1-(1-乙氧基乙氧基)-6-溴己烷 | 55491-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(1-乙氧基乙氧基)-6-溴己烷
• 英文名称: 1-(1-Ethoxyethoxy)-6-bromohexane
• 英文别名: 1-bromo-8-methyl-7,9-dioxaundecane；1-bromo-6-(1-ethoxyethoxy)hexane；11-bromo-3,5-dioxa-4-methyl-undecane；6-Bromo-1-(1'-ethoxyethoxy)hexane；6-Bromhexyl-1-ethoxy-ethylether；(1-Ethoxyethoxy)-6-bromohexane
• CAS: 55491-60-6
• 化学式: C₁₀H₂₁BrO₂
• 分子量: 253.18
• InChiKey: KOMCXRQUMPLJMW-UHFFFAOYSA-N

物化性质

• 沸点：
  260.6±20.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1-(1-乙氧基乙氧基)-6-溴己烷 在 Pd-BaSO₄ 吡啶 、 喹啉 、 盐酸 、 甲醇 、 六甲基磷酰三胺 、 三甲基氯硅烷 、 乙基溴化镁 、 氢气 、 乙二胺 、 sodium iodide 、 copper(l) chloride 、 lithium diisopropyl amide 作用下， 以 乙醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 4.0h， 生成 2-甲氧基-6-十五烷基苯甲酸乙酯
  参考文献：
  名称：

  Synthesis of polyunsaturated constituents of phenolic lipids

  摘要：

  The diene, (ZZ)-[(8,11)-pentadecadienyl]salicylic acid, (or 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl]benzoic acid), has been synthesised by two routes. In the first, the key intermediate methyl or ethyl 2-hydroxy-6-(7-bromoheptyl)benzoate has been converted to methyl or ethyl 2-hydroxy-6-(10-hydroxydec-8-ynyl)benzoate and thence by reaction of the corresponding bromide with 1-pentynylmagnesium bromide to methyl or ethyl 2-hydroxy-6-(pentadeca-8,11-dienyl)benzoate. Selective reduction afforded methyl or ethyl 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl]benzoate. An attempt to employ the Grignard reagent from methyl 2-methoxy-6-(non-8-ynyl)benzoate and reaction with 1-bromohex-2-yne was ineffective because of a side reaction of the former with ethylmagnesium bromide to give a ketone. In the third approach ethyl 2-methoxy-6-methylbenzoate was alkylated with 1-iodotetradeca-7,10-diyne and the product selectively reduced as before to the O-methyl ether ethyl ester. A variety of C-14 intermediates has been prepared for the derivation of the 8(E), 11(E), 8(E), 11(Z) and 8(2), 11(E) stereoisomers by the alkylation procedure. A similar methodology of alkylation can be adopted for obtaining corresponding trienes in which some progress has been made commencing with the synthesis of the 8(2),11(2),14 compound. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(96)02654-0
• 作为产物：
  描述：

  6-溴正己醇 、 乙烯基乙醚 在 二氯乙酸 作用下， 反应 12.0h， 以95%的产率得到1-(1-乙氧基乙氧基)-6-溴己烷
  参考文献：
  名称：

  苯硫基取代的1，n-二醇与甲苯-对-磺酸和甲苯-对-磺酰氯的重排合成环醚和烯丙基硫化物

  摘要：

   在两组条件下，一系列Phs-基团与一个OH基团相邻的1，n-二醇（n = 2至12）的重排产生了四种化合物，并以极佳的收率得到了单一化合物。链长的影响有助于理解不同的环化模式和重排机制。

  DOI：

  10.1039/a905498g

文献信息

• Method to inhibit ethylene responses in plants
  申请人：Jacobson Martin Richard

  公开号：US20050065033A1

  公开（公告）日：2005-03-24

  The present invention generally relates to methods of inhibiting ethylene responses in plants and plant materials, and particularly relates to methods of inhibiting various ethylene responses including plant maturation and degradation, by exposing plants to cyclopropene derivatives and compositions thereof wherein: 1) at least one substituent on the cyclopropene ring contains a carbocyclic or heterocyclic ring, or 2) . a substituent contains silicon, sulfur, phosphorous, or boron, or 3) least one substituent contains from one to four non-hydrogen atoms and at least one substituent contains more than four non-hydrogen atoms.

