Hexyl-cis-propenyl-ether | 6145-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Hexyl-cis-propenyl-ether
• 英文别名: (Z)-1-(prop-1-en-1-yloxy)hexane；1-[(Z)-prop-1-enoxy]hexane
• CAS: 6145-82-0
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: CWLCAARCOJSNGN-YWEYNIOJSA-N

物化性质

• 沸点：
  171.8±9.0 °C(Predicted)
• 密度：
  0.803±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-二甲基-1-丁烯 、 Hexyl-cis-propenyl-ether 在 C₂₂H₂₅N₂Ni⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以71%的产率得到
  参考文献：
  名称：

  （NHC）NiH催化的带有α-烯烃的乙烯基醚的区域发散性交叉氢化烯基化：1,2-和1,3-双取代的烯丙基醚的合成

  摘要：

  乙烯基醚（1）与α-烯烃（2）的交叉氢化烯基化首先通过一组[NHC-Ni（烯丙基）] BAr F（NHC = N-杂环卡宾）催化剂实现。通过使用不同尺寸的NHC，可以高度选择性地获得1,2-和1,3-二取代的烯丙基醚。相比之下，化学选择性（即1为受体，2为施主）主要受催化剂与底物相互作用的电子效应控制。与较小的烯烃相比，在立体上较大的烯烃（2）被用作优选的给体。这种电子效应也作为第一尾-头横hydroalkenylations的基础1 与乙烯基硅烷或硼酸酯。

  DOI：

  10.1002/anie.201712693
• 作为产物：
  描述：

  烯丙基正己基醚 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以92%的产率得到Hexyl-cis-propenyl-ether
  参考文献：
  名称：

  Isomerization of Allyl Ethers Initiated by Lithium Diisopropylamide

  摘要：

  Lithium diisopropylamide (LDA) promotes virtually quantitative conversion of allylic ethers to (Z)-propenyl ethers. It was discovered that allylic ethers can be isomerized efficiently with very high stereoselectivity to (Z)-propenyl ethers by LDA in THF at room temperature. The reaction time for the conversion increases with more sterically hindered allylic ethers. Different amides were also compared with LDA for their ability to effect this isomerization.

  DOI：

  10.1021/ol102029u

文献信息

• Facile O-Deallylation of Allyl Ethers via S_N2‘ Reaction with <i>tert</i>-Butyllithium
  作者：William F. Bailey、Michael D. England、Michael J. Mealy、Charnsak Thongsornkleeb、Lisa Teng

  DOI：10.1021/ol991342g

  日期：2000.2.1

  [reaction: see text] Allylic ethers are converted to the corresponding alcohol or phenol in virtually quantitative yield at temperatures below ambient simply by stirring a hydrocarbon solution of the ether with 1 molar equiv of tert-butyllithium. The reaction, which produces 4,4-dimethyl-1-pentene as a coproduct, most likely involves an S(N)2' attack of the organolithium on the allyl ether.

  [反应：见正文]仅通过将醚的烃溶液与1摩尔当量的叔丁基锂搅拌，即可在几乎低于环境温度的温度下以几乎定量的产率将烯丙基醚转化为相应的醇或苯酚。该反应产生4,4-二甲基-1-戊烯作为副产物，最有可能涉及有机锂对烯丙基醚的S（N）2'攻击。
• Erythromycin a derivatives and method for the preparation of the same
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0272110A2

  公开（公告）日：1988-06-22

  Erythromycin A derivativ es represented by the general formula wherein R¹ is a group of the formula R⁷CH₂- (wherein R⁷ is a hydrogen group or a lower alkyl group) or a group of the formula R⁸O- (wherein R⁸ is a lower alkyl group), R² is R⁸, a cycloalkyl group, a phenyl group or an aralkyl group, or R² and R₇ together form an alkylene group, R³ is a hydrogen atom, a lower alkyl group, a phenyl group or an aralkyl group, or R³ and R⁷ together form an alkylene group, or R² and R³ together form an alkylene group, R⁴ is a lower alkyl group, R⁵ is a substituted silyl group, and R⁶ is a hydrogen atom or R₅, are useful as intermediates for the synthesis of antibacterial agents.

  由通式表示的红霉素 A 衍生物 其中 R¹ 是式 R⁷CH₂- 的基团（其中 R⁷ 是氢基或低级烷基）或式 R⁸O- 的基团（其中 R⁸ 是低级烷基），R² 是 R⁸、环烷基、苯基或芳烷基，或 R² 和 R₇ 共同形成一个亚烷基，R³ 是氢原子、R⁴是低级烷基，R⁵是取代的硅烷基，R⁶是氢原子或 R₅，可作为合成抗菌剂的中间体。
• Isomerization of Allyl Ethers Initiated by Lithium Diisopropylamide
  作者：Chicheung Su、Paul G. Williard

  DOI：10.1021/ol102029u

  日期：2010.12.3

  Lithium diisopropylamide (LDA) promotes virtually quantitative conversion of allylic ethers to (Z)-propenyl ethers. It was discovered that allylic ethers can be isomerized efficiently with very high stereoselectivity to (Z)-propenyl ethers by LDA in THF at room temperature. The reaction time for the conversion increases with more sterically hindered allylic ethers. Different amides were also compared with LDA for their ability to effect this isomerization.
• (NHC)NiH-Catalyzed Regiodivergent Cross-Hydroalkenylation of Vinyl Ethers with α-Olefins: Syntheses of 1,2- and 1,3-Disubstituted Allyl Ethers
  作者：Weihao Chen、Yang Li、Yang Chen、Chun-Yu Ho

  DOI：10.1002/anie.201712693

  日期：2018.3.1

  (i.e., 1 as acceptor and 2 as donor) was controlled mostly by electronic effects through the catalyst–substrate interaction. Sterically bulkier alkenes (2) were used as preferred donors compared to smaller alkenes. This electronic effect also served as a basis for the first tail‐to‐head cross‐hydroalkenylations of 1 with either a vinyl silane or boronic ester.

  乙烯基醚（1）与α-烯烃（2）的交叉氢化烯基化首先通过一组[NHC-Ni（烯丙基）] BAr F（NHC = N-杂环卡宾）催化剂实现。通过使用不同尺寸的NHC，可以高度选择性地获得1,2-和1,3-二取代的烯丙基醚。相比之下，化学选择性（即1为受体，2为施主）主要受催化剂与底物相互作用的电子效应控制。与较小的烯烃相比，在立体上较大的烯烃（2）被用作优选的给体。这种电子效应也作为第一尾-头横hydroalkenylations的基础1 与乙烯基硅烷或硼酸酯。