(2R,4S,5R)-4-but-3-enyl-2-(4-methoxyphenyl)-5-[(3S)-pent-1-en-3-yl]oxy-1,3-dioxane | 186258-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S,5R)-4-but-3-enyl-2-(4-methoxyphenyl)-5-[(3S)-pent-1-en-3-yl]oxy-1,3-dioxane
• CAS: 186258-75-3
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: WSUMFJOPVJMICH-GSEOLPGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-4-but-3-enyl-2-(4-methoxyphenyl)-5-[(3S)-pent-1-en-3-yl]oxy-1,3-dioxane 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) 、 potassium tert-butylate 、 叔丁醇 作用下， 以 苯 为溶剂， 反应 37.25h， 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
• 作为产物：
  描述：

  (2R,4S,5R)-4-But-3-enyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-ol 在 lithium aluminium tetrahydride 、 正丁基锂 、 pyridine-SO3 complex 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4S,5R)-4-but-3-enyl-2-(4-methoxyphenyl)-5-[(3S)-pent-1-en-3-yl]oxy-1,3-dioxane
  参考文献：
  名称：

  通过闭环复分解合成短链毒素A中环亚单位的对映选择性

  摘要：

  已经开发了一种新的策略，用于对映异构合成短分子毒素A亚基的八元和九元环状醚。该策略涉及使用烯丙基醚的闭环复分解反应以实现环的构建。

  DOI：

  10.1016/s0040-4039(96)02233-2

文献信息

• Enantioselective synthesis of medium-ring sub-units of brevetoxin A by ring-closing metathesis
  作者：J. Stephen Clark、Jason G. Kettle

  DOI：10.1016/s0040-4039(96)02233-2

  日期：1997.1

  A new strategy for the enantioselective synthesis of eight- and nine-membered cyclic ethers corresponding to sub-units of brevetoxin A has been developed. The strategy involves the use of ring-closing metathesis reactions of allylic ethers to effect ring construction.

  已经开发了一种新的策略，用于对映异构合成短分子毒素A亚基的八元和九元环状醚。该策略涉及使用烯丙基醚的闭环复分解反应以实现环的构建。
• 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.