  本发明一般涉及抑制植物和植物材料中乙烯反应的方法，特别涉及通过将植物暴露于环丙烯衍生物和其组合物中来抑制各种乙烯反应，包括植物成熟和降解，其中：1）环丙烯环上至少一个取代基含有碳环或杂环，或2）一个取代基含有硅、硫、磷或硼，或3）至少一个取代基含有一到四个非氢原子，且至少一个取代基含有多于四个非氢原子。
• Synthesis of (Z)-14-Heptadecen-4-olide and (Z)-11-Pentadecen-4-olide, Sex Pheromone Analogues of Ostrinia nubilalis and Cydia molesta
  作者：Michal Hoskovec、David Šaman、Bohumír Koutek

  DOI：10.1135/cccc19941211

  日期：——

  The key step in the preparation of racemic (Z)-14-heptadecen-4-olide (VIa) and (Z)-11-pentadecen-4-olide (VIb), sex pheromone analogues of Ostrinia nubilalis and Cydia molesta, was efficient cross-coupling reaction of 3-methoxycarbonylpropanoyl chloride with corresponding (Z)-alkenylmagnesium bromides. The methyl 4-oxo-(Z)-14-heptadecenoate (Va) and methyl 4-oxo-(Z)-11-pentadecenoate (Vb) prepared in this way were converted by one-pot reaction using sodium borohydride in an ethanolic solution to the required (Z)-alken-4-olides (VIa, VIb).

  在制备(Z)-14-庚烯-4-酮内酯(VIa)和(Z)-11-戊烯-4-酮内酯(VIb)，即玉米螟和桃小食蛾的性信息素类似物的关键步骤是3-甲氧羰基丙酰氯与相应的(Z)-烯基溴化镁的高效交叉偶联反应。通过这种方法制备的甲基4-氧代-(Z)-14-庚烯酸酯(Va)和甲基4-氧代-(Z)-11-戊烯酸酯(Vb)通过乙醇溶液中的硼氢化钠的一锅法反应转化为所需的(Z)-烯-4-酮内酯(VIa, VIb)。
• Methods of blocking an ethylene response in plants using cyclopropene derivatives
  申请人：——

  公开号：US20010019995A1

  公开（公告）日：2001-09-06

  Methods of applying cyclopropene derivatives and compositions thereof to block ethylene receptors in plants are disclosed. One such method comprises applying to the plant an effective ethylene response-inhibiting amount of cyclopropene derivatives or compositions thereof. Also disclosed are methods of inhibiting abscission in plants, methods of prolonging the life of cut flowers, methods of inhibiting ripening of picked fruits, and methods of inhibiting ripening of picked vegetables.

  本发明揭示了应用环丙烯衍生物及其组合物来阻断植物中乙烯受体的方法。其中一种方法包括向植物施加足够的环丙烯衍生物或其组合物以抑制乙烯反应。还揭示了抑制植物脱落的方法、延长切花寿命的方法、抑制采摘水果成熟的方法以及抑制采摘蔬菜成熟的方法。
• α,α-Disubstituted Allyl Sulfones: An approach to the synthesis of vinyl-branched pheromone analogues
  作者：Michal Hoskovec、Bohumír Koutek、Josef Lazar、Ludvík Streinz、Eva Brožová、Blanka Kalinová、Jan Vrkoč

  DOI：10.1002/hlca.19940770510

  日期：1994.8.10

  The two-step alkylation of phenyl prop-2-enyl sulfone (1) with protected ω-bromoalkanols and 1-iodoalkanes (3; see Scheme 1) followed by a Pd-catalyzed desulfonylation with LiBH4 affords a 96:4 mixture of vinylbranched, protected alcohols and corresponding ethylidene-branched isomers (see Scheme 2; 4 and 5, respectively). By utilizing the large difference in reactivity of mono- and trisubstituted CC

  用受保护的ω-溴链烷醇和1-碘代烷烃（3 ;参见方案1）对苯基丙-2-烯基砜（1）进行两步烷基化，然后用LiBH 4进行Pd催化的脱磺酰化反应，得到96：4乙烯基支化的混合物，受保护的醇和相应的亚乙基支化的异构体（分别参见方案2；4和5）。通过利用单取代的和三取代的CC键对单线态氧的反应性的巨大差异，可通过光氧合轻松地从混合物中除去亚乙基衍生物。乙烯基支化的化合物对该反应是惰性的，可以方便地以高纯形式（99.5％）分离。 总产率为45％。
• METHOD TO INHIBIT ETHYLENE RESPONSES IN PLANTS
  申请人：Jacobson Richard Martin

  公开号：US20110190137A1

  公开（公告）日：2011-08-04

  The present invention generally relates to methods of inhibiting ethylene responses in plants and plant materials, and particularly relates to methods of inhibiting various ethylene responses including plant maturation and degradation, by exposing plants to cyclopropene derivatives and compositions thereof wherein: 1) at least one substituent on the cyclopropene ring contains a carbocyclic or heterocyclic ring, or 2) a substituent contains silicon, sulfur, phosphorous, or boron, or 3) least one substituent contains from one to four non-hydrogen atoms and at least one substituent contains more than four non-hydrogen atoms.

  本发明通常涉及抑制植物和植物材料中乙烯反应的方法，特别涉及通过将植物暴露于环丙烯衍生物和其组合物中来抑制各种乙烯反应，其中：1）环丙烯环上的至少一个取代基包含一个碳环或杂环，或2）取代基包含硅、硫、磷或硼，或3）至少一个取代基含有一到四个非氢原子，且至少一个取代基含有超过四个非氢原子。