(1S,2R,4S,5R)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentane-1-carbaldehyde | 1114552-67-8

• 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: (1S,2R,4S,5R)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentane-1-carbaldehyde
• CAS: 1114552-67-8
• 化学式: C₂₈H₅₀O₅Si₂
• 分子量: 522.873
• InChiKey: JDOMBAUMJUMEMO-WVZMWUMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,4S,5R)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentane-1-carbaldehyde 在 Schwartz's reagent 、 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.09h， 生成
  参考文献：
  名称：

  Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

  摘要：

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

  DOI：

  10.1021/jo1019738
• 作为产物：
  描述：

  methyl (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-1-hydroxy-4-methylcyclopentane-1-carboxylate 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 Sudan Red B 、 四丁基碘化铵 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 27.25h， 生成 (1S,2R,4S,5R)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentane-1-carbaldehyde
  参考文献：
  名称：

  Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

  摘要：

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

  DOI：

  10.1021/jo1019738

文献信息

• Synthetic Studies toward Jatrophane Diterpenes from <i>Euphorbia characias</i>. Enantioselective Synthesis of (−)-15-<i>O</i>-Acetyl-3-<i>O</i>-propionyl-17-norcharaciol
  作者：Hannes Helmboldt、Martin Hiersemann

  DOI：10.1021/jo802581g

  日期：2009.2.20

  The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.
• Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators
  作者：Christoph Schnabel、Katja Sterz、Henrik Müller、Julia Rehbein、Michael Wiese、Martin Hiersemann

  DOI：10.1021/jo1019738

  日期：2011.1.21

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.