(3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione | 209625-83-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione
• CAS: 209625-83-2
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: FCADIUBKTXEUJK-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione 在 lithium aluminium tetrahydride 、 silica gel 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-[[(3R,4R)-1-cyclohexyl-4-[(2-hydroxynaphthalen-1-yl)methylideneamino]pyrrolidin-3-yl]iminomethyl]naphthalen-2-ol
  参考文献：
  名称：

  The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3,4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes

  摘要：

  The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural L-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.015
• 作为产物：
  描述：

  环己胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 (3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione
  参考文献：
  名称：

  The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3,4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes

  摘要：

  The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural L-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.015

文献信息

• The first enantioselective syntheses of vicinal difluoropyrrolidines and the first catalytic asymmetric synthesis mediated by the C2 symmetry of a –CHFCHF– unit
  作者：Charles M. Marson、Robert C. Melling

  DOI：10.1039/a801718b

  日期：——

  The first enantiopure vicinal difluorides of C2 symmetry have been prepared by the introduction of fluorine at both centres in a single operation; the first asymmetric synthesis using a catalyst whose chirality depends on organofluorine asymmetry is described.

  通过在一次操作中在两个中心引入氟，制备了第一个 C2 对称的对映体纯邻位二氟化物；描述了使用其手性取决于有机氟不对称性的催化剂的第一个不对称合成。
• Enantioselective Syntheses of <i>trans</i>-3,4-Difluoropyrrolidines and Investigation of Their Applications in Catalytic Asymmetric Synthesis
  作者：Charles M. Marson、Robert C. Melling

  DOI：10.1021/jo0513414

  日期：2005.11.1

  Asymmetric Syntheses of enantiopure trans-3,4-difluoropyrrolidines have been prepared by the introduction of fluorine at both centers in a single operation; asymmetric epoxidations and additions to benzaldehyde were conducted using catalysts whose chirality depends on organofluorine asymmetry.