(3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-6-methylcyclohexanone | 187665-49-2

• 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: (3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-6-methylcyclohexanone
• 英文别名: (2E,3R,6R)-3-(3-chloroprop-1-en-2-yl)-6-methyl-2-(3-phenylmethoxypropylidene)cyclohexan-1-one
• CAS: 187665-49-2
• 化学式: C₂₀H₂₅ClO₂
• 分子量: 332.87
• InChiKey: STXYGNLUOADLLD-RSFIKGHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-6-methylcyclohexanone 在 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 samarium diiodide 、 2,3-二甲基-2-丁基硼烷 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 103.5h， 生成 (1S,4R,7R,8R)-11-[(E)-3-benzyloxypropylidene]-7-(methoxymethoxy)-8-methyl-2-methylenebicyclo[5.3.1]undecan-4-ol
  参考文献：
  名称：

  Efficient construction of 8-membered ring framework of vinigrol through SmI2-induced coupling cyclization

  摘要：

  The 8-membered ring framework of vinigrol, a unique tricyclic diterpene isolated as a novel antihypertensive compound from a culture of Virgaria nigra, was efficiently synthesized employing an SmI2-induced intramolecular coupling. It is particularly noteworthy that the 8-membered carbocycle was cyclized in quantitative yields under non-high-dilution conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00885-6
• 作为产物：
  描述：

  (+)-二氢香芹酮 在 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-6-methylcyclohexanone
  参考文献：
  名称：

  Efficient construction of 8-membered ring framework of vinigrol through SmI2-induced coupling cyclization

  摘要：

  The 8-membered ring framework of vinigrol, a unique tricyclic diterpene isolated as a novel antihypertensive compound from a culture of Virgaria nigra, was efficiently synthesized employing an SmI2-induced intramolecular coupling. It is particularly noteworthy that the 8-membered carbocycle was cyclized in quantitative yields under non-high-dilution conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00885-6

文献信息

• Construction of 8-Membered Ring Skeleton of Vinigrol <i>via</i> SmI₂-Promoted Barbier Coupling
  作者：M. Kito、T. Sakai、H. Shirahama、M. Miyashita、F. Matsuda

  DOI：10.1055/s-1997-748

  日期：1997.2

  The 8-membered ring framework of vinigrol, a unique tricyclic diterpene isolated as a novel antihypertensive compound from a culture of Virgaria nigra, was efficiently synthesized employing an SmI2-induced intramolecular Barbier coupling.

  vinigrol是一种从黑刺头菌培养物中分离出的独特三环二萜，是一种新型降压化合物，其8元环骨架采用SmI2诱导的分子内Barbier偶联反应高效合成。
• Efficient construction of 8-membered ring framework of vinigrol through SmI2-induced coupling cyclization
  作者：Fuyuhiko Matsuda、Makoto Kito、Toshinari Sakai、Naoko Okada、Masaaki Miyashita、Haruhisa Shirahama

  DOI：10.1016/s0040-4020(99)00885-6

  日期：1999.12

  The 8-membered ring framework of vinigrol, a unique tricyclic diterpene isolated as a novel antihypertensive compound from a culture of Virgaria nigra, was efficiently synthesized employing an SmI2-induced intramolecular coupling. It is particularly noteworthy that the 8-membered carbocycle was cyclized in quantitative yields under non-high-dilution conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.