2-(2-propenoyl)-naphtho[1,8-cd]isothiazole 1,1-dioxide | 474974-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-propenoyl)-naphtho[1,8-cd]isothiazole 1,1-dioxide
• 英文别名: 1-(2,2-Dioxo-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-3-yl)prop-2-en-1-one；1-(2,2-dioxo-2λ6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-3-yl)prop-2-en-1-one
• CAS: 474974-33-9
• 化学式: C₁₃H₉NO₃S
• 分子量: 259.285
• InChiKey: MZPOTDDASYWRMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tri-n-butylcrotyltin 、 碘乙烷 、 2-(2-propenoyl)-naphtho[1,8-cd]isothiazole 1,1-dioxide 在 三乙基硼 、 氧气 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 以30%的产率得到1-(1,1-Dioxo-1H-1λ⁶-naphtho[1,8-cd]isothiazol-2-yl)-3-methyl-2-propyl-pent-4-en-1-one
  参考文献：
  名称：

  Crotylations of α-Carbonyl Radicals with Crotylstannane

  摘要：

  [GRAPHICS]Electrophilic radicals undergo crotylation with crotylstannane with moderate to good efficiency. The reaction provides the syn isomer as the major product. The present methodology is complementary to Claisen protocols for the synthesis of gamma,delta-unsaturated carboxylic acid derivatives. Details of the new radical methodology are presented.

  DOI：

  10.1021/ol026510a
• 作为产物：
  描述：

  丙烯酰氯 、 1,8-萘磺内酰胺 在 正丁基锂 作用下， 生成 2-(2-propenoyl)-naphtho[1,8-cd]isothiazole 1,1-dioxide
  参考文献：
  名称：

  Crotylations of α-Carbonyl Radicals with Crotylstannane

  摘要：

  [GRAPHICS]Electrophilic radicals undergo crotylation with crotylstannane with moderate to good efficiency. The reaction provides the syn isomer as the major product. The present methodology is complementary to Claisen protocols for the synthesis of gamma,delta-unsaturated carboxylic acid derivatives. Details of the new radical methodology are presented.

  DOI：

  10.1021/ol026510a

文献信息

• Enantioselective Diels-Alder Reactions: Effect of the Achiral Template on Reactivity and Selectivity
  作者：Mukund Sibi、Jianxie Chen、Levi Stanley

  DOI：10.1055/s-2007-968014

  日期：2007.2

  Several achiral templates have been evaluated in chiral Lewis acid mediated enantioselective Diels-Alder reactions. Templates such as pyrrolidinones and pyrazolidinones that are capable of forming six-membered chelates with the Lewis acid exhibited the best reactivity and highest selectivity.

  已经在手性路易斯酸介导的对映选择性狄尔斯-阿尔德反应中评估了几种非手性模板。能够与路易斯酸形成六元螯合物的吡咯烷酮和吡唑烷酮等模板表现出最好的反应性和最高的选择性。
• Crotylations of α-Carbonyl Radicals with Crotylstannane
  作者：Mukund P. Sibi、Hideto Miyabe

  DOI：10.1021/ol026510a

  日期：2002.10.1

  [GRAPHICS]Electrophilic radicals undergo crotylation with crotylstannane with moderate to good efficiency. The reaction provides the syn isomer as the major product. The present methodology is complementary to Claisen protocols for the synthesis of gamma,delta-unsaturated carboxylic acid derivatives. Details of the new radical methodology are presented.