4-(4,4-dimethyloxazolin-2-yl)[2.2]paracyclophane | 308366-30-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4-(4,4-dimethyloxazolin-2-yl)[2.2]paracyclophane
• 英文别名: 4,4-dimethyl-2-(5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)-5H-1,3-oxazole
• CAS: 308366-30-5；404588-93-8
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: NDPHTBMZCFBLNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4,4-dimethyloxazolin-2-yl)[2.2]paracyclophane 在 盐酸 、 正丁基锂 、 溴 、 铁粉 作用下， 以 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 54.0h， 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 、 乙腈 为溶剂， 反应 38.0h， 生成 4-(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

• The synthesis of homochiral ligands based on [2.2]paracyclophane
  作者：Andrew Pelter、Baldwin Mootoo、Anderson Maxwell、Alicia Reid

  DOI：10.1016/s0040-4039(01)01808-1

  日期：2001.11

  A new ortho-lithiation of homochiral 4-N,N-diethylamido[2.2]paracyclophane 8 is the key to the production of a wide variety of 4,5-disubstituted homochiral ligands. psi -Geminal bromination of 8 proceeds in high yields and the resulting bromide may be converted into a variety of 4,13-disubstituted ligands. The o-lithiation and psi -geminal reactions can be used sequentially to give 4,5,12-trisubstituted compounds in which two liganding groups have the same geometrical relationship as in 'Phanephos'(TM). Homochiral oxazolines with only planar chirality have been made, one of which has been shown to be an effective catalyst for the Heck reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.