tetradeca-1,13-dien-4-ol | 114837-51-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tetradeca-1,13-dien-4-ol
• 英文别名: 1,13-tetradecadien-4-ol
• CAS: 114837-51-3
• 化学式: C₁₄H₂₆O
• 分子量: 210.36
• InChiKey: OXVBXRVUSRBHJR-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、乙醚、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tetradeca-1,13-dien-4-ol 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[10-(Oxiran-2-yl)-2-phenylmethoxydecyl]oxirane
  参考文献：
  名称：

  Pentacoordinate Organoaluminum Chemistry:  Catalytic Efficiency of Me₃Al in the Epoxide Cleavage with Alkynyllithiums

  摘要：

  A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoalluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (l-benzyloxy)-3-butene oxide (1), in toluene with PhC=CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at O degrees C for 5 h to furnish the alkynylation product, l-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-l-pentene oxide, which was not susceptible to nucleophile attack of PhC=CLi with catalytic Me3A1 under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature C-13 and Al-27 NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.

  DOI：

  10.1021/ja9842464
• 作为产物：
  描述：

  10-十一烯醛 在 platinum(II) chloride 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 19.0h， 生成 tetradeca-1,13-dien-4-ol
  参考文献：
  名称：

  Fuerstner, Alois; Voigtlaender, David, Synthesis, 2000, # 7, p. 959 - 969

  摘要：

  DOI：

文献信息

• Allylic alcohols as synthons of allylic carbanions. Palladium-catalyzed carbonyl allylation by allylic alcohols with tin dichloride
  作者：Yoshiro. Masuyama、Jun P. Takahara、Yasuhiko. Kurusu

  DOI：10.1021/ja00221a091

  日期：1988.6

  L'allylation des aldehydes est chimioselective et a ete effectuee en presence du groupement cetone

  L'allylation des aldehydes est chimioselective et a ete effectuee en 存在 du groupement cetone
• A Convenient One Pot Allylation of Aldehydes with Allylic Halides Prepared in Situ from Allylic Alcohols in the Presence of Metallic Bismuth
  作者：Norikazu Miyoshi、Mami Nishio、Shunsuke Murakami、Tomohiro Fukuma、Makoto Wada

  DOI：10.1246/bcsj.73.689

  日期：2000.3

  A convenient one pot allylation of aldehydes with allylic iodides prepared in situ from allylic alcohols by using trimethylsilyl chloride and sodium iodide proceeds smoothly in the presence of meta...

  醛与烯丙基碘的方便的单锅烯丙基化反应，在间苯二甲酸存在下，使用三甲基氯硅烷和碘化钠由烯丙醇原位制备。
• Charge reversal of electrophilic π-allylpalladium intermediates; carbonyl allylation by allylic acetates with PdCl₂(PhCN)₂–SnCl₂
  作者：Yoshiro Masuyama、Ryoji Hayashi、Kiyotaka Otake、Yasuhiko Kurusu

  DOI：10.1039/c39880000044

  日期：——

  Carbonyl allylation by stable allylic acetates with Pd0–SnCl2 occurred regio-, chemo-, and diastereoselectively to afford the corresponding homoallylic alcohols.

  稳定的烯丙基乙酸与Pd 0 -SnCl 2的羰基烯丙基化发生区域，化学和非对映选择性，得到相应的均烯丙基醇。
• Conversion of Hydroxyl Groups in Alcohols to Other Functional Groups with<i>N</i>-Hydroxy-2-thiopyridone, and Its Application to Dialkylamines and Thiols
  作者：Hideo Togo、Misa Fujii、Masataka Yokoyama

  DOI：10.1246/bcsj.64.57

  日期：1991.1

  The radical decarboxylation reaction of N-alkoxyoxalyloxy-2-thiopyridone which was prepared by the reaction of alcohol, oxalyl chloride, and N-hydroxy-2-thiopyridone was studied both in the absence and presence of olefinic compounds. The same reactions with olefinic and acetylenic alcohols gave the corresponding lactone derivatives. On the other hand the unsymmetrical alkyl 2-pyridyl disulfides were obtained by the same reaction with aliphatic thiols.

  对由醇、草酰氯和N-羟基-2-噻吩酮反应制备的N-烷氧基草酰氧基-2-噻吩酮的还原脱羧反应进行了研究，无论是在没有还是有烯烃化合物存在的情况下。同样，与烯醇和炔醇的反应得到了相应的内酯衍生物。另一方面，通过与脂肪族硫醇的相同反应得到了不对称的烷基-2-吡啶基二硫化物。
• Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl₃
  作者：Josefa L. López-Martínez、Irene Torres-García、Ignacio Rodríguez-García、Manuel Muñoz-Dorado、Miriam Álvarez-Corral

  DOI：10.1021/acs.joc.8b02643

  日期：2019.1.18

  CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N·HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis

  CpTiCl 2，由锰还原CpTiCl的原位制备3，是用于羰基化合物的巴比尔型烯丙基炔丙基和优异的新系统。与再生系统Et 3 N·HBr / TMSBr结合使用时，可以催化量使用。该系统显示的高区域选择性和立体选择性使其可用于天然产物合成中的异戊二烯化和丁二酰化过程。