(1aR,3aS,5R,7aR,9S,9aR)-9-Ethyl-5-(4-methoxy-phenyl)-octahydro-1,4,6,8-tetraoxa-benzo[a]cyclopropa[e]cyclooctene | 217939-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1aR,3aS,5R,7aR,9S,9aR)-9-Ethyl-5-(4-methoxy-phenyl)-octahydro-1,4,6,8-tetraoxa-benzo[a]cyclopropa[e]cyclooctene
• 英文别名: (1R,3S,4R,6R,9S,11R)-3-ethyl-11-(4-methoxyphenyl)-2,5,10,12-tetraoxatricyclo[7.4.0.04,6]tridecane
• CAS: 217939-94-1
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: RGDUTQVGQOGNQB-PVWHLQNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1aR,3aS,5R,7aR,9S,9aR)-9-Ethyl-5-(4-methoxy-phenyl)-octahydro-1,4,6,8-tetraoxa-benzo[a]cyclopropa[e]cyclooctene 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(2R,4aR,6S,7R,10aS)-6-Ethyl-2-(4-methoxy-phenyl)-octahydro-1,3,5-trioxa-benzocycloocten-7-ol
  参考文献：
  名称：

  Synthesis of medium-sized cyclic allylic ethers by ring-closing metathesis and subsequent elaboration to sub-units found in the brevetoxins and ciguatoxins

  摘要：

  Saturated and unsaturated seven- and eight-membered cyclic ethers of the type found in the brevetoxins and ciguatoxins have been prepared in enantiomerically pure form in 10 steps from a readily available chiral pool material. The key steps in this sequence are ring-closing metathesis of allylic ethers, and subsequent elaboration of the cyclic allylic ether products by stereoselective epoxide formation and ring-opening. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01825-5
• 作为产物：
  描述：

  在 bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 potassium tert-butylate 、 叔丁醇 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 49.25h， 生成 (1aR,3aS,5R,7aR,9S,9aR)-9-Ethyl-5-(4-methoxy-phenyl)-octahydro-1,4,6,8-tetraoxa-benzo[a]cyclopropa[e]cyclooctene
  参考文献：
  名称：

  Synthesis of medium-sized cyclic allylic ethers by ring-closing metathesis and subsequent elaboration to sub-units found in the brevetoxins and ciguatoxins

  摘要：

  Saturated and unsaturated seven- and eight-membered cyclic ethers of the type found in the brevetoxins and ciguatoxins have been prepared in enantiomerically pure form in 10 steps from a readily available chiral pool material. The key steps in this sequence are ring-closing metathesis of allylic ethers, and subsequent elaboration of the cyclic allylic ether products by stereoselective epoxide formation and ring-opening. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01825-5

文献信息

• Synthesis of medium-sized cyclic allylic ethers by ring-closing metathesis and subsequent elaboration to sub-units found in the brevetoxins and ciguatoxins
  作者：J.Stephen Clark、Olivier Hamelin、Richard Hufton

  DOI：10.1016/s0040-4039(98)01825-5

  日期：1998.11

  Saturated and unsaturated seven- and eight-membered cyclic ethers of the type found in the brevetoxins and ciguatoxins have been prepared in enantiomerically pure form in 10 steps from a readily available chiral pool material. The key steps in this sequence are ring-closing metathesis of allylic ethers, and subsequent elaboration of the cyclic allylic ether products by stereoselective epoxide formation and ring-opening. (C) 1998 Elsevier Science Ltd. All rights reserved.