4-carboxy-13-(4,4-dimethyloxazolin-2-yl)[2.2]paracyclophane | 308366-32-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4-carboxy-13-(4,4-dimethyloxazolin-2-yl)[2.2]paracyclophane
• 英文别名: 12-(4,4-dimethyl-5H-1,3-oxazol-2-yl)tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene-5-carboxylic acid
• CAS: 308366-32-7
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: RQURKWMSXZQVFP-UHFFFAOYSA-N

物化性质

• 沸点：
  536.6±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-carboxy-13-(4,4-dimethyloxazolin-2-yl)[2.2]paracyclophane 在 盐酸 、 氯化亚砜 、 sodium azide 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 45.0h， 生成 4-amino-13-carbomethoxy[2.2]paracyclophane
  参考文献：
  名称：

  Oxazoline Mediated Routes to a Unique Amino-acid, 4-Amino-13-carboxy[2.2]paracyclophane, of Planar Chirality

  摘要：

  Efficient syntheses leading to 4-amino-13-carboxy[2.2]paracyclophane and derivatives are described. Novel oxazolinyl[2.2]paracyclophanes are used as intermediates and the oxazolinyl and amide groups are shown to be strong psi-geminal directing groups. Compounds with potential as catalysts have been made. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00644-x
• 作为产物：
  描述：

  对二甲苯二聚体 在 氯化亚砜 、 溴 、 碘 、 铁粉 、 magnesium 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 78.0h， 生成 4-carboxy-13-(4,4-dimethyloxazolin-2-yl)[2.2]paracyclophane
  参考文献：
  名称：

  Oxazoline Mediated Routes to a Unique Amino-acid, 4-Amino-13-carboxy[2.2]paracyclophane, of Planar Chirality

  摘要：

  Efficient syntheses leading to 4-amino-13-carboxy[2.2]paracyclophane and derivatives are described. Novel oxazolinyl[2.2]paracyclophanes are used as intermediates and the oxazolinyl and amide groups are shown to be strong psi-geminal directing groups. Compounds with potential as catalysts have been made. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00644-x

文献信息

• An Unusual Transannular Rearrangement of a [2.2]Paracyclophane Derivative to Yield the First [6.2.2]Cyclophane
  作者：Andrew Pelter、Anne Harrison-Marchand、Anderson Maxwell、Baldwin Mootoo、Alicia Reid、Simon J. Coles、Michael B. Hursthouse

  DOI：10.1135/cccc20020471

  日期：——

  A unique transannular interaction in the [2.2]paracyclophane series that involves the disruption of an oxazoline on one of the aromatic rings by a ψ-geminal carboxyl group on the adjacent ring is described. The result is the linking of the two benzene rings by the formation of a new interannular ring containing an ester and a secondary amide linkage leading to the first [6.2.2]cyclophane.

  [2.2]对二联苯系列中的一种独特的横环间相互作用被描述为涉及通过邻近环上的ψ-对羟基羧基团破坏一个芳香环上的氧杂环。结果是通过形成一个新的环间环，其中包含一个酯和一个次酰胺键，将两个苯环连接起来，形成了第一个[6.2.2]环联苯。
• Oxazoline Mediated Routes to a Unique Amino-acid, 4-Amino-13-carboxy[2.2]paracyclophane, of Planar Chirality
  作者：Anne Marchand、Anderson Maxwell、Baldwin Mootoo、Andrew Pelter、Alicia Reid

  DOI：10.1016/s0040-4020(00)00644-x

  日期：2000.9

  Efficient syntheses leading to 4-amino-13-carboxy[2.2]paracyclophane and derivatives are described. Novel oxazolinyl[2.2]paracyclophanes are used as intermediates and the oxazolinyl and amide groups are shown to be strong psi-geminal directing groups. Compounds with potential as catalysts have been made. (C) 2000 Elsevier Science Ltd. All rights reserved.