ethyl (S)-2-tosylamino-4-pentynoate | 440677-36-1

• 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: ethyl (S)-2-tosylamino-4-pentynoate
• 英文别名: ethyl (2S)-2-[(4-methylphenyl)sulfonylamino]pent-4-ynoate
• CAS: 440677-36-1
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: QAKFFHZMFFXDRX-ZDUSSCGKSA-N

物化性质

• 沸点：
  441.3±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (S)-2-tosylamino-4-pentynoate 在 tetrakis(acetonitrile)copper(I) perchlorate 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (S)-1-tosyl-4,5-didehydroproline ethyl ester
  参考文献：
  名称：

  One-pot synthesis of chiral dehydroproline esters: [3+2]-type cycloaddition reaction of allenylstannane and α-imino ester

  摘要：

  An enantioselective [3+2]-type cycloaddition of allenylstannane and alpha-imino ester was developed. Synthetic utility of the 4stannyldehydroproline ester intermediate was demonstrated: iodine oxidation and Stille coupling reaction of the intermediate afforded optically active 4-iodo- and 4-aryldehydroproline esters in good yields and in high ees, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.018
• 作为产物：
  描述：

  1,2-丙二烯三正丁基锡 、 ethyl (N-tosylimino)acetate 在 tetrakis(acetonitrile)copper(I) perchlorate 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 ethyl (R)-2-tosylamino-4-pentynoate 、 ethyl (S)-2-tosylamino-4-pentynoate
  参考文献：
  名称：

  One-pot synthesis of chiral dehydroproline esters: [3+2]-type cycloaddition reaction of allenylstannane and α-imino ester

  摘要：

  An enantioselective [3+2]-type cycloaddition of allenylstannane and alpha-imino ester was developed. Synthetic utility of the 4stannyldehydroproline ester intermediate was demonstrated: iodine oxidation and Stille coupling reaction of the intermediate afforded optically active 4-iodo- and 4-aryldehydroproline esters in good yields and in high ees, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.018

文献信息

• Catalytic, Enantioselective Propargyl- and Allenylation Reactions of α-Imino Ester
  作者：Hirotaka Kagoshima、Tetsumaru Uzawa、Takahiko Akiyama

  DOI：10.1246/cl.2002.298

  日期：2002.3

  Catalytic, enantioselective propargyl- and allenylation reactions of α-imino ester have been achieved by means of the [Cu(MeCN)4]ClO4/(R)-tol-BINAP catalyst to afford the corresponding propargyl- and allenyl-substituted α-amino acid derivatives, respectively, in good yields with good enantiomeric excesses.

  已经通过 [Cu(MeCN)4]ClO4/(R)-tol-BINAP 催化剂实现了 α-亚氨基酯的催化、对映选择性炔丙基和烯丙基化反应，得到相应的炔丙基和烯丙基取代的 α-氨基酸衍生物，分别以良好的收率和良好的对映体过量。
• Enantioselective three-component synthesis of 4-arylated dehydroprolines: [3+2] annulation of allenylstannane and α-imino ester
  作者：Kohei Fuchibe、Rina Hatemata、Takahiko Akiyama

  DOI：10.1016/j.tetlet.2005.09.194

  日期：2005.12

  An enantioselective [3+2] annulation reaction of allenylstannane and alpha-imino ester was developed. Stille coupling of the resulting 4-stannyl dehydroproline gave optically active 4-arylated dehydroprolines in good yields. (c) 2005 Elsevier Ltd. All rights reserved.