(3Z)-3-(chloromethyl)-4-(4-methylphenyl)but-3-en-2-one | 232944-73-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (3Z)-3-(chloromethyl)-4-(4-methylphenyl)but-3-en-2-one
• 英文别名: (Z)-3-(chloromethyl)-4-(4-methylphenyl)but-3-en-2-one
• CAS: 232944-73-9
• 化学式: C₁₂H₁₃ClO
• 分子量: 208.688
• InChiKey: UQLCAHRYENRPBP-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙烯腈 、 (3Z)-3-(chloromethyl)-4-(4-methylphenyl)but-3-en-2-one 在 三乙烯二胺 作用下， 反应 168.0h， 以40%的产率得到2-acetyl-3-(4-methylphenyl)-4-cyanopenta-1,4-diene
  参考文献：
  名称：

  Baylis–Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes

  摘要：

  A novel synthesis of functionalized 1,4-pentadienes via the reaction of acrylonitrile with allyl halides, derived from Baylis-Hillman adducts, in the presence of DABCO has been described, demonstrating for the first time the application of allyl halides as electrophiles in the Baylis-Hillman reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01886-4
• 作为产物：
  描述：

  3-Buten-2-one, 3-[(acetyloxy)(4-methylphenyl)methyl]- 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到(3Z)-3-(chloromethyl)-4-(4-methylphenyl)but-3-en-2-one
  参考文献：
  名称：

  FeCl3 和 Yb(OTf)3 介导的 Baylis-Hillman 加合物的乙酸酯转化为 (Z) 和 (E) 三取代烯烃

  摘要：

  摘要 无水 FeCl3 和 Yb(OTf)3 被用作新试剂，分别将 Baylis-Hillman 加合物的乙酸酯立体选择性异构化为 (Z) 和 (E) 三取代烯烃。

  DOI：

  10.1081/scc-120027238

文献信息

• The Baylis-Hillman reaction: An expedient synthesis of (Z)-keto allyl bromides and chlorides
  作者：Deevi Basavaiah、Rachakonda Suguna Hyma、Kisari Padmaja、Marimganti Krishnamacharyulu

  DOI：10.1016/s0040-4020(99)00326-9

  日期：1999.5

  A simple and expedient synthesis of (Z)-keto allyl bromides and chlorides, from the Baylis-Hillman adducts is described.

  描述了从Baylis-Hillman加合物简单且方便地合成（Z）-酮烯丙基溴和氯化物。
• Dimethyl sulfide–boron trihalide-mediated reactions of α,β-unsaturated ketones with aldehydes: one-pot synthesis of Baylis–Hillman adducts and α-halomethyl enones
  作者：Tatsunori Iwamura、Masaru Fujita、Tetsuya Kawakita、Sayaka Kinoshita、Shin-ichi Watanabe、Tadashi Kataoka

  DOI：10.1016/s0040-4020(01)00842-0

  日期：2001.10

  The reactions of aldehydes with 3-buten-2-one (2) were conducted in the presence of (BBr3Me2S)-Me-. or BCl3-Me2S and then worked up with aqueous NaHCO3, affording the a-methylene aldol 3, (alpha -halomethyl aldol 4 or 6, and a-halomethyl enones 5 or 7, respectively. In contrast, the reactions quenched with water gave the alpha -halomethyl enones 5 or 7 in high yields, while the work-up with an aqueous 10% trimethylamine gave the alpha -methylene aldol 3. The phenol 15 and half-acetal 16 were obtained from the reaction of p-nitrobenzaldehyde (1a) with cyclohexenone (10). (C) 2001 Elsevier Science Ltd. All rights reserved.
• FeCl₃and Yb(OTf)₃Mediated Conversion of Acetates of the Baylis–Hillman Adducts into (Z) and (E) Trisubstituted Alkenes
  作者：Palakodety Radha Krishna、V. Kannan、G. V. M. Sharma

  DOI：10.1081/scc-120027238

  日期：2004.12.31

  Abstract Anhydrous FeCl3 and Yb(OTf)3 are utilised as new reagents for the stereoselective isomerisation of acetates of the Baylis–Hillman adducts to both (Z) and (E) trisubstituted alkenes respectively.

  摘要 无水 FeCl3 和 Yb(OTf)3 被用作新试剂，分别将 Baylis-Hillman 加合物的乙酸酯立体选择性异构化为 (Z) 和 (E) 三取代烯烃。
• Baylis–Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes
  作者：Deevi Basavaiah、Nagaswamy Kumaragurubaran、Duddu S Sharada

  DOI：10.1016/s0040-4039(00)01886-4

  日期：2001.1

  A novel synthesis of functionalized 1,4-pentadienes via the reaction of acrylonitrile with allyl halides, derived from Baylis-Hillman adducts, in the presence of DABCO has been described, demonstrating for the first time the application of allyl halides as electrophiles in the Baylis-Hillman reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.