benzyl N-<1-((p-methylphenyl)sulfonyl)ethyl>carbamate | 147169-13-9

• 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: benzyl N-<1-((p-methylphenyl)sulfonyl)ethyl>carbamate
• 英文别名: benzyl N-{1-[(4-methylphenyl)sulfonyl]ethyl}carbamate；benzyl N-[1-(4-methylphenyl)sulfonylethyl]carbamate
• CAS: 147169-13-9
• 化学式: C₁₇H₁₉NO₄S
• 分子量: 333.408
• InChiKey: BWWOIRRCADHIIS-UHFFFAOYSA-N

物化性质

• 沸点：
  540.2±50.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苄基马来酸酯 、 benzyl N-<1-((p-methylphenyl)sulfonyl)ethyl>carbamate 在 QD-4 cesium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.0h， 以64%的产率得到Dibenzyl 2-[1-(phenylmethoxycarbonylamino)ethyl]propanedioate
  参考文献：
  名称：

  Cinchona Alkaloid-Catalyzed Asymmetric Mannich Reactions

  摘要：

  羰酸酯保护的烷基亚胺的不稳定性大大阻碍了催化不对称Mannich反应的发展，该反应适用于合成光学活性的羰酸酯保护的手性烷基胺。已经开发出一种有机催化剂催化的高对映选择性Mannich反应，该反应从稳定的α-氨基磺酸盐中原位生成羰酸酯保护的亚胺。该反应提供了一种简洁而高度对映选择性的途径，将芳香族和脂肪族醛转化为光学活性的芳基和烷基β-氨基酸。

  公开号：

  US20080228000A1
• 作为产物：
  描述：

  氨基甲酸苄酯 、 乙醛 、 sodium 4-methylbenzenesulfinate 在 甲酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到benzyl N-<1-((p-methylphenyl)sulfonyl)ethyl>carbamate
  参考文献：
  名称：

  Pearson, William H.; Lindbeck, Aline C.; Kampf, Jeff W., Journal of the American Chemical Society, 1993, vol. 115, # 7, p. 2622 - 2633

  摘要：

  DOI：

文献信息

• An easy entry to optically active α-amino phosphonic acid derivatives using phase-transfer catalysis (PTC)
  作者：Francesco Fini、Gabriele Micheletti、Luca Bernardi、Daniel Pettersen、Mariafrancesca Fochi、Alfredo Ricci

  DOI：10.1039/b807027j

  日期：——

  The unprecedented use of phase-transfer catalysis (PTC) in an asymmetric hydrophosphonylation reaction allows the obtainment of a range of optically active α-amino phosphonic acid derivatives directly from α-amido sulfones.

  在不对称亲水磷腈反应中空前绝后地使用相转移催化（PTC），使得直接从α-酰胺砜获得一系列光学活性的α-氨基膦酸衍生物成为可能。
• Asymmetric Mannich Reactions with in Situ Generation of Carbamate-Protected Imines by an Organic Catalyst
  作者：Jun Song、Hui-Wen Shih、Li Deng

  DOI：10.1021/ol062837q

  日期：2007.2.1

  the synthesis of optically active carbamate-protected chiral alkyl amines. A highly enantioselective Mannich reaction with in situ generation of carbamate-protected imines from stable alpha-amido sulfones catalyzed by an organic catalyst was developed. This reaction provides a concise and highly enantioselective route converting aromatic and aliphatic aldehydes into optically active aryl and alkyl beta-amino

  氨基甲酸酯保护的烷基亚胺的不稳定性极大地阻碍了适于合成光学活性氨基甲酸酯保护的手性烷基胺的催化不对称曼尼希反应的发展。开发了高度对映选择性的曼尼希反应，其由有机催化剂催化的稳定α-酰胺基砜原位生成氨基甲酸酯保护的亚胺。该反应提供了简洁且高度对映选择性的途径，将芳族和脂族醛转化为光学活性的芳基和烷基β-氨基酸。[反应：请参见文字]。
• Phase-Transfer-Catalyzed Enantioselective Mannich Reaction of Malonates with α-Amido Sulfones
  作者：Francesco Fini、Luca Bernardi、Raquel P. Herrera、Daniel Pettersen、Alfredo Ricci、Valentina Sgarzani

  DOI：10.1002/adsc.200600250

  日期：2006.10

  The highly enantioselective reaction between in situ generated, Cbz-protected azomethines and malonates in the presence of 150 mol % of potassium carbonate (50 % w/w) and 1 mol % of quinine-derived quaternary ammonium bromides as phase-transfer organocatalysts has been developed. This study reports a novel approach for the asymmetric Mannich-type reaction and a wide range of azomethines, including

  在存在150 mol％碳酸钾（50％w / w）和1 mol％奎宁衍生的季铵溴化物作为相转移有机催化剂的情况下，原位生成的Cbz保护的偶氮甲磺酸和丙二酸酯之间存在高度对映选择性反应。发达。这项研究报告了一种用于不对称曼尼希型反应的新方法，本系统可耐受多种甲亚胺，包括衍生自可烯化醛的甲亚胺。以高达98％ee的高收率获得的加合物是光学纯的β-氨基酸的合适前体。
• Asymmetric Organocatalytic Monofluorovinylations
  作者：Christian Borch Jacobsen、Martin Nielsen、Dennis Worgull、Theo Zweifel、Esben Fisker、Karl Anker Jørgensen

  DOI：10.1021/ja110624k

  日期：2011.5.18

  The development of highly enantio- and c organocatalytic monofluorovinylations is presented. Based on the application of alpha-fluoro beta-keto-benzothiazolesulfones, the formal addition of a monofluorovinylic anion synthon to a range of acydic and cyclic enones, as well as imines, is shown. These procedures give selective access to both E- and Z-isomers of the monofluorovinylated products, which are isolated as the pure diastereoisomers in good to excellent yields with up to 99% ee. Furthermore, the application of this concept for the formation of highly enantioenriched bicylic compounds containing a monofluorovinyl moiety is also described. In addition, a mechanistic rationale for the observed E:Z-selectivities is presented.
• N-Carbamate α-aminoalkyl-p-tolylsulfones—convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates
  作者：Roman Błaszczyk、Anna Gajda、Stefan Zawadzki、Ewelina Czubacka、Tadeusz Gajda

  DOI：10.1016/j.tet.2010.10.072

  日期：2010.12

  An efficient one-pot synthesis of secondary N-carbamate protected syn-beta-amino-alpha-nitroalkanephosphonates using diethyl nitromethanephosphonate and N-Boc or N-Cbz imines, generated in Situ from stable N-Boc or N-Cbz alpha-aminoalkyl-p-tolylsulfones has been developed under PTC conditions. A model enantioselective version of this reaction is also described. Enantioselectivity up to 67% ee is achieved using a chiral thiourea catalyst derived from a cinchona alkaloid. Completely stereoselective conversion of the title compounds into partially N-carbamate protected syn-1,2-diaminoalkanephosphonates has also been elaborated. (C) 2010 Elsevier Ltd. All rights reserved.