4-(p-Chlorophenyl)-2-hydroxy-2-methyl-3-butene | 77144-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 4-(p-Chlorophenyl)-2-hydroxy-2-methyl-3-butene
• 英文别名: trans-4-(4-chlorophenyl)-2-methylbut-3-en-2-ol；(E)-4-(4-chlorophenyl)-2-methylbut-3-en-2-ol；2-methyl-4-(4-chlorophenyl)-3-butene-2-ol；4-(4-chlorophenyl)-2-methyl-3-butenol-2
• CAS: 77144-21-9
• 化学式: C₁₁H₁₃ClO
• 分子量: 196.677
• InChiKey: ZHXRHLXKNRBBSP-BQYQJAHWSA-N

物化性质

• 熔点：
  65-67 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  316.1±22.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 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：

  4-(p-Chlorophenyl)-2-hydroxy-2-methyl-3-butene 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以57%的产率得到2-methyl-4-(4-chlorophenyl)-3,4-epoxybutane-2-ol
  参考文献：
  名称：

  Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides

  摘要：

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.032
• 作为产物：
  描述：

  3-甲基-1-(4-氯苯基)-2-丁烯醇 在 Crabtree's catalyst 作用下， 以 2-甲基四氢呋喃 为溶剂， 以94 %的产率得到4-(p-Chlorophenyl)-2-hydroxy-2-methyl-3-butene
  参考文献：
  名称：

  铱催化的烯丙醇 1,3-重排

  摘要：

  实现了有效的 Ir(III) 二氢化物络合物催化烯丙醇的 1,3-重排，从容易获得的起始材料中以高收率区域选择性和立体选择性地提供相应的不易获得的烯丙醇。反应途径涉及 π-烯丙基-Ir(V) 中间体，Ir(III) 二氢化物络合物中的二氢化物作为氢开关调节铱中心的化合价。

  DOI：

  10.1002/chem.202300027

文献信息

• Copper-Catalyzed Reductive Ireland–Claisen Rearrangements of Propargylic Acrylates and Allylic Allenoates
  作者：Siyuan Guo、Kong Ching Wong、Stephan Scheeff、Zhuo He、Wesley Ting Kwok Chan、Kam-Hung Low、Pauline Chiu

  DOI：10.1021/acs.joc.1c02455

  日期：2022.1.7

  The copper-catalyzed reductive Ireland–Claisen rearrangement of propargylic acrylates led to 3,4-allenoic acids. The use of silanes or pinacolborane as stoichiometric reducing agents and triethylphosphite as a ligand facilitated the divergent and complementary selectivity for the synthesis of diastereomeric anti- and syn-rearranged products, respectively. Copper-catalyzed reductive Ireland–Claisen rearrangement

  炔丙基丙烯酸酯的铜催化还原爱尔兰-克莱森重排产生 3,4-丙二烯酸。硅烷或频哪醇硼烷作为化学计量还原剂和亚磷酸三乙酯作为配体的使用促进了合成非对映体反-和顺的发散和互补选择性-重新排列的产品，分别。仅当频哪醇硼烷用作还原剂以优异的收率和在某些情况下具有良好的非对映选择性时，铜催化的还原爱尔兰-克莱森重排才能有效地进行烯丙基 2,3-烯丙酸酯。机理研究表明，甲硅烷基和硼烯醇化物，而不是铜烯醇化物，通过椅状过渡态进行立体定向重排，得到相应的克莱森重排产物。
• Photochemical Intermolecular Cyclopropanation Reactions of Allylic Alcohols for the Synthesis of [3.1.0]-Bicyclohexanes
  作者：Chao Pei、Claire Empel、Rene M. Koenigs

  DOI：10.1021/acs.orglett.2c04010

  日期：2023.1.13

  highly desirable in drug and natural products synthesis. Herein, we report on a photochemical, chemoselective reaction of aryldiazoacetates with allylic alcohols that furnishes cyclopropane-fused lactone skeletons efficiently in one step. The diastereoselectivity of the protocol was precisely controlled, and chemoselective cyclopropanation of allylic alcohols via free carbene intermediate followed by transesterification

  环丙烷稠合内酯在药物和天然产物合成中非常受欢迎。在此，我们报告了芳基重氮乙酸酯与烯丙醇的光化学化学选择性反应，该反应可一步有效地提供环丙烷稠合的内酯骨架。该方案的非对映选择性得到精确控制，通过游离卡宾中间体对烯丙醇进行化学选择性环丙烷化，然后进行酯交换反应，可通过典型的 O-H 插入反应以高产率生成一系列双环内酯，而不会形成醚副产物。
• A STEREOSELECTIVE SYNTHESIS OF UNSATURATED PHOSPHONATES BY WITTIG-HORNER REACTIONS OF BISPHOSPHONYLMETHANE WITH 5-ARYL-(3-METHYL)-2E,4E-PENTADIENALS
  作者：De Qing Shi、Ru Yu Chen

  DOI：10.1080/10426500008045248

  日期：2000.1

  A new type of unsaturated phosphonates 5 were synthesized by the Wittig-Horner reactions of bisphosphonylmethane 4 with 5-aryl-2(E),4(E)-pentadienal and 5-aryl-3-methyl-2(E), 4(E)-pentadienal. The structures of all new compounds prepared were characterized by H-1 NMR, P-31 NMR, C-13 NMR, IR spectra, MS and elemental analyses, one of them was determined by X-ray diffraction analysis.
• One-Step Vilsmeier Route to Some 5-Aryl-3-methyl-2(<i>E</i>),4(<i>E</i>)-pentadienals and their Oxidation to Pentadienoic Acids
  作者：M. Parameswara Reddy、G. S. Krishna Rao

  DOI：10.1055/s-1980-29219

  日期：——
• Copper-Catalyzed Alkenylation of Alcohols with β-Nitrostyrenes via a Radical Addition–Elimination Process
  作者：Yan-qin Yuan、Sheng-rong Guo

  DOI：10.1055/s-0034-1380445

  日期：——

  A new method for the preparation of allylic alcohol derivatives has been developed via a radical mechanism using DTBP as the radical initiator promoted by copper salt. The C(sp(3))-H bond in various alcohols, toluene derivatives, and alkanes were successfully converted into C-C bonds to yield the desired products in moderate to good yields.