6,6-(Ethylenedioxy)-2-methylhept-1-ene | 38237-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6-(Ethylenedioxy)-2-methylhept-1-ene
• 英文别名: 6,6-Ethylenedioxy-2-methyl-hept-1-ene；2-methyl-2-(4-methylpent-4-enyl)-1,3-dioxolane
• CAS: 38237-34-2
• 化学式: C₁₀H₁₈O₂
• mdl: MFCD11554006
• 分子量: 170.252
• InChiKey: VZUGAJIKBVMJFY-UHFFFAOYSA-N

物化性质

• 沸点：
  90-95 °C(Press: 10 Torr)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  6,6-(Ethylenedioxy)-2-methylhept-1-ene 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 6-甲基-6-庚烯-2-酮
  参考文献：
  名称：

  Synthesis of

  摘要：

  一种合成1RS，4SR，5RS-4-（4,8-二甲基-5-羟基-7-诺酮-1-基）-4-甲基-3,8-二氧杂双环[3.2.1]辛烷-1-乙酸的方法。该酸是zoapatanol的衍生物之一，是zoapatle植物中的活性成分之一，并作为子宫疏通剂活性。

  公开号：

  US04237055A1
• 作为产物：
  描述：

  乙酰丙酸甲酯 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 sodium acetate 、 sodium hydride 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 、 sodium iodide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 6,6-(Ethylenedioxy)-2-methylhept-1-ene
  参考文献：
  名称：

  Dhokte, U. P.; Rao, A. S., Synthetic Communications, 1988, vol. 18, # 8, p. 811 - 822

  摘要：

  DOI：

文献信息

• Organotellurides as a source of organometallics: application in the synthesis of (+/−)-frontalin
  作者：Alcindo A. Dos Santos、Renan S. Ferrarini、Jefferson L. Princival、João V. Comasseto

  DOI：10.1016/j.tetlet.2006.10.039

  日期：2006.12

  A masked lithium homoenolate, generated by tellurium/lithium exchange, was reacted with epoxides. The lithium compound was also converted into other organometallics such as Grignard, and cuprates and the reactivity of those organometallics with epoxides was evaluated. The same building block was employed in the synthesis of (+/−)-frontalin.

  通过碲/锂交换产生的被掩盖的均烯酸锂与环氧化物反应。锂化合物也被转化为其他有机金属，例如格利雅（Grignard），并评估了铜酸盐和这些有机金属与环氧化物的反应性。在（+/-）-额叶蛋白的合成中使用了相同的结构单元。
• Chemoenzymatic Synthesis of (S)-(-)-Frontalin Using Bacterial Epoxide Hydrolases
  作者：Wolfgang Kroutil、Ingrid Osprian、Martin Mischitz、Kurt Faber

  DOI：10.1055/s-1997-1153

  日期：1997.2

  The pheromone (S)-(-)-frontalin (1) was synthesized in five steps in 94% ee via a chemoenzymatic route. In the key step, 2-methyl-2-(pent-4-enyl)oxirane [(±)-7a] was resolved employing lyophilized cells of Rhodococcus equi IFO 3730 (E=39).

  信息素(S)-(-)-前腺素(1)通过化学酶法路线在五个步骤中合成，得到的对映体纯度为94%。关键步骤中，采用冷冻干燥的耐盐芽孢杆菌 R. equi IFO 3730 (E=39) 对2-甲基-2-(戊-4-烯基)环氧化物[(±)-7a]进行了分离。
• Synthesis of
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04237055A1

  公开（公告）日：1980-12-02

  A method of synthesizing 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicy clo [3.2.1]octane-1-acetic acid. The acid is a derivative of the natural product zoapatanol, one of the active ingredients in the zoapatle plant, and is active as a utero-evacuant agent.

  一种合成1RS，4SR，5RS-4-（4,8-二甲基-5-羟基-7-诺酮-1-基）-4-甲基-3,8-二氧杂双环[3.2.1]辛烷-1-乙酸的方法。该酸是zoapatanol的衍生物之一，是zoapatle植物中的活性成分之一，并作为子宫疏通剂活性。
• Synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo(3.2.1)octane-1-acetic acid and intermediates
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0021775A1

  公开（公告）日：1981-01-07

  A method of synthesizing -1RS,4SR,5RS-4-(4,8 -dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1]octane-1-acetic acid. The acid is a derivative of the natural product zoapatanol, one of the active ingredients in the zoapatle plant, and is active as a utero-evacuant agent.

  一种合成-1RS,4SR,5RS-4-(4,8-二甲基-5-羟基-7-壬烯-1-基)-4-甲基-3,8-二氧杂环[3.2.1]辛烷-1-乙酸的方法。 该酸是天然产品zoapatanol的衍生物，zoapatanol是zoapatle植物中的活性成分之一，具有子宫缓释剂的活性。
• Nonracemic frontalin via copper- and palladium-based skeletal construction and the asymmetric dihydroxylation
  作者：Braulio Santiago、John A. Soderquist

  DOI：10.1021/jo00048a014

  日期：1992.10

  The new higher order organocuprate, Li2Cu(CN)(C(OMe):CH2)2, prepared through a Sn --> Li --> Cu transmetalation sequence, was found to efficiently couple with allyl bromide producing 2-methoxy-1,4-pentadiene (3) which is efficiently converted to the ketal 4. Hydroboration of 4 with 9-BBN-H and the selective oxidation of this adduct with trimethylamine N-oxide (TMANO) produces 9-oxa-10-borabicyclo[3.3.2]decane 5, which undergoes Pd-catalyzed cross coupling with 2-bromopropene producing 6, thereby accomplishing the construction of the frontalin carbon skeleton in 63% overall yield from allyl bromide. The Os-based dihydroxylation of 6 followed by ketalization either produces the racemic pheromone ((+/-)-1) or, with the Sharpless catalytic asymmetric dihydroxylation (dihydroquinine ligand) procedure, results in the selective formation of the S enantiomer in 35% ee. The de determined from the C-13 NMR spectra of the diastereomeric Mosher's monoesters (9) was found to provide useful corroborative information on the optical purity of the intermediate 1,2-diols 7.