2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide | 205578-94-5

• 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: 2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide
• 英文别名: 2-chloro-N-methyl-N-(6-phenylcyclohexen-1-yl)acetamide
• CAS: 205578-94-5
• 化学式: C₁₅H₁₈ClNO
• 分子量: 263.767
• InChiKey: KZAPMCFLMCGQHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide 在 偶氮二异丁腈 、 氘代三正丁基锡 作用下， 以 甲苯 为溶剂， 以14%的产率得到
  参考文献：
  名称：

  5-endo-trig Radical Cyclization of 2-Chloro- and 2,2-Bis(phenylthio)-N-methyl- N-(6-phenylcyclohex-1-en-1-yl)-acetamides

  摘要：

  Treatment of 2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)-acetamide (4a) with Bu3SnH in the presence of AIBN gave a 2.5:1 mixture of cis- and trans-fused N-methyl-7-phenyloctahydroindol-2-ones (5a and 5b) (13% combined yield), N-methyl-N-(2-phenylcyclohex-1-en-1-yl)acetamide (6) (19%), N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide (7) (13%), and N-(cyclohex-1-en-1-yl) -N-methyl-2-phenylacetamide (8) (4%). Similar treatment of the 2,2-bis(phenylthio)acetamide (4b) gave a 1:1 mixture of 5a and 5b (61% combined yield) along with 6 (24%) and 7 (trace). Possible mechanisms for the formation of the products (6)-(8) are also discussed.

  DOI：

  10.3987/com-96-7629
• 作为产物：
  描述：

  2-苯基环己酮 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.17h， 生成 2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide
  参考文献：
  名称：

  5-endo-trig Radical Cyclization of 2-Chloro- and 2,2-Bis(phenylthio)-N-methyl- N-(6-phenylcyclohex-1-en-1-yl)-acetamides

  摘要：

  Treatment of 2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)-acetamide (4a) with Bu3SnH in the presence of AIBN gave a 2.5:1 mixture of cis- and trans-fused N-methyl-7-phenyloctahydroindol-2-ones (5a and 5b) (13% combined yield), N-methyl-N-(2-phenylcyclohex-1-en-1-yl)acetamide (6) (19%), N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide (7) (13%), and N-(cyclohex-1-en-1-yl) -N-methyl-2-phenylacetamide (8) (4%). Similar treatment of the 2,2-bis(phenylthio)acetamide (4b) gave a 1:1 mixture of 5a and 5b (61% combined yield) along with 6 (24%) and 7 (trace). Possible mechanisms for the formation of the products (6)-(8) are also discussed.

  DOI：

  10.3987/com-96-7629

文献信息

• 5-endo-trig Radical Cyclization of 2-Chloro- and 2,2-Bis(phenylthio)-N-methyl- N-(6-phenylcyclohex-1-en-1-yl)-acetamides
  作者：Masazumi Ikeda、Shinji Ohtani、Michiyo Okada、Emi Minakuchi、Tatsunori Sato、Hiroyuki Ishibashi

  DOI：10.3987/com-96-7629

  日期：——

  Treatment of 2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)-acetamide (4a) with Bu3SnH in the presence of AIBN gave a 2.5:1 mixture of cis- and trans-fused N-methyl-7-phenyloctahydroindol-2-ones (5a and 5b) (13% combined yield), N-methyl-N-(2-phenylcyclohex-1-en-1-yl)acetamide (6) (19%), N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide (7) (13%), and N-(cyclohex-1-en-1-yl) -N-methyl-2-phenylacetamide (8) (4%). Similar treatment of the 2,2-bis(phenylthio)acetamide (4b) gave a 1:1 mixture of 5a and 5b (61% combined yield) along with 6 (24%) and 7 (trace). Possible mechanisms for the formation of the products (6)-(8) are also discussed.