3-tert-Butyl-1-(bromomethyl)bicyclo<1.1.1>pentane | 162374-92-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 3-tert-Butyl-1-(bromomethyl)bicyclo<1.1.1>pentane
• 英文别名: 1-(Bromomethyl)-3-tert-butylbicyclo[1.1.1]pentane
• CAS: 162374-92-7
• 化学式: C₁₀H₁₇Br
• 分子量: 217.149
• InChiKey: YQJBCEWDKVVSBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-tert-Butyl-1-(bromomethyl)bicyclo<1.1.1>pentane 在 sodium tetrahydroborate 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 48.0h， 以74%的产率得到1-tert-Butyl-3-methylbicyclo<1.1.1>pentane
  参考文献：
  名称：

  Ring-Opening of (Cyclobutylmethyl)lithium and [(3-tert-Butyl-1-bicyclo[1.1.1]pentyl)methyl]lithium

  摘要：

  The ring-opening of (cyclobutylmethyl)lithium (1) to 4-pentenyllithium (2) has been investigated in a solvent system composed of isooctane-dibutyl ether (3:2 by volume). The isomerization of 1 to 2, which is much more rapid than is cleavage of the corresponding Grignard reagent, is characterized by the following activation parameters: E(a) = 14.7 +/- 1.2 kcal/mol, ln A = 21.6 +/- 2.5; Delta H-double dagger = 14.2 +/- 1.2 kcal/mol, Delta S-double dagger = -17.3 +/- 5 eu. The two-step isomerization of [(3-tert-butyl-1-bicyclo[1.1.1]pentyl)methyl]lithium (5) to 4-tert-butyl-2-methylidene-4-pentenyllithium (7) via [(1-tert-butyl-3-methylidenecyclobutyl)methyl]lithium (6) in pentane-diethyl ether involves a very rapid initial ring-opening of 5 to 6 (t(1/2) < 15 min at -131 degrees C) followed by a slower isomerization of 6 to 7 (t(1/2) approximate to 24 min at -7.7 degrees C).

  DOI：

  10.1021/jo00107a005
• 作为产物：
  描述：

  3-tert-butylbicyclo<1.1.1>pentane-1-carboxylic acid 在 吡啶 、 lithium aluminium tetrahydride 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 3-tert-Butyl-1-(bromomethyl)bicyclo<1.1.1>pentane
  参考文献：
  名称：

  Ring-Opening of (Cyclobutylmethyl)lithium and [(3-tert-Butyl-1-bicyclo[1.1.1]pentyl)methyl]lithium

  摘要：

  The ring-opening of (cyclobutylmethyl)lithium (1) to 4-pentenyllithium (2) has been investigated in a solvent system composed of isooctane-dibutyl ether (3:2 by volume). The isomerization of 1 to 2, which is much more rapid than is cleavage of the corresponding Grignard reagent, is characterized by the following activation parameters: E(a) = 14.7 +/- 1.2 kcal/mol, ln A = 21.6 +/- 2.5; Delta H-double dagger = 14.2 +/- 1.2 kcal/mol, Delta S-double dagger = -17.3 +/- 5 eu. The two-step isomerization of [(3-tert-butyl-1-bicyclo[1.1.1]pentyl)methyl]lithium (5) to 4-tert-butyl-2-methylidene-4-pentenyllithium (7) via [(1-tert-butyl-3-methylidenecyclobutyl)methyl]lithium (6) in pentane-diethyl ether involves a very rapid initial ring-opening of 5 to 6 (t(1/2) < 15 min at -131 degrees C) followed by a slower isomerization of 6 to 7 (t(1/2) approximate to 24 min at -7.7 degrees C).

  DOI：

  10.1021/jo00107a005

文献信息

• Ring-Opening of (Cyclobutylmethyl)lithium and [(3-tert-Butyl-1-bicyclo[1.1.1]pentyl)methyl]lithium
  作者：William F. Bailey、Eric R. Punzalan、Ernest W. Della、Dennis K. Taylor

  DOI：10.1021/jo00107a005

  日期：1995.1

  The ring-opening of (cyclobutylmethyl)lithium (1) to 4-pentenyllithium (2) has been investigated in a solvent system composed of isooctane-dibutyl ether (3:2 by volume). The isomerization of 1 to 2, which is much more rapid than is cleavage of the corresponding Grignard reagent, is characterized by the following activation parameters: E(a) = 14.7 +/- 1.2 kcal/mol, ln A = 21.6 +/- 2.5; Delta H-double dagger = 14.2 +/- 1.2 kcal/mol, Delta S-double dagger = -17.3 +/- 5 eu. The two-step isomerization of [(3-tert-butyl-1-bicyclo[1.1.1]pentyl)methyl]lithium (5) to 4-tert-butyl-2-methylidene-4-pentenyllithium (7) via [(1-tert-butyl-3-methylidenecyclobutyl)methyl]lithium (6) in pentane-diethyl ether involves a very rapid initial ring-opening of 5 to 6 (t(1/2) < 15 min at -131 degrees C) followed by a slower isomerization of 6 to 7 (t(1/2) approximate to 24 min at -7.7 degrees C).