(1'R,3'aR,7'aR)-1'-(2-ethoxy-2-oxoethyl)spiro[1,3-dioxolane-2,7'-2,3,4,5,6,7a-hexahydro-1H-indene]-3'a-carboxylic acid | 139017-44-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1'R,3'aR,7'aR)-1'-(2-ethoxy-2-oxoethyl)spiro[1,3-dioxolane-2,7'-2,3,4,5,6,7a-hexahydro-1H-indene]-3'a-carboxylic acid
• CAS: 139017-44-0
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: BAGWPKTYHLBNQH-UXIGCNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1'R,3'aR,7'aR)-1'-(2-ethoxy-2-oxoethyl)spiro[1,3-dioxolane-2,7'-2,3,4,5,6,7a-hexahydro-1H-indene]-3'a-carboxylic acid 在 sodium tetrahydroborate 、 甲酸 、 草酰氯 、 偶氮二异丁腈 、 四溴化碳 、 水 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 33.67h， 生成 Ethyl (1R^*,3aS^*,7aR^*)-Hexahydro-3a-methyl-7-oxo-1-indanacetate
  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：

  (E)-5-((1R,5R,8S)-8-Iodo-5-methoxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-1-yl)-pent-2-enoic acid ethyl ester 在 palladium on activated charcoal 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 甲醇 、 苯 为溶剂， 生成 (1'R,3'aR,7'aR)-1'-(2-ethoxy-2-oxoethyl)spiro[1,3-dioxolane-2,7'-2,3,4,5,6,7a-hexahydro-1H-indene]-3'a-carboxylic 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