((1S,2S)-2-methyl-3-oxo-1-(p-tolyl)propyl)carbamic acid tert-butyl ester | 1207386-20-6

• 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: ((1S,2S)-2-methyl-3-oxo-1-(p-tolyl)propyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S,2S)-2-methyl-1-(4-methylphenyl)-3-oxopropyl]carbamate
• CAS: 1207386-20-6
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: UWCLLWITOMOCDI-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((1S,2S)-2-methyl-3-oxo-1-(p-tolyl)propyl)carbamic acid tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 indium 作用下， 以 水 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  A concise diastereoselective approach to enantioenriched substituted piperidines and their in vitro cytotoxicity evaluation

  摘要：

  A library of diversely stereo-oriented, highly substituted 2,6-cis piperidine derivatives were synthesized, and evaluated for their anticancer activity in cancer cells that included A549 (lung cancer, CCL-185), MCF7 (breast cancer (HTB-22), DU145 (prostate cancer (HTB-81), and HeLa (cervical cancer, CCL-2). One stereo-variant emerged as a promising candidate for further design based structure-activity studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.003
• 作为产物：
  描述：

  丙醛 、 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine 在 L-脯氨酸 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 ((1S,2S)-2-methyl-3-oxo-1-(p-tolyl)propyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  A concise diastereoselective approach to enantioenriched substituted piperidines and their in vitro cytotoxicity evaluation

  摘要：

  A library of diversely stereo-oriented, highly substituted 2,6-cis piperidine derivatives were synthesized, and evaluated for their anticancer activity in cancer cells that included A549 (lung cancer, CCL-185), MCF7 (breast cancer (HTB-22), DU145 (prostate cancer (HTB-81), and HeLa (cervical cancer, CCL-2). One stereo-variant emerged as a promising candidate for further design based structure-activity studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.003

文献信息

• 一种手性β-氨基醛类化合物的不对称合成方法
  申请人：浙江工业大学

  公开号：CN110845288B

  公开（公告）日：2022-07-19

  本发明公开了一种如式(I)所示的手性β‑氨基醛类化合物的不对称合成方法，所述的不对称合成是以式(Ⅱ)所示的亚胺和式(Ⅲ)所示的醛作为反应物，在有机溶剂中进行反应，其特征在于：所述的反应在手性催化剂和聚合物构建的超分子催化剂作用下进行；所述的手性催化剂选择下列之一：所述的聚合物选自PEG和/或PPG；本发明利用PPG/PEG与手性催化剂构建超分子催化剂用于手性β‑氨基醛类化合物的不对称合成，显著提高了产物收率。
• One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids
  作者：Luca Deiana、Gui-Ling Zhao、Pawel Dziedzic、Ramon Rios、Jan Vesely、Jesper Ekström、Armando Córdova

  DOI：10.1016/j.tetlet.2009.10.130

  日期：2010.1

  A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97–>99% ee.

  提出了对氨基甲酸酯和苯甲酸酯保护的β-氨基醛和β-氨基酸的高度对映选择性催化途径。未经修饰的醛与α-酰胺基砜之间的氨基酸催化的一锅不对称反应可得到相应的β-氨基酸，其dr含量高达95：5，ee高达97-> 99％。
• A concise diastereoselective approach to enantioenriched substituted piperidines and their in vitro cytotoxicity evaluation
  作者：Gullapalli Kumaraswamy、Rangaraju Satish Kumar、Bitla Sampath、Y. Poornachandra、C. Ganesh Kumar、Sahithya Phani Babu Vemulapalli、Jagadeesh Bharatam

  DOI：10.1016/j.bmcl.2014.08.003

  日期：2014.9

  A library of diversely stereo-oriented, highly substituted 2,6-cis piperidine derivatives were synthesized, and evaluated for their anticancer activity in cancer cells that included A549 (lung cancer, CCL-185), MCF7 (breast cancer (HTB-22), DU145 (prostate cancer (HTB-81), and HeLa (cervical cancer, CCL-2). One stereo-variant emerged as a promising candidate for further design based structure-activity studies. (C) 2014 Elsevier Ltd. All rights reserved.