(Z)-chloro-1-phenyl-4-butene-1-ol-4 | 84491-06-5

• 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: (Z)-chloro-1-phenyl-4-butene-1-ol-4
• 英文别名: (Z)-4-chloro-1-phenyl-3-buten-1-ol；Z-4-chloro-1-phenylbut-3-en-1-ol；(Z)-4-chloro-1-phenylbut-3-en-1-ol
• CAS: 84491-06-5
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: HWEIMQDNNDIROJ-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯甲醛 、 2-(1-chloro-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 生成 (Z)-chloro-1-phenyl-4-butene-1-ol-4
  参考文献：
  名称：

  HOFFMANN, R. W.;LANDMANN, B., CHEM. BER., 1986, 119, N 3, 1039-1053

  摘要：

  DOI：

文献信息

• Action du chloroallyllithium sur les aldehydes et les cetones: synthese en une etape d'alcools β-ethyleniques γ-chlores de configuration z et d'epoxydes α-ethyleniques bi- ou tri-substitues
  作者：A. Doucoure、B. Mauze、L. Miginiac

  DOI：10.1016/s0022-328x(00)87068-0

  日期：1982.9

  Chloroallyllithium readily reacts with aliphatic and aromatic aldehydes and ketones to produce, in a one-step reaction, Z-γ-chlorinated-β-ethylenic alcohols and bi- or tri-substituted epoxides.

  氯代烯丙基锂易于与脂族和芳族醛和酮反应，以一步反应生成Z -γ氯化的β-乙烯醇和双或三取代的环氧化物。
• Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis
  作者：Ming Joo Koh、Thach T. Nguyen、Hanmo Zhang、Richard R. Schrock、Amir H. Hoveyda

  DOI：10.1038/nature17396

  日期：2016.3.24

  halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of a catalyst that is generated in situ and used with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents, and proceed to high

  烯烃复分解对现代有机化学产生了很大的影响，但仍然存在重要的缺点：例如，缺乏可用于生成无环烯基卤化物的有效工艺。卤代钌卡宾配合物分解迅速或提供低活性和/或最小的立体选择性，我们对相应的高氧化态系统的理解是有限的。在这里，我们展示了以前未知的卤代钼亚烷基物质具有异常的反应性，并且能够参与提供无环 1,2-二取代 Z-烯基卤化物的高产烯烃复分解反应。原位生成的少量催化剂可促进转化，并与未纯化、市售且易于处理的液体 1,2-二卤代乙烯试剂一起使用，并在四小时内在常温下进行高转化率。我们以高达 91% 的收率和完全的 Z 选择性获得了许多链烯基氯、溴化物和氟化物。该方法可用于轻松合成生物活性化合物，以及对复杂有机分子进行位点和立体选择性氟化。
• Chloroallyl anion : Highly regio- and diastereoselective α-addition of chloroallyl zinc reagent to carbonyl compounds
  作者：K. Mallaiah、J. Satyanarayana、H. Ila、H. Junjappa

  DOI：10.1016/s0040-4039(00)93402-6

  日期：1993.5

  The chloroallyl zinc reagent generated insitu by deprotonation of allyl chloride in the presence of lithium diisopropylamide and zinc chloride undergoes highly regio- and diastereoselective α-addition to carbonyl compounds to give syn chlorohydrins which on treatment with base afford cis vinyloxiranes in high yields.

  在二异丙基氨基化锂和氯化锌的存在下通过烯丙基氯的去质子化而原位生成的氯代烯丙基锌试剂经过高度区域和非对映选择性的α-加成反应生成羰基化合物，经碱处理后可以合成高产顺式乙烯基氧杂环丁烷。
• Diastereo- and Enantioselective Synthesis of <i>syn</i>-α-Vinylchlorohydrins and <i>cis</i>-Vinylepoxides
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1021/jo960875p

  日期：1996.1.1

  A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF3 . OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de greater than or equal to 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-alpha a-halohydrins (de greater than or equal to 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-gamma-chloroallyl]BIpc(2) leads to chiral syn-alpha-chlorohydrins and cis-vinylepoxides in high de (greater than or equal to 90%) and ee(90-99%). Enantioselectivity of reactions of chiral (Z)-(gamma-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other alpha-or gamma-substituted allylboranes. The effects of proportion ofBF(3) . OEt(2) and the relative efficacies of LiNR(2) bases on diastereo- and enantioselectivity of the chloroallylation are reported.
• Julia, Marc; Verpeaux, Jean-Noel; Zahneisen, Thomas, Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 539 - 554
  作者：Julia, Marc、Verpeaux, Jean-Noel、Zahneisen, Thomas

  DOI：——

  日期：——