(2R,4aR,6S,9aS)-6-Ethyl-2-(4-methoxy-phenyl)-4a,6,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene | 217939-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,4aR,6S,9aS)-6-Ethyl-2-(4-methoxy-phenyl)-4a,6,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene
• CAS: 217939-79-2
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: WSOXMJSRPBYTAK-QMCVQRASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,9aS)-6-Ethyl-2-(4-methoxy-phenyl)-4a,6,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 三乙基硼氢化锂 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 (2R,4aR,6S,7R,9aS)-6-Ethyl-2-(4-methoxy-phenyl)-hexahydro-1,3,5-trioxa-benzocyclohepten-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：

  (S)-2-[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-butyraldehyde 在 Grubbs catalyst first generation 正丁基锂 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.0h， 生成 (2R,4aR,6S,9aS)-6-Ethyl-2-(4-methoxy-phenyl)-4a,6,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene
  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