ethyl N-[(4-chlorophenyl)(tosyl)methyl]carbamate | 1190879-95-8

• 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-chlorophenyl)(tosyl)methyl]carbamate
• CAS: 1190879-95-8
• 化学式: C₁₇H₁₈ClNO₄S
• 分子量: 367.853
• InChiKey: RZEGXBUXTACUFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl N-[(4-chlorophenyl)(tosyl)methyl]carbamate 在 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 16.25h， 生成 ethyl (1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)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
• 作为产物：
  描述：

  sodium 4-methylbenzenesulfinate 在 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 ethyl N-[(4-chlorophenyl)(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。