7-(3-Butenyl)-7-methyl-1,4-dioxaspiro[4.5]decane | 127488-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(3-Butenyl)-7-methyl-1,4-dioxaspiro[4.5]decane
• 英文别名: 7-But-3-enyl-7-methyl-1,4-dioxaspiro[4.5]decane
• CAS: 127488-38-4
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: GCTUIEJDTHLGID-UHFFFAOYSA-N

物化性质

• 沸点：
  275.5±15.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(3-Butenyl)-7-methyl-1,4-dioxaspiro[4.5]decane 在 palladium on activated charcoal 四氢吡咯 、 盐酸 、 lithium aluminium tetrahydride 、 jones reagent 、 二甲基硫 、 氢气 、 臭氧 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 、 丙酮 为溶剂， -78.0~25.0 ℃ 、275.79 kPa 条件下， 反应 57.0h， 生成 (αR^*,1R^*,3aR^*,7aS^*)-Hexahydro-α-isopropyl-3a-methyl-7-methylene-1-indanacetic acid
  参考文献：
  名称：

  Synthetic approaches to the axane family of sesquiterpenoids. Total synthesis of (dl)-axamide-4, (dl)-axisonitrile-4, and (dl)-axisothiocyanate-4

  摘要：

  Two methods for the preparation of perhydroindan 7 are described. One involves an intramolecular free radical cyclization in a key step and proceeds in 13 steps and 9% yield from anisole (9). The other involves an intramolecular conjugate addition mediated by pyrrolidine (28 --> 7) and proceeds in five steps and 30% overall yield from vinylogous ester 29. Two unsuccessful attempts to convert 7 into axane sesquiterpenoids 1-6 are described. The synthesis of axanes 4-6 was achieved using a potassium tert-butoxide catalyzed cyclization of a dienoic keto ester as a key step (47 + 48 --> 49). Conversion of alpha,beta-unsaturated ester 49 to vinyl isocyanate 57 was accomplished using a Curtius rearrangement and reduction of 57 with lithium triethylborohydride completed the synthesis of axamide-4 (4). The preparation of axisonitrile-4 (5) and axisothiocyanate-4 (6) from 4 is also described.

  DOI：

  10.1021/jo00033a023
• 作为产物：
  描述：

  3-乙氧基-2-环己烯-1-酮 在 对甲苯磺酸 、 copper(I) bromide 、 原甲酸三甲酯 作用下， 以 苯 为溶剂， 反应 10.75h， 生成 7-(3-Butenyl)-7-methyl-1,4-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Synthetic approaches to the axane family of sesquiterpenoids. Total synthesis of (dl)-axamide-4, (dl)-axisonitrile-4, and (dl)-axisothiocyanate-4

  摘要：

  Two methods for the preparation of perhydroindan 7 are described. One involves an intramolecular free radical cyclization in a key step and proceeds in 13 steps and 9% yield from anisole (9). The other involves an intramolecular conjugate addition mediated by pyrrolidine (28 --> 7) and proceeds in five steps and 30% overall yield from vinylogous ester 29. Two unsuccessful attempts to convert 7 into axane sesquiterpenoids 1-6 are described. The synthesis of axanes 4-6 was achieved using a potassium tert-butoxide catalyzed cyclization of a dienoic keto ester as a key step (47 + 48 --> 49). Conversion of alpha,beta-unsaturated ester 49 to vinyl isocyanate 57 was accomplished using a Curtius rearrangement and reduction of 57 with lithium triethylborohydride completed the synthesis of axamide-4 (4). The preparation of axisonitrile-4 (5) and axisothiocyanate-4 (6) from 4 is also described.

  DOI：

  10.1021/jo00033a023

文献信息

• Total Synthesis of Allocyathin B₂, a Metabolite of Bird's Nest Fungi
  作者：Motoo Tori、Naoko Toyoda、Masakazu Sono

  DOI：10.1021/jo971514s

  日期：1998.1.1

  Allocyathin B-2 has been synthesized using aldol reactions for construction of rings A and B, introduction of the side chain for ring B, cyclization of the acetyl group into a lactone, and construction of the seven-membered diene aldehyde during the last step.
• HART, DAVID J.;LAI, CHIN-SHAN, SYNLETT.,(1989) N, C. 49-51
  作者：HART, DAVID J.、LAI, CHIN-SHAN

  DOI：——

  日期：——
• Synthetic approaches to the axane family of sesquiterpenoids. Total synthesis of (dl)-axamide-4, (dl)-axisonitrile-4, and (dl)-axisothiocyanate-4
  作者：Balan Chenera、Che Ping Chuang、David J. Hart、Chin Shan Lai

  DOI：10.1021/jo00033a023

  日期：1992.3

  Two methods for the preparation of perhydroindan 7 are described. One involves an intramolecular free radical cyclization in a key step and proceeds in 13 steps and 9% yield from anisole (9). The other involves an intramolecular conjugate addition mediated by pyrrolidine (28 --> 7) and proceeds in five steps and 30% overall yield from vinylogous ester 29. Two unsuccessful attempts to convert 7 into axane sesquiterpenoids 1-6 are described. The synthesis of axanes 4-6 was achieved using a potassium tert-butoxide catalyzed cyclization of a dienoic keto ester as a key step (47 + 48 --> 49). Conversion of alpha,beta-unsaturated ester 49 to vinyl isocyanate 57 was accomplished using a Curtius rearrangement and reduction of 57 with lithium triethylborohydride completed the synthesis of axamide-4 (4). The preparation of axisonitrile-4 (5) and axisothiocyanate-4 (6) from 4 is also described.