cis-1-(hydroxymethyl)-3-phenylcyclobutane | 69584-48-1

• 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: cis-1-(hydroxymethyl)-3-phenylcyclobutane
• CAS: 69584-48-1
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: UDBCHONGSGQBQN-JGZJWPJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  methyl 3-chloro-3-phenylcyclobutane-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 trans-1-(hydroxymethyl)-3-phenylcyclobutane 、 cis-1-(hydroxymethyl)-3-phenylcyclobutane
  参考文献：
  名称：

  Experimental and calculated activation parameters for ring opening of the 1-bicyclo[1.1.1]pentyl radical: the effect of bridgehead substituents

  摘要：

  Ring opening of the 1-bicyclo[1.1.1]pentyl, 3-pentyl-1-bicyclo[1.1.1]pentyl, and 3-carbomethoxy-1-bicyclo[1.1.1]pentyl radicals has been studied by experiment and by molecular orbital theory. Our results indicate that the parent system 1a is extremely reluctant to ring open, with an energy barrier of at least 26 kcal mol-1. The ester- and phenyl-substituted radicals rearrange somewhat more readily, with barriers of about 25 and 21 kcal mol-1, respectively. This trend is also observed in the molecular orbital treatment of these processes. Previous reports that include radical rearrangements of this type must now be reconsidered in light of our new data.

  DOI：

  10.1021/jo00015a018

文献信息

• NOVEL HYDROXAMIC ACID AND N-HYDROXYUREA DERIVATIVES AND THEIR USE
  申请人：PFIZER INC.

  公开号：EP0559743B1

  公开（公告）日：1995-03-08
• US6291520B1
  申请人：——

  公开号：US6291520B1

  公开（公告）日：2001-09-18
• Experimental and calculated activation parameters for ring opening of the 1-bicyclo[1.1.1]pentyl radical: the effect of bridgehead substituents
  作者：Ernest W. Della、Paul E. Pigou、Carl H. Schiesser、Dennis K. Taylor

  DOI：10.1021/jo00015a018

  日期：1991.7

  Ring opening of the 1-bicyclo[1.1.1]pentyl, 3-pentyl-1-bicyclo[1.1.1]pentyl, and 3-carbomethoxy-1-bicyclo[1.1.1]pentyl radicals has been studied by experiment and by molecular orbital theory. Our results indicate that the parent system 1a is extremely reluctant to ring open, with an energy barrier of at least 26 kcal mol-1. The ester- and phenyl-substituted radicals rearrange somewhat more readily, with barriers of about 25 and 21 kcal mol-1, respectively. This trend is also observed in the molecular orbital treatment of these processes. Previous reports that include radical rearrangements of this type must now be reconsidered in light of our new data.