trans-3,4-epoxy-1-phenylphospholane-1-oxide | 85281-93-2

• 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: trans-3,4-epoxy-1-phenylphospholane-1-oxide
• 英文别名: 3,4-epoxy-1-phenylphospholane 1-oxide
• CAS: 85281-93-2
• 化学式: C₁₀H₁₁O₂P
• 分子量: 194.17
• InChiKey: NNLINXNWBRBQLO-DDFAGTSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-3,4-epoxy-1-phenylphospholane-1-oxide 在 硼烷四氢呋喃络合物 、 苯硅烷 、 仲丁基锂 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 (-)-4-hydroxy-1-phenyl-2-phospholene 1-borane
  参考文献：
  名称：

  Chiral base promoted enantioselective rearrangement of organophosphorus epoxides

  摘要：

  Cinchona alkaloids serve as effective chiral bases for enantioselective rearrangement of 3,4-epoxyphospholane oxides resulting in the formation of P,C-chirogenic 4-hydroxy-2-phospholene derivatives with up to 52% ee. A stereochemical course of the epoxide rearrangement involving anti beta-proton abstraction is proposed. 3,4-Epoxy-1-phospholane-borane rearranges to 4-hydroxy-2-phospholene-borane of 55% ee on treatment with sec-BuLi/sparteine base system. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.028
• 作为产物：
  描述：

  苯基磷杂环戊-3-烯 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 10.0h， 以84%的产率得到trans-3,4-epoxy-1-phenylphospholane-1-oxide
  参考文献：
  名称：

  Enantioselective desymmetrization of a phospholene meso-epoxide

  摘要：

  Cinchona alkaloids serve as effective chiral bases in the enantioselective rearrangement of 3-phospholene epoxide. The reaction results in the formation of a P,C-chirogenic 3-hydroxy-2-phospholene derivative with up to 52% e.e. A stereochemical course for the epoxide rearrangement involving anti-p-proton abstraction is implied. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00245-8

文献信息

• Bodalski, Ryszard; Janecki, Tomasz; Galdecki, Zdzislaw, Phosphorus and Sulfur and the Related Elements, 1982, vol. 14, p. 15 - 22
  作者：Bodalski, Ryszard、Janecki, Tomasz、Galdecki, Zdzislaw、Glowka, Marek

  DOI：——

  日期：——
• BODALSKI, RYSZARD;JANECKI, TOMASZ, BULL. POL. ACAD. SCI. CHEM., 35,(1987) N 11-12, 529-540
  作者：BODALSKI, RYSZARD、JANECKI, TOMASZ

  DOI：——

  日期：——
• Enantioselective desymmetrization of phospholene meso-epoxide by nucleophilic opening of the epoxide
  作者：Zbigniew Pakulski、K.Michał Pietrusiewicz

  DOI：10.1016/j.tetasy.2003.10.015

  日期：2004.1

  A convenient synthesis of enantioenriched P-stereogenic trans-3-hydroxy-4-azido- and trans-3-hydroxy-4-cyanophospholane oxides has been achieved by ring opening of 3,4-epoxy-1-phenylphospholane-1-oxide using trimethylsilyl azide and trimethylsilyl cyanide in the presence of salen-Al complex. The enantioselectivity of the studied asymmetric ring-opening reactions reached 72% in the best case. (C) 2003 Elsevier Ltd. All rights reserved.