2-methyltridec-1-en-4-ol | 197581-75-2

• 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: 2-methyltridec-1-en-4-ol
• CAS: 197581-75-2
• 化学式: C₁₄H₂₈O
• 分子量: 212.376
• InChiKey: YZDPWKWSGRWVHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  2-methyltridec-1-en-4-ol 在 4-二甲氨基吡啶 、 potassium fluoride 、 正丁基锂 、 Cp2Ti(P(OEt)3)2 、 双氧水 、 potassium hydrogencarbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 正己烷 、 丙酮 为溶剂， 反应 33.5h， 生成 (Z)-1,5-diacetoxy-3-methyl-2-tetradecene
  参考文献：
  名称：

  钛茂（II）促进的具有末端碳-碳双键的硫缩醛的环化反应制备（Z）-Alk-2-ene-1,5-二醇

  摘要：

  由[2,2-双（苯硫基）乙基]（丁-3-烯氧基）二甲基硅烷或3的二甲基（丙-2-烯基）甲硅烷基醚制得的钛茂金属（II）促进的钛卡宾配合物的闭环易位， 3-双（苯硫基）丙醇制得七元环状不饱和甲硅烷基醚。环状甲硅烷基醚的硅碳键的氧化裂解产生具有高Z立体选择性的烯烃二醇。

  DOI：

  10.1002/1099-0690(200101)2001:1<155::aid-ejoc155>3.0.co;2-#
• 作为产物：
  描述：

  癸醛 、 2-Methylallylmagnesium Chloride 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-methyltridec-1-en-4-ol
  参考文献：
  名称：

  FeCl 3 ·6H 2 O，由N-保护的δ-羟基氨基烯丙基乙酸酯非对映选择性合成顺式-异恶唑烷的催化剂

  摘要：

  描述了通过FeCl 3 ·6H 2 O-催化的δ-羟基氨基烯丙基乙酸酯环化的顺式-3,5-二取代的异恶唑烷的环保和非对映选择性合成。通过制备几种功能化的1,3-氨基醇前体，突出了这些产品的合成潜力。

  DOI：

  10.1021/jo401627p

文献信息

• Allylation of Carbonyl Compounds with Allylic Gallium Reagents
  作者：Takashi Tsuji、Shin-ichi Usugi、Hideki Yorimitsu、Hiroshi Shinokubo、Seijiro Matsubara、Koichiro Oshima

  DOI：10.1246/cl.2002.2

  日期：2002.1

  Allylic gallium reagents, prepared from gallium trichloride and the corresponding allylic Grignard reagents, allylated carbonyl compounds in good yields in an aqueous medium as well as in organic solvent.

  烯丙基镓试剂，由三氯化镓与相应的烯丙基格氏试剂制备而来，在水中及有机溶剂中均能以良好产率使羰基化合物发生烯丙基化反应。
• Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor
  作者：Andrea D'Annibale、Laura Ciaralli、Mauro Bassetti、Chiara Pasquini

  DOI：10.1021/jo070600h

  日期：2007.8.1

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.
• SmI₂-Induced 2,3-Wittig Rearrangement:  Regioselective Generation of α-Allyloxy Carbanions via 1,5-Hydrogen Transfer of Vinyl Radicals
  作者：Munetaka Kunishima、Kazuhito Hioki、Kazuhiro Kono、Akira Kato、Shohei Tani

  DOI：10.1021/jo9714223

  日期：1997.10.1
• FeCl₃·6H₂O, a Catalyst for the Diastereoselective Synthesis of <i>cis</i>-Isoxazolidines from <i>N</i>-Protected δ-Hydroxylamino Allylic Acetates
  作者：Johan Cornil、Amandine Guérinot、Sébastien Reymond、Janine Cossy

  DOI：10.1021/jo401627p

  日期：2013.10.18

  isoxazolidines through the FeCl3·6H2O-catalyzed cyclization of δ-hydroxylamino allylic acetates is described. The synthetic potential of these products is highlighted by the preparation of several functionalized 1,3-amino alcohol precursors.

  描述了通过FeCl 3 ·6H 2 O-催化的δ-羟基氨基烯丙基乙酸酯环化的顺式-3,5-二取代的异恶唑烷的环保和非对映选择性合成。通过制备几种功能化的1,3-氨基醇前体，突出了这些产品的合成潜力。
• Preparation of ( <i>Z</i> )‐Alk‐2‐ene‐1,5‐diols by the Titanocene(II)‐Promoted Cyclization of Thioacetals Possessing a Terminal Carbon−Carbon Double Bond
  作者：Tooru Fujiwara、Kenjirou Yanai、Keiko Shimane、Mayumi Takamori、Takeshi Takeda

  DOI：10.1002/1099-0690(200101)2001:1<155::aid-ejoc155>3.0.co;2-#

  日期：2001.1

  Titanocene(II)-promoted ring-closing metathesis of the titanium carbene complexes prepared from [2,2-bis(phenylthio)ethyl](but-3-enyloxy)dimethylsilanes or dimethyl(prop-2-enyl)silyl ethers of 3,3-bis(phenythio)propanols gave seven-membered cyclic unsaturated silyl ethers. Oxidative cleavage of a silicon−carbon bond of the cyclic silyl ethers resulted in olefinic diols, with high Z stereoselectivity.

  由[2,2-双（苯硫基）乙基]（丁-3-烯氧基）二甲基硅烷或3的二甲基（丙-2-烯基）甲硅烷基醚制得的钛茂金属（II）促进的钛卡宾配合物的闭环易位， 3-双（苯硫基）丙醇制得七元环状不饱和甲硅烷基醚。环状甲硅烷基醚的硅碳键的氧化裂解产生具有高Z立体选择性的烯烃二醇。