(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal | 256441-00-6

• 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: (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal
• 英文别名: 3-[(1R,2E,3R,6R)-3-(3-chloroprop-1-en-2-yl)-1-(methoxymethoxy)-2-[3-[(4-methoxyphenyl)methoxy]propylidene]-6-methylcyclohexyl]propanal
• CAS: 256441-00-6
• 化学式: C₂₆H₃₇ClO₅
• 分子量: 465.03
• InChiKey: VWYICJYTYJSMJI-QRSPTJBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal 在 吡啶 、 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (1S,4R,7R,8R)-11-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-7-(methoxymethoxy)-8-methyl-2-methlenebicyclo[5.3.1]undecan-4-yl acetate
  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 吡啶 、 4-二甲氨基吡啶 、 2,3-二甲基-2-丁基硼烷 、 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 戴斯-马丁氧化剂 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 107.0h， 生成 (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal
  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

• 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.