(+)-3-(1-nitrocyclopentyl) cycloheptanone | 160012-09-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (+)-3-(1-nitrocyclopentyl) cycloheptanone
• 英文别名: (3R)-3-(1-nitrocyclopentyl)cycloheptan-1-one
• CAS: 160012-09-9
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: MIHMFPZVLNXHDB-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-(-)-2,3-丁二醇 、 (+)-3-(1-nitrocyclopentyl) cycloheptanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with trans-4,5-Methano-l-proline

  摘要：

  The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with > 99% ee and excellent chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities. Proline hydroxamic acid and its trans-4,5-methano-L-proline hydroxamic acid are also effective organocatalysts in the addition of 2-nitropropane to 2-cyclohexenone (75% and 81% ee, respectively).

  DOI：

  10.1021/ol0618407
• 作为产物：
  描述：

  2-环庚烯-1-酮 、 硝基环戊烷 在 trans-4,5-methano-L-proline 氯仿 、 2,5-dimethyl-piperazine 作用下， 反应 144.0h， 以56%的产率得到(+)-3-(1-nitrocyclopentyl) cycloheptanone
  参考文献：
  名称：

  Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with trans-4,5-Methano-l-proline

  摘要：

  The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with > 99% ee and excellent chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities. Proline hydroxamic acid and its trans-4,5-methano-L-proline hydroxamic acid are also effective organocatalysts in the addition of 2-nitropropane to 2-cyclohexenone (75% and 81% ee, respectively).

  DOI：

  10.1021/ol0618407

文献信息

• Catalytic asymmetric Michael addition of nitroalkane to enone and enal
  作者：Masahiko Yamaguchi、Tai Shiraishi、Yoshihiro Igarashi、Masahiro Hirama

  DOI：10.1016/0040-4039(94)88290-8

  日期：1994.10

  L-Proline rubidium salt catalyzes the asymmetric Michael addition of nitroalkanes to enones and an enal. (R)-Adducts were obtained from cyclic (Z)-enones and (S)-adducts from acyclic (E)-enones. Bu3SnH treatment of the products replaced the nitro group with hydrogen atom. The overall transformation allows the asymmetric alkylation of enones at the β-carbon atom.

  L-脯氨酸rub盐催化硝基烷烃向烯酮和烯醛的不对称迈克尔加成反应。从环状（Z）-烯酮获得（R）-加合物，从无环（E）-烯酮获得（S）-加合物。Bu 3 SnH处理的产物用氢原子取代了硝基。整体转化允许β-碳原子上烯酮的不对称烷基化。
• Catalytic Asymmetric Conjugate Addition of Nitroalkanes to Cycloalkenones
  作者：Stephen Hanessian、Vinh Pham

  DOI：10.1021/ol000170g

  日期：2000.9.1

  Nitroalkanes add to cyclic and acyclic enones in an enantioselective manner in the presence of catalytic quantities of L-proline and trans-2,5-dimethylpiperazine as excess additive.

  在催化量的L-脯氨酸和反式2,5-二甲基哌嗪作为过量添加剂存在下，硝基烷以对映选择性的方式添加到环状和无环烯酮中。
• Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with <i>trans</i>-4,5-Methano-<scp>l</scp>-proline
  作者：Stephen Hanessian、Zhihui Shao、Jayakumar S. Warrier

  DOI：10.1021/ol0618407

  日期：2006.10.1

  The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with > 99% ee and excellent chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities. Proline hydroxamic acid and its trans-4,5-methano-L-proline hydroxamic acid are also effective organocatalysts in the addition of 2-nitropropane to 2-cyclohexenone (75% and 81% ee, respectively).