(R)-2-Allyloxy-5-[2,2-dimethyl-prop-(Z)-ylidene]-3-methyl-4-phenyl-cyclopent-2-enone | 462116-96-7

• 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: (R)-2-Allyloxy-5-[2,2-dimethyl-prop-(Z)-ylidene]-3-methyl-4-phenyl-cyclopent-2-enone
• 英文别名: (4R,5Z)-5-(2,2-dimethylpropylidene)-3-methyl-4-phenyl-2-prop-2-enoxycyclopent-2-en-1-one
• CAS: 462116-96-7
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: CRYWVKWZKLSCQD-NOCRFKNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-Allyloxy-5-[2,2-dimethyl-prop-(Z)-ylidene]-3-methyl-4-phenyl-cyclopent-2-enone 以 邻二氯苯 为溶剂， 反应 0.5h， 以70%的产率得到(3R,4R)-3-Allyl-5-[2,2-dimethyl-prop-(E)-ylidene]-3-methyl-4-phenyl-cyclopentane-1,2-dione
  参考文献：
  名称：

  Asymmetric Cyclopentannelation:  Camphor-Derived Auxiliary

  摘要：

  The scope of an enantioselective cyclopentannelation reaction that makes use of allenyl ether-derived nucleophiles has been probed. The enantioselectivity is induced by a traceless chiral auxiliary that is easily derived from camphor. It has been shown that for gamma-substituted allene ethers that are axially chiral, very high enantiomeric excesses of cyclopentenone products are observed in the matched cases. Two fundamentally different mechanisms are observed, one for the cyclizations of allenyl ketones (see eq 7), the other for the cyclizations of allenyl alcohols (see eq 11). The methodology is versatile, efficient, and well-suited for applications in synthesis.

  DOI：

  10.1021/ja020591o
• 作为产物：
  描述：

  3-溴丙烯 、 (4R,5Z)-5-(2,2-dimethylpropylidene)-2-hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one 在 N,N-二异丙基乙胺 作用下， 以 硝基甲烷 为溶剂， 反应 17.0h， 以90%的产率得到(R)-2-Allyloxy-5-[2,2-dimethyl-prop-(Z)-ylidene]-3-methyl-4-phenyl-cyclopent-2-enone
  参考文献：
  名称：

  Asymmetric Cyclopentannelation:  Camphor-Derived Auxiliary

  摘要：

  The scope of an enantioselective cyclopentannelation reaction that makes use of allenyl ether-derived nucleophiles has been probed. The enantioselectivity is induced by a traceless chiral auxiliary that is easily derived from camphor. It has been shown that for gamma-substituted allene ethers that are axially chiral, very high enantiomeric excesses of cyclopentenone products are observed in the matched cases. Two fundamentally different mechanisms are observed, one for the cyclizations of allenyl ketones (see eq 7), the other for the cyclizations of allenyl alcohols (see eq 11). The methodology is versatile, efficient, and well-suited for applications in synthesis.

  DOI：

  10.1021/ja020591o