(+/-)-evuncifer ether | 136734-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (+/-)-evuncifer ether
• 英文别名: (1R,4S,8S,9R)-2,2,4,8-tetramethyl-3-oxatricyclo[6.2.2.04,9]dodecane
• CAS: 136734-35-5
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: XTWXRRVDVNEGRE-UXOAXIEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2α,4aβ,8α,8aβ)-(+/-)-1-(decahydro-8-hydroxy-4a,8-dimethyl-2-naphthalenyl)ethanol 在 吡啶 、 nicotinium dichromate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 (+/-)-evuncifer ether
  参考文献：
  名称：

  Synthesis of all stereoisomers of eudesm-11-en-4-ol. 2. Total synthesis of selin-11-en-4.alpha.-ol, intermedeol, neointermedeol, and paradisiol. First total synthesis of amiteol

  摘要：

  The syntheses of (+/-)-selin-11-en-4-alpha-ol (5), (+/-)-intermedeol (6), (+/-)-neointermedeol (7), (+/-)-amiteol (9), and the four remaining unnatural stereoisomers (+/-)-paradisiol (8), (+/-)-7-epi-amiteol (10), (+/-)-5-epi-neointermedeol (11), and (+/-)-5-epi-paradisiol (12) are described. In addition, the related (+/-)-evuncifer ether (25) has been prepared. The syntheses started from the octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenones 1-4. The reaction sequence employed for the synthesis of 5, 7, 9, and 12 involved Wittig reaction, oxidative hydroboration, oxidation, equilibration, and olefination. For the synthesis of 6, 8, 10, and 11 the interim equilibration step was omitted. The oxidative hydroboration was the key step in these syntheses.

  DOI：

  10.1021/jo00026a012

文献信息

• Biomimetic cyclization of hedycaryol derivatives. Unexpected cyclization of phenyl sulfides with methyl iodide
  作者：Mitsuaki Kodama、Kazuaki Shimada、Shô Itô

  DOI：10.1016/s0040-4039(01)90367-3

  日期：1981.1

  Four isomeric hedycaryol phenyl sulfides, when reacted with Mel, yielded eudesmol derivatives with different stereochemistry from that of the acid cyclization products of the corresponding hedycaryols. New stereoisomers of α- and β-eudesmols, β-dehydroparadisiol and a defensive substance of termite were synthesized. Nephthenol phenyl sulfide yielded a 14-membered tetraene.

  当四种异构体的海苏糖基苯硫醚与Mel反应时，会产生具有与相应的海苏糖醇的酸环化产物不同的立体化学的化学式的udedesmol衍生物。合成了新的α-和β-大麦醇的立体异构体，β-脱氢对二酚和白蚁的防御物质。乙烯酚苯硫醚生成14元四烯。
• Sesquiterpene Glycosides and Phenylpropanoid Esters from <i>Phonus arborescens</i> (<i>Carthamus arborescens</i>)
  作者：Alejandro F. Barrero、Pilar Arteaga、José F. Quílez、Ignacio Rodríguez、M. Mar Herrador

  DOI：10.1021/np970122d

  日期：1997.10.1

  The tert-butylmethyl ether extract of the aerial parts of Phonus arborescens (L.) G. Lopez (Carthamus arborescens L.) afforded three new sesquiterpene glycosides, 10-epi-gamma-eudesmol beta-D-fucopyranoside (1), 10-epi-gamma-eudesmol 2'-O-acetyl-beta-D-fucopyranoside (2), and 4,5-dioxo-10-epi-4,5-seco-gamma-eudesmol 2'-O-acetyl-beta-D-fucopyranoside (3), together with two new phenylpropanoid esters, 3-(3,4-dihydroxyphenyl)propyl myristate (4) and 3-(3,4-dihydroxyphenyl)propyl palmitate (5) in addition to a series of known compounds. The structures of the new compounds were established by spectroscopic and chemical methods.