rel-(1R,2R,6S,7E,11E)-1-Isopropenyl-6-<(tert-butyldimethylsilyl)oxy>-8,12-dimethyl-7,11-cyclotetradecadien-3-yn-2-ol | 121747-21-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: rel-(1R,2R,6S,7E,11E)-1-Isopropenyl-6-<(tert-butyldimethylsilyl)oxy>-8,12-dimethyl-7,11-cyclotetradecadien-3-yn-2-ol
• 英文别名: (1S,5R,6E,10E,14S)-5-[tert-butyl(dimethyl)silyl]oxy-7,11-dimethyl-14-prop-1-en-2-ylcyclotetradeca-6,10-dien-2-yn-1-ol
• CAS: 121747-21-5
• 化学式: C₂₅H₄₂O₂Si
• 分子量: 402.693
• InChiKey: AUTLDTUCBRYLAP-RVJXFJEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  rel-(1R,2R,6S,7E,11E)-1-Isopropenyl-6-<(tert-butyldimethylsilyl)oxy>-8,12-dimethyl-7,11-cyclotetradecadien-3-yn-2-ol 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (9E,13E)-(5S,6R)-6-Isopropenyl-5-methoxymethoxy-9,13-dimethyl-cyclotetradeca-2,3,9,13-tetraenone
  参考文献：
  名称：

  A mild method for the synthesis of furans. Application to 2,5-bridged furano macrocyclic compounds

  摘要：

  DOI：

  10.1021/jo00298a012
• 作为产物：
  描述：

  (2E,6E,10E)-3,7,11-Trimethyl-13-oxa-2,6,10-cycloheptadecatrien-15-yn-1-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 生成 rel-(1R,2R,6S,7E,11E)-1-Isopropenyl-6-<(tert-butyldimethylsilyl)oxy>-8,12-dimethyl-7,11-cyclotetradecadien-3-yn-2-ol
  参考文献：
  名称：

  A mild method for the synthesis of furans. Application to 2,5-bridged furano macrocyclic compounds

  摘要：

  DOI：

  10.1021/jo00298a012

文献信息

• Synthesis of 6-hydroxycembrane precursors by conformationally controlled diastereoselective [2,3] wittig ring contraction
  作者：James A. Marshall、Edward D. Robinson、Jacques Lebreton

  DOI：10.1016/0040-4039(88)85289-4

  日期：1988.1

  [2,3] Wittig ring contraction of the alkoxy substituted 17-membered allylic propargylic ethers 8 and 10 gives the trans/syn products 11 and 12 as the major diastereoisomers.

  [2，3]烷氧基取代的17元烯丙基炔丙基醚8和10的Wittig环收缩得到作为主要非对映异构体的反式/同式产物11和12。
• Synthesis of 12-, 14-, and 16-membered propargylic alcohols through Lewis acid-promoted ene cyclization
  作者：James A. Marshall、Marc W. Andersen

  DOI：10.1021/jo00067a024

  日期：1993.7

  The scope of the Lewis acid-promoted ene cyclization has been expanded to include 12-, 14-, and 16-membered rings. Thus, the ynals 1.8, 2.5, and 3.5 undergo efficient type-I cyclization upon addition to 1.0 equiv of EtAlCl2 in CH2Cl2 at -78-degrees-C. The epoxy ynal 4.3 undergoes pinacol rearrangement under these conditions. However, treatment with a 1:1 mixture of Et2AlCl and EtAlCl2 effects conversion to the cyclic products 4.4/4.5 (92:8) in satisfactory yield. Facile type-II cyclizations readily achieved with ynals 5.7, 6.4, 7.6, and 8.3 with EtAlCl2 as the Lewis acid. In the latter case, a 16-membered propargylic alcohol was produced in 84% yield.
• Synthesis of the tumor-inhibitory tobacco constituents .alpha.- and .beta.-2,7,11-cembratriene-4,6-diol by diastereoselective [2,3] Wittig ring contraction
  作者：James A. Marshall、Edward D. Robinson、Jacques Lebreton

  DOI：10.1021/jo00288a038

  日期：1990.1
• MARSHALL, JAMES A.;ROBINSON, EDWARD D., TETRAHEDRON LETT., 30,(1989) N, C. 1055-1058
  作者：MARSHALL, JAMES A.、ROBINSON, EDWARD D.

  DOI：——

  日期：——