1-chloromethyl-1-phenylbut-3-en-1-ol | 79786-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-chloromethyl-1-phenylbut-3-en-1-ol
• 英文别名: 1-chloro-2-phenylpent-4-en-2-ol；1-chloro-2-phenyl-pent-4-en-2-ol；(+/-)-1-Chlor-2-hydroxy-2-phenyl-penten-(4)；1-Chlor-2-phenyl-pent-4-en-2-ol
• CAS: 79786-73-5
• 化学式: C₁₁H₁₃ClO
• 分子量: 196.677
• InChiKey: ZHZUCOCIGXYPIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  309.9±37.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-chloromethyl-1-phenylbut-3-en-1-ol 在 正丁基锂 、 naphthalen-1-yl-lithium 作用下， 以 乙醚 为溶剂， 生成 methyl 3-hydroxy-3-phenylhex-5-enoate
  参考文献：
  名称：

  Barluenga, Jose; Florez, Josefa; Yus, Miguel, Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 3019 - 3026

  摘要：

  DOI：
• 作为产物：
  描述：

  alpha-氯乙酰苯 、 3-氯丙烯 在 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以81%的产率得到1-chloromethyl-1-phenylbut-3-en-1-ol
  参考文献：
  名称：

  介孔材料 (MCM-41) 负载的氰基钯配合物催化醛和酮烯丙基化合成高烯丙醇

  摘要：

  使用 SnCl2 作为还原剂，通过 MCM-41 负载的氰基钯配合物在 DMF 中催化醛和酮与烯丙基氯的烯丙基化，可以方便地合成多种高收率的高收率的高烯丙醇。这种聚合钯配合物可以回收并重新使用，但会损失一些活性。

  DOI：

  10.3184/030823409x460911

文献信息

• Indium-mediated allylation reactions of α-chlorocarbonyl compounds and preparation of allylic epoxides
  作者：Jeong Ah Shin、Kyung Il Choi、Ae Nim Pae、Hun Yeong Koh、Han-Young Kang、Yong Seo Cho

  DOI：10.1039/b101111l

  日期：——

  Indium-mediated allylation of α-chlorocarbonyl compounds with various allyl bromides in aqueous media gave the corresponding homoallylic chlorohydrins, which could be transformed into the corresponding epoxides in the presence of a base. These reactions were strongly dependent upon both the substituents at the carbon bearing chlorine and the allyl bromides used.

  在水介质中铟介导的α-氯羰基化合物与各种烯丙基溴的烯丙基化反应生成相应的均烯丙基氯醇，可将其转化为相应的烯丙基氯醇。 环氧化物在基地的情况下。这些反应强烈地依赖于含碳的氯上的取代基和所用的烯丙基溴。
• Process for producing propargylcarbinol compounds
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0404077A1

  公开（公告）日：1990-12-27

  Process for producing a propargylcarbinol compound of general formula (I): where R¹ and R² independently represent hydrogen; C₁-C₁₅ alkyl which may be substituted with one or more halogen, hydroxyl, phenyl, phenoxy, phenyl or phenoxy substituted with one or more halogen, hydroxyl, alkoxy, phenoxy, dialkylamino and/or methylenedioxy aralkyloxy, dialkylamino, alkylthio, phenylthio, biphenyl and/or phenylalkyl; C₂-C₁₅ alkenyl which may be substituted with one or more halogen, hydroxyl, phenyl, phenoxy, phenyl or phenoxy substituted with one or more halogen, hydroxyl, alkoxy, phenoxy, dialkylamino and/or methylenedioxy, dialkylamino alkylthio, phenylthio, biphenyl and/or phenylalkyl; C₂-C₁₅ alkynyl which may be substituted with one or more halogen, hydroxyl, phenyl, phenoxy, phenyl or phenoxy substituted with one or more halogen, hydroxyl, alkoxy, phenoxy, dialkylamino and/or methylenedioxy, dialkylamino, alkylthio, phenylthio, biphenyl and/or phenylalkyl; C₃-C₁₅ cycloalkyl; C₄-C₁₅ cycloalkenyl; or phenyl, naphthyl, furyl or thienyl which may be substituted with one or more halogen, hydroxyl, alkyl, alkoxy, phenoxy, dialkylamino and/or methylenedioxy; or R¹ and R² together represent C₂-C₁₅ alkylene or alkenylene; with proviso that carbon atoms in the 1-positions of R¹ and R² are not together tertiary carbon atoms and that if one of R¹ and R² is furyl, the other does not represent hydrogen: which comprises reacting a haloallylcarbinol compound of the formula (II): wherein R¹ and R² are as defined above and X² represents chlorine, bromine or iodine, with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargyl carbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.

