3-methoxy-1-nonene | 94904-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-1-nonene
• 英文别名: 1-Nonen-3-ol, methyl ether；3-methoxynon-1-ene
• CAS: 94904-66-2
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: RSKWWTZKISOAHR-UHFFFAOYSA-N

物化性质

• 沸点：
  185.0±9.0 °C(Predicted)
• 密度：
  0.799±0.06 g/cm3(Predicted)
• 保留指数：
  1122.1

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  甲醇 、 3-methoxy-1-nonene 在 sodium hydroxide 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以63%的产率得到methyl 2-methoxyoctanoate
  参考文献：
  名称：

  Oxidative cleavage of mono-, di-, and trisubstituted olefins to methyl esters through ozonolysis in methanolic sodium hydroxide

  摘要：

  The ozonolysis of alkenes in methanolic NaOH or NaOMe with CH2Cl2 as cosolvent leads directly to methyl esters. The procedure has been used to prepare various alpha-, beta, and omega-alkoxy esters, acyloxy esters, and alpha- and beta-N-acyl and N-sulfonyl esters from the appropriate unsaturated ethers, esters, and amides. Other examples include the formation of dimethyl octanedioate from cyclooctene (75% yield), dimethyl nonanedioate and methyl nonanoate from methyl oleate (77 and 78%, respectively), and tetradecanoic acid gamma-lactone from 2-methyl-2-hexadecen-6-ol (80% yield).

  DOI：

  10.1021/jo00066a019
• 作为产物：
  描述：

  庚醛 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 17.0h， 生成 3-methoxy-1-nonene
  参考文献：
  名称：

  铁催化的格氏交叉偶联与烯丙基甲基醚或烯丙基三甲基甲硅烷基醚

  摘要：

  我们发现芳基格氏试剂和烯丙基甲基醚之间的交叉偶联在催化量的 Fe(acac)3 存在下进行得很好，以良好的产率提供相应的烯丙基取代产物。在相同条件下，烯丙基三甲基甲硅烷基醚也与格氏试剂反应，得到相应的交叉偶联产物。

  DOI：

  10.1055/s-0036-1591774

文献信息

• Carbon–Carbon Bond Formation by the Use of Chloroiodomethane as a C₁Unit. II. The Preparation and Synthetic Application of 1-Chloro-3-iodoheptane
  作者：Sotaro Miyano、Hiroshi Hokari、Yoshiharu Umeda、Harukichi Hashimoto

  DOI：10.1246/bcsj.53.770

  日期：1980.3

  Terminal alkenes, R–CH=CH2 (R=Et, n-Pr, n-Bu, n-Hex), were readily transformed into 1-chloro-3-iodoalkanes by the AIBN-induced free radical addition of chloroiodomethane. Thus, 1-chloro-3-iodoheptane was obtained from 1-hexene in an 88% yield; this in turn was allowed to react with dialkyl malonates in the presence of alkoxides in alcohols to give dialkyl 2-butylcyclobutane-1,1-dicarboxylates and dialkyl

  通过 AIBN 诱导的氯碘甲烷自由基加成，末端烯烃 R–CH=CH2（R=Et、n-Pr、n-Bu、n-Hex）很容易转化为 1-chloro-3-iodoalkanes。因此，1-氯-3-碘庚烷以88%的产率从1-己烯得到；在醇中的醇盐存在下，这又使其与丙二酸二烷基酯反应，得到 2-丁基环丁烷-1,1-二羧酸二烷基酯和 (E)-3-辛烯-1,1-二羧酸二烷基酯 (7)，可以通过选择实验参数优先获得。烯烃产物7进一步用于合成(E)-5-癸烯乙酸酯和/或1,4-壬内酯。
• Regio- and stereoselective carbon-carbon bond formation through transition metal catalysis. The influence of catalyst chirality on selective ethylmagnesiation of chiral, nonracemic alcohols and ethers
  作者：Amir H. Hoveyda、James P. Morken

  DOI：10.1021/jo00068a018

  日期：1993.7

  Reaction of chiral zirconium dichloride 1 with EtMgCl leads to the formation of (R)-2. The transition metal-alkene complex 2 may then be employed as an effective catalyst in ethylmagnesations of nonracemic allylic alcohols and ethers. These transformations proceed with varying levels of diastereochemical control, depending on which antipode of the chiral substrate is employed. The difference between the stereo- and regiochemical outcome in reactions catalyzed by the achiral CP2ZrCl2 and 1, the variable sensitivity of these sets of reactions to competing ligating Lewis basic solvents, and the influence of the reaction temperature on the regiochemical outcome of carbometalation is described. These data provide important insights into various mechanistic aspects of the carbomagnesation process.
• MIYANO SOTARO; HOKARI HIROSHI; UMEDA YOSHIHARU; HASHIMOTO HARUKICHI, BULL. CHEM. SOC. JAP., 1980, 53, NO 3, 770-774
  作者：MIYANO SOTARO、 HOKARI HIROSHI、 UMEDA YOSHIHARU、 HASHIMOTO HARUKICHI

  DOI：——

  日期：——
• KLUNDER, J. M.;CARON, M.;UCHIYAMA, MAMORU;SHARPLESS, K. B., J. ORG. CHEM., 1985, 50, N 6, 912-915
  作者：KLUNDER, J. M.、CARON, M.、UCHIYAMA, MAMORU、SHARPLESS, K. B.

  DOI：——

  日期：——
• Iron-Catalyzed Grignard Cross-Couplings with Allylic Methyl Ethers or Allylic Trimethylsilyl Ethers
  作者：Chika Seto、Takeshi Otsuka、Yoshiki Takeuchi、Daichi Tabuchi、Takashi Nagano

  DOI：10.1055/s-0036-1591774

  日期：2018.6

  We have found that cross-coupling between aryl Grignard reagents and allylic methyl ethers proceeded well in the presence of a catalytic amounts of Fe(acac)3 to afford the corresponding allylic substitution products in good yields. Under the same conditions, allylic trimethylsilyl ethers also reacted with Grignard reagents to give the corresponding cross-coupling products.

  我们发现芳基格氏试剂和烯丙基甲基醚之间的交叉偶联在催化量的 Fe(acac)3 存在下进行得很好，以良好的产率提供相应的烯丙基取代产物。在相同条件下，烯丙基三甲基甲硅烷基醚也与格氏试剂反应，得到相应的交叉偶联产物。