(2S,3S,4R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylenecyclohexanone | 527755-53-9

• 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: (2S,3S,4R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylenecyclohexanone
• 英文别名: (2S,3S,4R)-2-(1,5-dimethylhex-1-enyl)-3-methoxy-4-(4-methoxybenzyloxy)-6-methylenecyclohexanone；(2S,3S,4R)-3-methoxy-4-[(4-methoxyphenyl)methoxy]-2-[(E)-6-methylhept-2-en-2-yl]-6-methylidenecyclohexan-1-one
• CAS: 527755-53-9
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: YCTFRWDYIPCWAK-UXAUJCPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylenecyclohexanone 在 镍 正丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 5.25h， 生成 (3R,4S,5S,6R,8R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-8-methyl-1-oxaspiro[2.5]octan-6-ol
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+
• 作为产物：
  描述：

  1-[(1R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-((E)-1,5-dimethyl-hex-1-enyl)-6-methoxy-4-triethylsilanyloxy-cyclohex-3-enyloxymethyl]-4-methoxy-benzene 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以70 mg的产率得到(2S,3S,4R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylenecyclohexanone
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+

文献信息

• US6803382B2
  申请人：——

  公开号：US6803382B2

  公开（公告）日：2004-10-12
• MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues
  作者：Vincent Rodeschini、Jean-Guy Boiteau、Pierre Van de Weghe、Céline Tarnus、Jacques Eustache

  DOI：10.1021/jo035065+

  日期：2004.1.1

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.