(E,E)-1-chloro-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadiene | 63058-28-6

• 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: (E,E)-1-chloro-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadiene
• 英文别名: 3-[(3E,7E)-9-chloro-3,7-dimethylnona-3,7-dienyl]-2,2-dimethyloxirane
• CAS: 63058-28-6
• 化学式: C₁₅H₂₅ClO
• 分子量: 256.816
• InChiKey: AQOXDDSSTOWJLV-WAAHFECUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,E)-1-chloro-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadiene 在 叔丁基过氧化氢 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium chlorite 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 tert-butyl-ammonium fluoride 、 草酰氯 、 bis(η5-cyclopentadienyl)chlorohafnium hydride 、 1,3-diazabicyclo[5.4.0]-undec-7-ene 、 diazaborolidine 、 碘 、 戴斯-马丁氧化剂 、 过碘酸 、 1,1,2,3,3-pentaisopropylguanidine 、 三乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 88.75h， 生成 (6E,10E)-(3aS,12aR)-3-Isopropylidene-6,10,12a-trimethyl-3,3a,4,5,8,9,12,12a-octahydro-1H-cyclopentacycloundecen-2-one
  参考文献：
  名称：

  First Enantioselective Total Synthesis of a Naturally Occurring Dolabellane. Revision of Absolute Configuration

  摘要：

  DOI：

  10.1021/ja9536779
• 作为产物：
  描述：

  反式,反式-金合欢醇 在 N-溴代丁二酰亚胺(NBS) 、 水 、 potassium carbonate 、 甲基磺酰氯 、 lithium chloride 作用下， 生成 (E,E)-1-chloro-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadiene
  参考文献：
  名称：

  First Enantioselective Total Synthesis of a Naturally Occurring Dolabellane. Revision of Absolute Configuration

  摘要：

  DOI：

  10.1021/ja9536779

文献信息

• Synthesis of (6E)-8-Thia- and (14E)-13-Thia-2,3-oxidosqualene: Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase
  作者：Yi Feng Zheng、Allan C. Oehlschlager、Peter G. Hartman

  DOI：10.1021/jo00098a048

  日期：1994.9

  Synthesis of (6E)-8-thia-2,3-oxidosqualene (22) and (14E)-13-thia-2,3-oxidosqualene (34) as inhibitors of 2,3-oxidosqualene-lanosterol cyclase are reported. Synthesis of 22 required the stereospecific generation of a vinyl sulfide. This was achieved by a new coupling of a benzenethiosulfonate (15) and a lithiated vinyl iodide (18). Synthesis of 34 involved similar coupling of benzenethiosulfonate 29 with lithium reagent obtained from vinyl iodide 33. The required (E)-vinyl iodides 18 and 33 were prepared by zirconium-catalyzed carboalumination of 4-pentyn-1-ol, (16) and 2,6-dimethyl-2(E),6(E)-dien-10-yne (32) respectively. Both 22 and 34 inhibited 2,3-oxidosqualene-lanosterol cyclase from Candida albicans with IC50 values of 0.68 and 45 mu M, respectively.
• Muto, Shin-Etsu; Nishimura, Yutaka; Mori, Kenji, European Journal of Organic Chemistry, 1999, # 9, p. 2159 - 2165
  作者：Muto, Shin-Etsu、Nishimura, Yutaka、Mori, Kenji

  DOI：——

  日期：——
• Concise total synthesis of (±)-palominol and (±)-dolabellatrienone via a dianion-accelerated oxy-cope rearrangement
  作者：E.J. Corey、Robert S. Kania

  DOI：10.1016/s0040-4039(97)10614-1

  日期：1998.2

  A short synthesis of (+/-)-palominol (1) and (+/-)-dolabellatrienone (2) starting from farnesol is reported. Noteworthy steps include an intramolecular pinacol coupling to form a 15-membered carbocyclic diol and subsequent dianion-accelerated oxy-Cope rearrangement to form the 11,5-trans-fused ring system of the dolabellanes. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Reinforcing effect of bi- and tri-cyclopolyprenols on ‘primitive’ membranes made of polyprenyl phosphates
  作者：Nigel Ribeiro、Stéphane Streiff、Denis Heissler、Mourad Elhabiri、Anne Marie Albrecht-Gary、Michiko Atsumi、Mari Gotoh、Laurent Désaubry、Yoichi Nakatani、Guy Ourisson

  DOI：10.1016/j.tet.2007.01.076

  日期：2007.4

  Cholesterol plays the role of membrane reinforcer in eukaryotes, whereas hopanoids play the same role in bacteria. Which components could have reinforced 'primitive' membranes? We describe here an efficient biomimetic synthesis of bi- and tri-cyclopolyprenols and demonstrate that these compounds reinforce the membranes of polyprenyl phosphate, which we speculated as 'primitive' membranes. (c) 2007 Elsevier Ltd. All rights reserved.
• First Enantioselective Total Synthesis of a Naturally Occurring Dolabellane. Revision of Absolute Configuration
  作者：E. J. Corey、Robert S. Kania

  DOI：10.1021/ja9536779

  日期：1996.1.1