(4R,5Z)-5-(2,2-dimethylpropylidene)-2-hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one | 462116-86-5

• 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: (4R,5Z)-5-(2,2-dimethylpropylidene)-2-hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one
• CAS: 462116-86-5
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: FPOJRZQTUDZRCF-ZVHGMHCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (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 、 邻二氯苯 为溶剂， 反应 17.5h， 生成 (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：

  (E)-2-methyl-1-morpholin-4-yl-3-phenylprop-2-en-1-one 、 (aR)-4,4-dimethyl-penta-1,2-dienyl N,N-diisopropylcarbamate 在 正丁基锂 、 四甲基乙二胺 、 盐酸 作用下， 以 甲苯 、 乙醇 为溶剂， 反应 2.5h， 以74%的产率得到(4R,5Z)-5-(2,2-dimethylpropylidene)-2-hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis of Enantioenriched 5-Alkylidene-2-cyclopentenones from Chiral Allenyl Carbamates: Generation of a Chiral Lithium Allenolate and Allylic Activation for a Conrotatory 4π-Electrocyclization

  摘要：

  DOI：

  10.1002/1521-3773(20020503)41:9<1532::aid-anie1532>3.0.co;2-j

文献信息

• Asymmetric Cyclopentannelation:  Camphor-Derived Auxiliary
  作者：Paul E. Harrington、Tsuyoshi Murai、Chester Chu、Marcus A. Tius

  DOI：10.1021/ja020591o

  日期：2002.8.1

  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.
• Synthesis of Enantioenriched 5-Alkylidene-2-cyclopentenones from Chiral Allenyl Carbamates: Generation of a Chiral Lithium Allenolate and Allylic Activation for a Conrotatory 4π-Electrocyclization
  作者：Carsten Schultz-Fademrecht、Marc A. Tius、Stefan Grimme、B. Wibbeling、Dieter Hoppe

  DOI：10.1002/1521-3773(20020503)41:9<1532::aid-anie1532>3.0.co;2-j

  日期：2002.5.3