ethyl N-[(4-methylphenyl)(tosyl)methyl]carbamate | 3696-53-5

• 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: ethyl N-[(4-methylphenyl)(tosyl)methyl]carbamate
• 英文别名: ethyl N-[(4-methylphenyl)-(4-methylphenyl)sulfonylmethyl]carbamate
• CAS: 3696-53-5
• 化学式: C₁₈H₂₁NO₄S
• 分子量: 347.435
• InChiKey: DHZOYYSNWCDHPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  ethyl N-[(4-methylphenyl)(tosyl)methyl]carbamate 在 sodium hydride 、 potassium penicillin V 、 肼 作用下， 以 水 、 乙腈 为溶剂， 反应 36.5h， 生成 hydrazone of 4-[1-(4-methylphenyl)-3-oxo-but-1-yl]semicarbazide
  参考文献：
  名称：

  新型14元环双-半咔唑的合成

  摘要：

  开发了一种有效的立体选择性合成新型14元环状双-半-氨基脲的方法，该方法基于3-（3-氧代丁基）-氨基脲的carb的酸催化环化反应。根据四步策略制备起始氨基脲，该策略涉及乙酰丙酮的烯醇钠与N-（α-甲苯磺酰基苄基）氨基甲酸酯的酰胺烷基化，然后进行碱促进的逆克莱森反应和处理所得的N-（3-氧代丁基）氨基甲酸酯与肼。

  DOI：

  10.1016/j.tetlet.2014.08.016
• 作为产物：
  描述：

  sodium 4-methylbenzenesulfinate 在 盐酸 作用下， 以 水 为溶剂， 反应 1.83h， 生成 ethyl N-[(4-methylphenyl)(tosyl)methyl]carbamate
  参考文献：
  名称：

  Different modes of acid-catalyzed cyclization of 4-(γ-oxoalkyl)semicarbazide hydrazones: 7-membered versus 14-membered cyclic semicarbazones formation

  摘要：

  Acid-catalyzed cyclization of 4-(gamma-oxoalkyl)semicarbazide hydrazones has been studied. 7-Membered cyclic semicarbazones, 2,4,5,6-tetrahydro-3H-1,2,4-triazepin-3-ones, were obtained from the gamma-phenyl-substituted semicarbazides, while the cyclization of the gamma-methyl-substituted semicarbazides involved two molecules of the starting material to result in 14-membered cyclic bis-semicarbazones, 1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones. The 4-(gamma-oxoalkyl)semicarbazide hydrazones were prepared according to a four-step synthesis based on amidoallcylation of the sodium enolates of 1,3-diketones with ethyl N-(1-tosylallc-1-yl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained ethyl N-(gamma-oxoalkyl)carbamates with hydrazine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.079

文献信息

• Highly Enantioselective Monofluoromethylation of C2-Arylindoles Using FBSM under Chiral Phase-Transfer Catalysis
  作者：Kohei Matsuzaki、Tatsuya Furukawa、Etsuko Tokunaga、Takashi Matsumoto、Motoo Shiro、Norio Shibata

  DOI：10.1021/ol4013102

  日期：2013.7.5

  The highly enantioselective addition of 1-fluoro-1,1-bis(phenylsulfonyl)methane (FBSM) to vinylogous imines generated in situ from 2-aryl-3-(1-arylsulfonylmethyl)indoles was achieved using chiral ammonium salts derived from cinchona alkaloids. One-pot conversion from 2-arylindoles with FBSM was also adaptable under the same reaction conditions. The key for this transformation is the effective use of

  使用衍生自金鸡纳生物碱的手性铵盐可将1-氟-1,1-双（苯磺酰基）甲烷（FBSM）高度对映选择性地添加到由2-芳基-3-（1-芳基磺酰基甲基）吲哚原位生成的乙烯基亚胺中。 。在相同的反应条件下，2-芳基吲哚与FBSM的一锅转化也适用。该转化的关键是芳基磺酰基的有效利用。
• InBr₃: A Versatile Catalyst for the Different Types of Friedel−Crafts Reactions
  作者：Ponnaboina Thirupathi、Sung Soo Kim

  DOI：10.1021/jo9014613

  日期：2009.10.16

  Mild and efficient InBr3-catalyzed Friedel−Crafts alkylation of heteroaromatic or electron-rich aromatic compounds with α-amido sulfones at room temperature in CH2Cl2 has been developed. The products undergo further Friedel−Crafts alkylation with heteroaromatic or electron-rich aromatic compounds leading to unsymmetrical or bis-symmetrical triaryl methanes in good yield. α-Amido sulfones are employed

  在室温下，在CH 2 Cl 2中，已开发出温和有效的InBr 3催化的杂芳族或富电子芳族化合物与α-酰胺基砜的Friedel-Crafts烷基化反应。产物进一步与杂芳族或富电子芳族化合物进行弗里德-克拉夫特烷基化反应，从而以高收率得到不对称或双对称的三芳基甲烷。α-酰胺基砜被用于合成不对称和双对称的三芳基甲烷。使用温和的反应条件，低催化负荷和高收率是本方法的优点。
• 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.
• Olijnsma,T. et al., Recueil des Travaux Chimiques des Pays-Bas, 1967, vol. 86, # 12, p. 1281 - 1287
  作者：Olijnsma,T. et al.

  DOI：——

  日期：——
• Engberts,J.B.F.N.; Strating,J., Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 942 - 950
  作者：Engberts,J.B.F.N.、Strating,J.

  DOI：——

  日期：——