methyl (1S,2R)-2-[4-(2-chloroethoxy)phenyl]-1,2-diphenylcyclopropane-1-carboxylate | 264620-31-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl (1S,2R)-2-[4-(2-chloroethoxy)phenyl]-1,2-diphenylcyclopropane-1-carboxylate
• CAS: 264620-31-7
• 化学式: C₂₅H₂₃ClO₃
• 分子量: 406.909
• InChiKey: ZAUCQPNUQCQASA-JWQCQUIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R)-2-[4-(2-chloroethoxy)phenyl]-1,2-diphenylcyclopropane-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以93%的产率得到(1S,2R)-2-[4-(2-chloroethoxy)phenyl]-1,2-diphenyl-1-(hydroxymethyl)-cyclopropane
  参考文献：
  名称：

  Stereoselectivity of Methyl Aryldiazoacetate Cyclopropanations of 1,1-Diarylethylene. Asymmetric Synthesis of a Cyclopropyl Analogue of Tamoxifen

  摘要：

  Dirhodium tetrakis(S(N-dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4))-catalyzed decomposition of methyl phenyldiazoacetate in the presence of 1,1-diarylethylenes results in intermolecular cyclopropanation with high enantioselectivity (up to 99% ee) and moderate diastereoselectivity (up to 80% de). The reaction was applied to the asymmetric synthesis of a cyclopropyl analogue of tamoxifen.

  DOI：

  10.1021/ol005563u
• 作为产物：
  描述：

  4-羟基-二苯甲酮 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 正丁基锂 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 21.0h， 生成 methyl (1S,2R)-2-[4-(2-chloroethoxy)phenyl]-1,2-diphenylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Stereoselectivity of Methyl Aryldiazoacetate Cyclopropanations of 1,1-Diarylethylene. Asymmetric Synthesis of a Cyclopropyl Analogue of Tamoxifen

  摘要：

  Dirhodium tetrakis(S(N-dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4))-catalyzed decomposition of methyl phenyldiazoacetate in the presence of 1,1-diarylethylenes results in intermolecular cyclopropanation with high enantioselectivity (up to 99% ee) and moderate diastereoselectivity (up to 80% de). The reaction was applied to the asymmetric synthesis of a cyclopropyl analogue of tamoxifen.

  DOI：

  10.1021/ol005563u

文献信息

• Stereoselectivity of Methyl Aryldiazoacetate Cyclopropanations of 1,1-Diarylethylene. Asymmetric Synthesis of a Cyclopropyl Analogue of Tamoxifen
  作者：Huw M. L. Davies、Tadamichi Nagashima、James L. Klino

  DOI：10.1021/ol005563u

  日期：2000.3.1

  Dirhodium tetrakis(S(N-dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4))-catalyzed decomposition of methyl phenyldiazoacetate in the presence of 1,1-diarylethylenes results in intermolecular cyclopropanation with high enantioselectivity (up to 99% ee) and moderate diastereoselectivity (up to 80% de). The reaction was applied to the asymmetric synthesis of a cyclopropyl analogue of tamoxifen.