(2R,5S)-5-isopropyl-2-{[(triisopropylsilyl)oxy]methyl}cyclohexanone | 211797-34-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,5S)-5-isopropyl-2-{[(triisopropylsilyl)oxy]methyl}cyclohexanone
• 英文别名: (2R,5S)-5-propan-2-yl-2-[tri(propan-2-yl)silyloxymethyl]cyclohexan-1-one
• CAS: 211797-34-1
• 化学式: C₁₉H₃₈O₂Si
• 分子量: 326.595
• InChiKey: CXGRJAKMBDDRIO-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  (2R,5S)-5-isopropyl-2-{[(triisopropylsilyl)oxy]methyl}cyclohexanone 在 吡啶 、 氢氧化钾 、 四丁基氟化铵 、 三氧化硫吡啶 、 二异丁基氢化铝 、 magnesium 、 二甲基亚砜 作用下， 以 甲醇 为溶剂， 生成 (4S)-4-isopropyl-2-(pent-4-enyl)cyclohex-1-en-1-ylmethyl acetate
  参考文献：
  名称：

  分子内Pd催化的Zn-ene反应合成（-）-红四烯

  摘要：

  A highly diastereoselective synthesis of (-)-Erythrodiene was achieved via an intramolecular Pd-catalyzed Znene reaction as the key step. It was found that Pd(OAc)(2)/Bu3P was a superior catalyst for this reaction to Pd(PPh3)(4). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00991-5
• 作为产物：
  描述：

  (S)-(-)-紫苏醇 在 platinum(IV) oxide 咪唑 、 sodium hydroxide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 dimethyl sulfide borane 、 氢气 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2R,5S)-5-isopropyl-2-{[(triisopropylsilyl)oxy]methyl}cyclohexanone
  参考文献：
  名称：

  分子内Pd催化的Zn-ene反应合成（-）-红四烯

  摘要：

  A highly diastereoselective synthesis of (-)-Erythrodiene was achieved via an intramolecular Pd-catalyzed Znene reaction as the key step. It was found that Pd(OAc)(2)/Bu3P was a superior catalyst for this reaction to Pd(PPh3)(4). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00991-5

文献信息

• Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamolvia Intramolecular Pd-Catalyzed Allylzincation
  作者：Wolfgang Oppolzer、Felix Flachsmann

  DOI：10.1002/1522-2675(20010228)84:2<416::aid-hlca416>3.0.co;2-k

  日期：2001.2.28

  Two spirobicyclic sesquiterpenoids, (-)-erythrodiene (1) and (+)-7-epispirojatamol (30),were synthesized in enantiomerically pure form via an intramolecular allylzincation process. The allylzinc species were formed in the presence of Et,Zn via transmetallation of a catalytically generated allylpalladium intermediate. Several Pd catalysts were tested for this transformation, and [Pd(OAc)(2)/Bu3P(1 equiv.) was found to be, by far, the most effective. Whereas the preparation of 1 involved allylzincation of a tethered terminal olefin. 30 was formed via a novel intramolecular allylzincation of a methyl ketone. Both reactions showed the same stereochemical preference. yielding the spirobicyclic products in 95:5 and 4:1 diastereoisomer ratios, respectively.
• Synthesis of (-)-erythrodiene via intramolecular Pd-catalyzed Zn-ene reaction
  作者：W. Oppolzer、F. Flachsmann

  DOI：10.1016/s0040-4039(98)00991-5

  日期：1998.7

  A highly diastereoselective synthesis of (-)-Erythrodiene was achieved via an intramolecular Pd-catalyzed Znene reaction as the key step. It was found that Pd(OAc)(2)/Bu3P was a superior catalyst for this reaction to Pd(PPh3)(4). (C) 1998 Elsevier Science Ltd. All rights reserved.