1-(4-Benzyloxymethoxy-6-chloro-cyclohex-1-enyl)-pyrrolidine | 160410-21-9

• 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: 1-(4-Benzyloxymethoxy-6-chloro-cyclohex-1-enyl)-pyrrolidine
• 英文别名: 1-[6-Chloro-4-(phenylmethoxymethoxy)cyclohexen-1-yl]pyrrolidine
• CAS: 160410-21-9
• 化学式: C₁₈H₂₄ClNO₂
• 分子量: 321.847
• InChiKey: CNZYCXZMJVCSMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-Benzyloxymethoxy-6-chloro-cyclohex-1-enyl)-pyrrolidine 、 螺[2.4]庚-4,6-二烯 在 sodium hydroxide 、 silver tetrafluoroborate 作用下， 生成 、
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals and Oxidative Elimination of Alicyclic Iodides

  摘要：

  The azaallyl cation-mediated [4 + 3] cycloaddition with spiro[2.4]hepta-4,6-diene by the procedure of Schmid provides the tricyclic cycloadducts of general type 3. The keto bridge of the cycloadducts 17c, 21, and 22 has been cleaved by PhI(OAc)(2)-I-2 (Suarez cleavage), which involves P-fragmentation of an alkoxy radical, to furnish iodo lactones 19, 32, and 30a,b, respectively. Subsequent oxidation of these alkyl iodides has been investigated to develop a new synthetic route for bridgehead olefins (i.e., 33) of medium-sized carbocycles.

  DOI：

  10.1021/jo00102a019
• 作为产物：
  描述：

  4-甲氧基环己-3-烯-1-醇 在 N-氯代丁二酰亚胺 、 sodium acetate 、 magnesium sulfate 作用下， 以 四氢呋喃 、 环己烷 、 水 为溶剂， 反应 2.0h， 生成 1-(4-Benzyloxymethoxy-6-chloro-cyclohex-1-enyl)-pyrrolidine
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals and Oxidative Elimination of Alicyclic Iodides

  摘要：

  The azaallyl cation-mediated [4 + 3] cycloaddition with spiro[2.4]hepta-4,6-diene by the procedure of Schmid provides the tricyclic cycloadducts of general type 3. The keto bridge of the cycloadducts 17c, 21, and 22 has been cleaved by PhI(OAc)(2)-I-2 (Suarez cleavage), which involves P-fragmentation of an alkoxy radical, to furnish iodo lactones 19, 32, and 30a,b, respectively. Subsequent oxidation of these alkyl iodides has been investigated to develop a new synthetic route for bridgehead olefins (i.e., 33) of medium-sized carbocycles.

  DOI：

  10.1021/jo00102a019

文献信息

• Fragmentation of Alkoxy Radicals and Oxidative Elimination of Alicyclic Iodides
  作者：Jinhwa Lee、Jonghoon Oh、Shu-juan Jin、Jong-Ryoo Choi、Jerry L. Atwood、Jin Kun Cha

  DOI：10.1021/jo00102a019

  日期：1994.11

  The azaallyl cation-mediated [4 + 3] cycloaddition with spiro[2.4]hepta-4,6-diene by the procedure of Schmid provides the tricyclic cycloadducts of general type 3. The keto bridge of the cycloadducts 17c, 21, and 22 has been cleaved by PhI(OAc)(2)-I-2 (Suarez cleavage), which involves P-fragmentation of an alkoxy radical, to furnish iodo lactones 19, 32, and 30a,b, respectively. Subsequent oxidation of these alkyl iodides has been investigated to develop a new synthetic route for bridgehead olefins (i.e., 33) of medium-sized carbocycles.