((1R,3S,6S)-7,7-Dimethyl-4-methylene-bicyclo[4.1.0]hept-3-yl)-acetic acid ethyl ester | 879296-93-2

• 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: ((1R,3S,6S)-7,7-Dimethyl-4-methylene-bicyclo[4.1.0]hept-3-yl)-acetic acid ethyl ester
• 英文别名: ethyl 2-[(1R,3S,6S)-7,7-dimethyl-4-methylidene-3-bicyclo[4.1.0]heptanyl]acetate
• CAS: 879296-93-2
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: NJEIVAQPAOLNGT-SDDRHHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((1R,3S,6S)-7,7-Dimethyl-4-methylene-bicyclo[4.1.0]hept-3-yl)-acetic acid ethyl ester 在 高氯酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 73.0h， 生成 (1S,3S,8S,10R)-(+)-11,11-dimethyl-3-hydroxy-5-oxatricyclo[8.1.0.0^3,8]undecan-6-one
  参考文献：
  名称：

  Stereochemistry of terpene derivatives. Part 5: Synthesis of chiral lactones fused to a carane system—insect feeding deterrents

  摘要：

  Chiral iodo- 9, bromo- 10 and hydroxylactones 12 condensed with the carane system were obtained. In each case, the synthetic pathway led to an enantiomerically pure diastereoisomer to generate two stereogenic centers. Iodo- 9 and bromolactone 10 possess a gamma-lactone group while the hydroxylactone 12 possesses a delta-lactone moiety situated trans to the gein-dimethylcyclopropyl ring. The structures of the products were confirmed by X-ray crystallography. These lactones were tested for antifeedant activity against storage pest insects. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.11.025
• 作为产物：
  描述：

  (-)-(1S,6R)-7,7-dimethylbicyclo<4.1.0>hept-3-ene-3-carboxaldehyde 在 sodium tetrahydroborate 、 乙醇 、 丙酸 作用下， 反应 1.0h， 生成 ((1R,3S,6S)-7,7-Dimethyl-4-methylene-bicyclo[4.1.0]hept-3-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Stereochemistry of terpene derivatives. Part 5: Synthesis of chiral lactones fused to a carane system—insect feeding deterrents

  摘要：

  Chiral iodo- 9, bromo- 10 and hydroxylactones 12 condensed with the carane system were obtained. In each case, the synthetic pathway led to an enantiomerically pure diastereoisomer to generate two stereogenic centers. Iodo- 9 and bromolactone 10 possess a gamma-lactone group while the hydroxylactone 12 possesses a delta-lactone moiety situated trans to the gein-dimethylcyclopropyl ring. The structures of the products were confirmed by X-ray crystallography. These lactones were tested for antifeedant activity against storage pest insects. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.11.025

文献信息

• Stereochemistry of terpene derivatives. Part 5: Synthesis of chiral lactones fused to a carane system—insect feeding deterrents
  作者：Bożena Frąckowiak、Katarzyna Ochalik、Agata Białońska、Zbigniew Ciunik、Czesław Wawrzeńczyk、Stanisław Lochyński

  DOI：10.1016/j.tetasy.2005.11.025

  日期：2006.1

  Chiral iodo- 9, bromo- 10 and hydroxylactones 12 condensed with the carane system were obtained. In each case, the synthetic pathway led to an enantiomerically pure diastereoisomer to generate two stereogenic centers. Iodo- 9 and bromolactone 10 possess a gamma-lactone group while the hydroxylactone 12 possesses a delta-lactone moiety situated trans to the gein-dimethylcyclopropyl ring. The structures of the products were confirmed by X-ray crystallography. These lactones were tested for antifeedant activity against storage pest insects. (c) 2005 Published by Elsevier Ltd.