nitroolefins
  作者：Dan-Qian Xu、Hua-Dong Yue、Shu-Ping Luo、Ai-Bao Xia、Shuai Zhang、Zhen-Yuan Xu

  DOI：10.1039/b804541k

  日期：——

  A novel and effective organocatalytic system consisting of pyrrolidinyl-thioimidazole and a chiral thioureido acid efficiently catalyzed the asymmetric Michael addition reactions of ketones to nitroolefins to afford the adducts with high diastereoselectivities (up to 99 : 1) and excellent enantioselectivities (up to 99% ee).

  由吡咯烷基-硫代咪唑和手性硫脲基酸组成的新型有效有机催化体系可有效催化酮与硝基烯烃的不对称迈克尔加成反应，从而提供具有高非对映选择性（高达99：1）和出色的对映选择性（高达99％ee）的加合物。 ）。
• The highly enantioselective Michael addition of ketones to nitrodienes catalyzed by the efficient organocatalyst system of pyrrolidinyl-thioimidazole and chiral thioureido acid
  作者：Zhao-Bo Li、Shu-Ping Luo、Yi Guo、Ai-Bao Xia、Dan-Qian Xu

  DOI：10.1039/c002197k

  日期：——

  The highly enantioselective Michael addition reaction of ketones to nitrodienes was promoted efficiently by the accessible and fine-tunable organocatalytic system of pyrrolidinyl-thioimidazole and chiral thioureido acid. The corresponding adducts were afforded in good yields with high diastereoselectivities (up to 99 : 1) and excellent enantioselectivities (up to 99% ee).

  可利用的和可精细调节的有机催化体系有效地促进了酮对硝基二烯的高对映选择性迈克尔加成反应。 吡咯烷基-硫代咪唑 和手性 硫脲基酸。相应的加合物以良好的收率提供，具有高的非对映选择性（高达99：1）和优异的对映选择性（高达99％ee）。