  生产通式(I)的丙炔基甲醇化合物的工艺： 其中 R¹ 和 R² 独立地代表氢；C₁-C₁₅烷基，可被一个或多个卤素、羟基、苯基、苯氧基、苯基或苯氧基取代；C₂-C₁₅烯基，可被一个或多个卤素、羟基、烷氧基、苯氧基、二烷基氨基和/或亚甲基二氧基烷氧基、二烷基氨基、烷硫基、苯硫基、联苯基和/或苯基烷基取代；C₂-C₁₅烯基，可被一个或多个卤素、羟基、苯基、苯氧基、被一个或多个卤素、羟基、烷氧基、苯氧基、二烷基氨基和/或亚甲基二氧基、二烷基氨基烷硫基、苯硫基、联苯基和/或苯基烷基取代；C₂-C₁₅炔基，可被一个或多个卤素、羟基、苯基、苯氧基、苯基或被一个或多个卤素、羟基、烷氧基、苯氧基、二烷基氨基和/或亚甲基二氧基、二烷基氨基、烷硫基、苯硫基、联苯基和/或苯基烷基取代；C₃-C₁₅ 环烷基； C₄-C₁₅ 环烯基；或苯基、萘基、呋喃基或噻吩基，可被一个或多个卤素、羟基、烷基、烷氧基、苯氧基、二烷基氨基和/或亚甲基二氧基取代；或 R¹ 和 R² 共同代表 C₂-C₁₅亚烷基或烯基；但 R¹ 和 R² 的 1 位上的碳原子不能同时为叔碳原子，且如果 R¹ 和 R² 中的一个为呋喃基，则另一个不代表氢： 其中包括使式(II)的卤代烯丙基甲醇化合物反应： 其中 R¹ 和 R² 如上定义，X² 代表氯、溴或碘，与碱反应。本发明还涉及生产卤代烯丙基甲醇化合物的工艺。上述丙炔基甲醇化合物可用作农用化学品、药品、香水、树脂单体等的中间体。
• Mild and General Zinc-Alkoxide-Catalyzed Allylations of Ketones with Allyl Pinacol Boronates
  作者：Keith R. Fandrick、Daniel R. Fandrick、Joe J. Gao、Jonathan T. Reeves、Zhulin Tan、Wenjie Li、Jinhua J. Song、Bruce Lu、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol101301s

  日期：2010.9.3

  A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.
• Carbonyl allylation of aldehydes and ketones with allylic chlorides catalyzed by immobilization of palladium in MCM-41
  作者：Hong Zhao、Jian Peng、Ruian Xiao、Wenyan Hao、Ming-Zhong Cai

  DOI：10.1016/j.jorganchem.2010.10.055

  日期：2011.5

  The heterogeneous carbonyl allylation of aldehydes and ketones with allylic chlorides was achieved in DMF using SnCl2 as reducing agent at 25-40 degrees C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(II)], yielding a variety of homoallylic alcohols in good to high yields. This heterogeneous palladium catalyst exhibited higher activity than (N-propylethylenediamine) PdCl2 and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 5 consecutive trials without any decreases in activity. (C) 2010 Elsevier B.V. All rights reserved.
• Cai, Ming-Zhong; Song, Cai-Sheng; Huang, Xian, Synthetic Communications, 1997, vol. 27, # 17, p. 3087 - 3093
  作者：Cai, Ming-Zhong、Song, Cai-Sheng、Huang, Xian

  DOI：——

  日期：——