Adipinsaeure-bis-(2-chlor-allylester) | 762-19-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Adipinsaeure-bis-(2-chlor-allylester)
• 英文别名: adipic acid bis-(2-chloro-allyl ester)；Bis(2-chloroprop-2-enyl) hexanedioate；bis(2-chloroprop-2-enyl) hexanedioate
• CAS: 762-19-6
• 化学式: C₁₂H₁₆Cl₂O₄
• 分子量: 295.163
• InChiKey: DQUIOZNPISPLGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Adipinsaeure-bis-(2-chlor-allylester) 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以73%的产率得到2-chloroallyl 2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones

  摘要：

  The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)(3)-t-BuPHOX ligand, alpha-quaternary cyclopentanones were isolated in yields up to >99% with ee's up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.

  DOI：

  10.1021/acs.orglett.5b02376
• 作为产物：
  描述：

  己二酸 、 2-氯-2-丙烯-1-醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 16.0h， 以99%的产率得到Adipinsaeure-bis-(2-chlor-allylester)
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones

  摘要：

  The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)(3)-t-BuPHOX ligand, alpha-quaternary cyclopentanones were isolated in yields up to >99% with ee's up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.

  DOI：

  10.1021/acs.orglett.5b02376

文献信息

• US2159008
  申请人：——

  公开号：——

  公开（公告）日：——
• US2217673
  申请人：——

  公开号：——

  公开（公告）日：——
• Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones
  作者：Robert A. Craig、Steven A. Loskot、Justin T. Mohr、Douglas C. Behenna、Andrew M. Harned、Brian M. Stoltz

  DOI：10.1021/acs.orglett.5b02376

  日期：2015.11.6

  The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)(3)-t-BuPHOX ligand, alpha-quaternary cyclopentanones were isolated in yields up to >99% with ee's up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.